[{"_1":2,"_3":-5,"_4":-5},"loaderData",{"_5":6,"_7":8},"actionData","errors","root",{"_139":-5,"_140":-5,"_141":142,"_143":144,"_145":146},"routes/clips.$id.$slug",{"_9":10,"_11":12},"clip",{"_13":14,"_15":16,"_17":-5,"_18":19,"_20":-5,"_21":22,"_23":24,"_25":26,"_27":28,"_29":30,"_31":32,"_33":34,"_35":36,"_37":38,"_39":40,"_41":-5,"_42":-5,"_43":-5,"_44":45,"_46":-5,"_47":48,"_49":50,"_51":-5},"canonicalUrl","https://howleaderslead.com/clips/3036/even-top-leaders-are-still-figuring-stuff-out","id",3036,"title","Even top leaders are still figuring stuff out","subtitle","transcript","WEBVTT\n\n1\n00:00:00.000 --> 00:00:02.840\nWhat did you learn by being in a consultant?\n\n2\n00:00:02.840 --> 00:00:04.740\n- You know, I'll share this lesson with you.\n\n3\n00:00:04.740 --> 00:00:07.000\nI don't know how appealing it will be to people,\n\n4\n00:00:07.000 --> 00:00:09.720\nbut actually it was such an incredible experience\n\n5\n00:00:09.720 --> 00:00:14.200\nto be 21, 22 years old and asked to go in\n\n6\n00:00:14.200 --> 00:00:16.040\nand work with some of the biggest companies in the world\n\n7\n00:00:16.040 --> 00:00:19.400\non core strategic problems that they were struggling with,\n\n8\n00:00:19.400 --> 00:00:20.720\nthat they did not have answers to.\n\n9\n00:00:20.720 --> 00:00:23.720\nAnd that was exactly why we were there as a firm\n\n10\n00:00:23.720 --> 00:00:26.660\nand why I was being asked to do analysis or research\n\n11\n00:00:26.660 --> 00:00:29.600\nor prepare a presentation that summarized various things.\n\n12\n00:00:29.600 --> 00:00:34.600\nAnd what I really saw from that is it demystified business\n\n13\n00:00:34.600 --> 00:00:35.680\nand business leadership for me.\n\n14\n00:00:35.680 --> 00:00:38.280\nIt made me see that even the people at the top,\n\n15\n00:00:38.280 --> 00:00:40.600\nthe most admired and successful people in the world,\n\n16\n00:00:40.600 --> 00:00:41.680\nthey too have questions.\n\n17\n00:00:41.680 --> 00:00:42.760\nThere's things where they need help.\n\n18\n00:00:42.760 --> 00:00:43.960\nThere's things that they don't understand\n\n19\n00:00:43.960 --> 00:00:46.080\nor don't know how to do and could benefit\n\n20\n00:00:46.080 --> 00:00:48.120\neven from someone who could be out of college\n\n21\n00:00:48.120 --> 00:00:50.640\ncoming in and providing some information or perspective\n\n22\n00:00:50.640 --> 00:00:51.480\nthat they needed.\n\n23\n00:00:51.480 --> 00:00:54.760\nSo I think for me that really opened up this idea\n\n24\n00:00:54.760 --> 00:00:57.520\nthat like anyone can be successful in business,\n\n25\n00:00:57.520 --> 00:00:58.920\nwe can all have a shot at it\n\n26\n00:00:58.920 --> 00:01:01.120\nand there's nothing especially unique about people\n\n27\n00:01:01.120 --> 00:01:02.320\nwho are already very successful.\n\n28\n00:01:02.320 --> 00:01:05.280\nLike they got there through a hard lessons learned\n\n29\n00:01:05.280 --> 00:01:06.680\nbut also are still learning every day\n\n30\n00:01:06.680 --> 00:01:08.360\nand that that journey is never done.\n","pretty_transcript","start_time",486739,"end_time",555019,"keywords","Development, learning, continuous learning, mckinsey, consulting, opportunity","slug","even-top-leaders-are-still-figuring-stuff-out","origin","cms","mux_playback_id","HS2OZB99prjiojixQz5397M2nUL1QqfRLIQBoiYe00z8","mux_asset_id","yqfb3ZkYwRfs3Xt02ypnK8t2go9Uqzq01qL4Epwroqf7c","leader_id",244,"episode_id",396,"updated_at","2025-09-11T18:55:43.000000Z","meta_title","meta_description","og_image_media_id","web_url","https://www.howleaderslead.com/clips/3036/even-top-leaders-are-still-figuring-stuff-out","og_image_url","leader",{"_13":36,"_102":103,"_104":105,"_106":107,"_25":108,"_109":110,"_61":111,"_58":112,"_113":114,"_68":115,"_39":116,"_117":-5,"_41":-5,"_42":-5,"_43":-5,"_118":119,"_90":120,"_44":121,"_122":123,"_124":125,"_46":-5,"_126":127,"_128":129,"_94":130,"_51":-5},"episode",{"_13":38,"_15":52,"_27":53,"_17":54,"_55":56,"_18":57,"_20":-5,"_58":59,"_60":-5,"_61":59,"_62":-5,"_63":64,"_65":66,"_67":-5,"_68":-5,"_69":70,"_71":72,"_73":74,"_35":36,"_39":75,"_41":-5,"_42":-5,"_43":-5,"_76":77,"_78":79,"_80":81,"_82":83,"_84":-5,"_85":-5,"_86":87,"_88":89,"_90":-5,"_46":-5,"_91":92,"_93":-5,"_94":-5,"_51":-5},"og_image_media","Create clarity for your team","create-clarity-for-your-team","Listen to this leadership podcast with Hayden Brown, CEO of Upwork, and discover what it takes to give your team clarity.","summary","

Feeling stuck as a team, even though everyone’s working hard?

Hayden Brown, CEO of the global freelance marketplace Upwork, joins David Novak to reveal why CLARITY might be the missing ingredient in your leadership development.

In this episode of How Leaders Lead, Hayden shares how she guides her team through a rapidly changing world with clear vision, priorities, and communication.

She’s also on the front lines of building remote teams, hiring freelance talent, and developing AI capability – all huge topics every leader needs to stay sharp on.

YOU’LL ALSO LEARN:

Three practical strategies to build strong, healthy remote/hybrid teams
How to drive more AI adoption in your organization
One big shift you should be aware of before you make your next hire
What hard decisions really require from you

","WEBVTT\n\n1\n00:00:00.000 --> 00:00:05.360\nAs a leader, we have to start with a clear and shared narrative of what's the\n\n2\n00:00:05.360 --> 00:00:05.840\nmarket\n\n3\n00:00:05.840 --> 00:00:08.680\nand what's our situation in the market and what's the problem to be solved or\n\n4\n00:00:08.680 --> 00:00:09.680\nthe job to be done.\n\n5\n00:00:09.680 --> 00:00:12.590\nIf we don't know what problem we're solving or we don't know who we're solving\n\n6\n00:00:12.590 --> 00:00:12.880\nit for,\n\n7\n00:00:12.880 --> 00:00:15.500\nwe can do all these other steps and they will not move the needle on our\n\n8\n00:00:15.500 --> 00:00:16.320\nultimate goals.\n\n9\n00:00:16.320 --> 00:00:21.040\nIf you've ever felt like your team is working harder than ever, but not really\n\n10\n00:00:21.040 --> 00:00:22.080\ngetting anywhere,\n\n11\n00:00:22.080 --> 00:00:26.760\nit might not be an effort problem. It might be a clarity problem. Welcome to\n\n12\n00:00:26.760 --> 00:00:27.840\nHowl Leaders Lead.\n\n13\n00:00:27.840 --> 00:00:32.050\nI'm David Novak and every week I have conversations with the very best leaders\n\n14\n00:00:32.050 --> 00:00:33.040\nin the world to help\n\n15\n00:00:33.040 --> 00:00:38.440\nyou become the best leader you can be. My guest today is Hayden Brown, the CEO\n\n16\n00:00:38.440 --> 00:00:39.600\nof Upwork. Now,\n\n17\n00:00:39.600 --> 00:00:43.520\nif you aren't familiar with Upwork, they help companies find and hire top\n\n18\n00:00:43.520 --> 00:00:44.640\nfreelance talent.\n\n19\n00:00:44.640 --> 00:00:51.590\nAnd leading in that space, Hayden has real expertise on two topics every leader\n\n20\n00:00:51.590 --> 00:00:52.800\nis talking about right\n\n21\n00:00:52.800 --> 00:00:58.640\nnow, remote work and AI. You'll hear her insights on both and they're terrific,\n\n22\n00:00:58.640 --> 00:00:59.600\nbut I also want\n\n23\n00:00:59.600 --> 00:01:03.650\nyou to listen to Howl Hayden creates clarity for a team. If you want to cut\n\n24\n00:01:03.650 --> 00:01:04.880\ndown on confusion and\n\n25\n00:01:04.880 --> 00:01:09.330\ngive your team more direction and confidence, you're in the right place. Here's\n\n26\n00:01:09.330 --> 00:01:10.240\nmy conversation\n\n27\n00:01:10.240 --> 00:01:13.520\nwith my good friend and soon to be yours, Hayden Brown.\n\n28\n00:01:19.520 --> 00:01:24.070\nNow, I understand that you have actually learned a lot about how to run your\n\n29\n00:01:24.070 --> 00:01:25.680\nbusiness by studying\n\n30\n00:01:25.680 --> 00:01:32.800\ndating sites. Tell me about that. A big function of what we do at Upwork is\n\n31\n00:01:32.800 --> 00:01:34.400\nconnecting businesses\n\n32\n00:01:34.400 --> 00:01:39.570\nfrom the Fortune 100, companies like Microsoft, Airbnb, CloudFlare, all the way\n\n33\n00:01:39.570 --> 00:01:40.400\ndown to your local\n\n34\n00:01:40.400 --> 00:01:44.470\nmom and pop company. We connect them with the most in-demand talent in the\n\n35\n00:01:44.470 --> 00:01:46.240\nworld. And of course,\n\n36\n00:01:46.240 --> 00:01:50.080\nthat's a large part of matchmaking. That's really where we're finding the exact\n\n37\n00:01:50.080 --> 00:01:50.960\nmatch for not just\n\n38\n00:01:50.960 --> 00:01:54.880\nthe company, but the hiring manager, the project, the specific issue that they\n\n39\n00:01:54.880 --> 00:01:56.080\n're trying to solve,\n\n40\n00:01:56.080 --> 00:01:59.920\nand going into our tremendous talent pool to find that person. So there are a\n\n41\n00:01:59.920 --> 00:02:01.200\nlot of analogies to\n\n42\n00:02:01.200 --> 00:02:04.840\ndating sites and matchmaking services generally. And certainly, we always try\n\n43\n00:02:04.840 --> 00:02:05.280\nto pull from the\n\n44\n00:02:05.280 --> 00:02:08.270\nbest to figure out how we do that matching better and better every day for our\n\n45\n00:02:08.270 --> 00:02:08.960\ncustomers.\n\n46\n00:02:08.960 --> 00:02:12.800\nWhat do you think has been the biggest insight you pulled from the dating sites\n\n47\n00:02:12.800 --> 00:02:13.120\nthat you've\n\n48\n00:02:13.120 --> 00:02:17.440\ntransferred over? I think one thing that makes dating sites an interesting\n\n49\n00:02:17.440 --> 00:02:18.720\nanalogy for us is\n\n50\n00:02:18.720 --> 00:02:25.920\nunlike e-commerce where someone can come into a website and browse a bunch of\n\n51\n00:02:25.920 --> 00:02:26.240\nproducts,\n\n52\n00:02:26.240 --> 00:02:29.760\nand then many people could order that same product. They have thousands of that\n\n53\n00:02:29.760 --> 00:02:30.080\nproduct on\n\n54\n00:02:30.080 --> 00:02:34.800\ninventory. In the world of dating sites and the world of Upwork, every person\n\n55\n00:02:34.800 --> 00:02:35.680\nis unique.\n\n56\n00:02:35.680 --> 00:02:39.690\nThere's no two people are the same. There's no two orders you could make of the\n\n57\n00:02:39.690 --> 00:02:40.320\nsame thing\n\n58\n00:02:40.320 --> 00:02:44.850\nthrough our platform. And so we really look at how dating sites kind of bring\n\n59\n00:02:44.850 --> 00:02:46.240\nforward the uniqueness,\n\n60\n00:02:46.240 --> 00:02:50.510\nthe specialness of every person, and find those very specific attributes that\n\n61\n00:02:50.510 --> 00:02:51.040\nbecome part of the\n\n62\n00:02:51.040 --> 00:02:55.940\nmatching algorithm to get the right person to that individual. Tell me about\n\n63\n00:02:55.940 --> 00:02:57.200\nthe origin of Upwork\n\n64\n00:02:57.200 --> 00:03:04.690\nand what it is today. We were founded about 20 years ago really through two\n\n65\n00:03:04.690 --> 00:03:05.280\nvery good childhood\n\n66\n00:03:05.280 --> 00:03:09.690\nfriends who grew up in Greece. And one of them moved to the US and he really\n\n67\n00:03:09.690 --> 00:03:10.640\nwanted to work with\n\n68\n00:03:10.640 --> 00:03:14.960\nhis good old friend from Greece who was still back in that country. And yet he\n\n69\n00:03:14.960 --> 00:03:15.760\nfound in the early\n\n70\n00:03:15.760 --> 00:03:20.410\n2000s, it was not easy to do this. And in fact, his employer was pushing back\n\n71\n00:03:20.410 --> 00:03:21.280\nand saying, \"Well,\n\n72\n00:03:21.280 --> 00:03:23.990\nwe don't know this person and how do we trust them and how do we know they're\n\n73\n00:03:23.990 --> 00:03:25.520\ndoing real work for us.\"\n\n74\n00:03:25.520 --> 00:03:30.260\nAnd that really led him and his friend to start Odesk, which was basically a\n\n75\n00:03:30.260 --> 00:03:31.440\nway to connect\n\n76\n00:03:31.440 --> 00:03:35.310\nremote talent together with a trusted paradigm where there were things like\n\n77\n00:03:35.310 --> 00:03:36.560\nscreen captures,\n\n78\n00:03:36.560 --> 00:03:40.640\nhourly work guarantees on both sides, and all the infrastructure to make remote\n\n79\n00:03:40.640 --> 00:03:42.000\nwork safe, secure,\n\n80\n00:03:42.000 --> 00:03:45.760\nand appetizing for both businesses and talent. So that was the early story of\n\n81\n00:03:45.760 --> 00:03:46.640\nour business.\n\n82\n00:03:46.640 --> 00:03:50.640\nWe've gone through a ton of chapters since then, birds with our arch rival,\n\n83\n00:03:50.640 --> 00:03:55.120\nElance, and become Upwork in 2015. But really, this is a business that I think\n\n84\n00:03:55.120 --> 00:03:55.840\nat the beginning\n\n85\n00:03:55.840 --> 00:03:59.070\nof the next huge journey. And I'm sure we'll talk about that, but AI is\n\n86\n00:03:59.070 --> 00:04:00.480\nchanging everything to do\n\n87\n00:04:00.480 --> 00:04:04.480\nwith work. And we're certainly at the forefront of that with our product and\n\n88\n00:04:04.480 --> 00:04:05.440\nfor our customers.\n\n89\n00:04:05.440 --> 00:04:08.800\nWell, there probably isn't a company in the world that knows more about remote\n\n90\n00:04:08.800 --> 00:04:09.520\nworking and\n\n91\n00:04:09.520 --> 00:04:12.520\nhow to make it work than you. And I can't wait to really get into that as we go\n\n92\n00:04:12.520 --> 00:04:13.120\nthrough along.\n\n93\n00:04:13.120 --> 00:04:16.010\nBut I'm going to ask you lots of questions about how you're leading Upwork, but\n\n94\n00:04:16.010 --> 00:04:16.480\nI'm going to take\n\n95\n00:04:16.480 --> 00:04:20.840\nyou back. And what's the story from your childhood that shaped the kind of\n\n96\n00:04:20.840 --> 00:04:21.920\nleader you are today?\n\n97\n00:04:21.920 --> 00:04:27.090\nYou know, I've been an entrepreneur since I was a really little kid. And the\n\n98\n00:04:27.090 --> 00:04:28.960\nstory there was,\n\n99\n00:04:28.960 --> 00:04:32.930\nI grew up in the small town in Massachusetts of blue collar community. Everyone\n\n100\n00:04:32.930 --> 00:04:34.000\nknew everyone.\n\n101\n00:04:34.000 --> 00:04:37.920\nAnd when I was six years old, my older brother was paralyzed from the neck down\n\n102\n00:04:37.920 --> 00:04:39.040\nvery suddenly.\n\n103\n00:04:39.040 --> 00:04:42.680\nHe's fine today, but he got this rare autoimmune disease called Guillaume Barre\n\n104\n00:04:42.680 --> 00:04:43.760\nsyndrome and suddenly\n\n105\n00:04:43.760 --> 00:04:47.520\nwas in the hospital for six months. And there I was, this little kid loving and\n\n106\n00:04:47.520 --> 00:04:48.160\nidolizing my\n\n107\n00:04:48.160 --> 00:04:51.400\nbrother and trying to figure out, what can I do for him? How can I make his\n\n108\n00:04:51.400 --> 00:04:52.400\nlife better when he's\n\n109\n00:04:52.400 --> 00:04:57.540\nin this situation? And I got this idea because he was a huge car nut that when\n\n110\n00:04:57.540 --> 00:04:58.560\nhe got out of the\n\n111\n00:04:58.560 --> 00:05:02.250\nhospital, I wanted him to come home in a stretch limousine. Like this was the\n\n112\n00:05:02.250 --> 00:05:02.960\nthing I wanted to\n\n113\n00:05:02.960 --> 00:05:06.820\ndo with his friends inside this big surprise, this big moment. And yet my\n\n114\n00:05:06.820 --> 00:05:07.920\nallowance wasn't going\n\n115\n00:05:07.920 --> 00:05:12.280\nto cover that. Like I had no way to fund that type of car rental. So I got\n\n116\n00:05:12.280 --> 00:05:13.360\nstarted collecting\n\n117\n00:05:13.360 --> 00:05:17.200\nbottles and cans, turning them into the recycling center, getting five cents\n\n118\n00:05:17.200 --> 00:05:18.480\neach. And thousands of\n\n119\n00:05:18.480 --> 00:05:23.570\ncans later, I had enough money to pay for the surprise limo trip for him home.\n\n120\n00:05:23.570 --> 00:05:24.160\nBut what I really\n\n121\n00:05:24.160 --> 00:05:28.970\ngot from that wasn't just like the joy of seeing him in that experience. I\n\n122\n00:05:28.970 --> 00:05:30.320\nrealized how powerful it\n\n123\n00:05:30.320 --> 00:05:33.200\nwas to have earned money as like a little kid to be able to actually do\n\n124\n00:05:33.200 --> 00:05:34.240\nsomething with it that\n\n125\n00:05:34.240 --> 00:05:37.980\nreally made someone else's life better. And that led me to go on and get a\n\n126\n00:05:37.980 --> 00:05:39.040\npaper route. I was\n\n127\n00:05:39.040 --> 00:05:41.990\nprobably the youngest in my town to do that to start a small business called\n\n128\n00:05:41.990 --> 00:05:43.440\nHayden's house cleaning.\n\n129\n00:05:43.440 --> 00:05:46.800\nI went around the neighborhood doing chores for people. I went on sort of the\n\n130\n00:05:46.800 --> 00:05:47.360\nsummer camp for\n\n131\n00:05:47.360 --> 00:05:51.360\nlocal kids like all of these things were important to me. But the through line\n\n132\n00:05:51.360 --> 00:05:53.360\nwas that early experience\n\n133\n00:05:53.360 --> 00:05:57.480\nwhere I saw the good that I could do as an entrepreneur and seeing my parents\n\n134\n00:05:57.480 --> 00:05:58.080\nwho were\n\n135\n00:05:58.080 --> 00:06:01.700\nnonprofit people and we're working in communities around the world. We moved to\n\n136\n00:06:01.700 --> 00:06:02.960\nNepal when I was 11,\n\n137\n00:06:02.960 --> 00:06:07.040\nwe lived in Kathmandu and they taught me the importance of not just doing work\n\n138\n00:06:07.040 --> 00:06:07.600\nbut doing work\n\n139\n00:06:07.600 --> 00:06:11.520\nwith a purpose, doing work that really has a positive impact on people's lives,\n\n140\n00:06:11.520 --> 00:06:11.920\nwhich is what\n\n141\n00:06:11.920 --> 00:06:16.570\nthey dedicated their lives to. And so that whole experience led me to want to\n\n142\n00:06:16.570 --> 00:06:17.840\nbe in business and\n\n143\n00:06:17.840 --> 00:06:21.620\ncreate new things, create new products, but do it in a way that really tied\n\n144\n00:06:21.620 --> 00:06:23.200\nback to personal impact\n\n145\n00:06:23.200 --> 00:06:26.800\nhuman impact. And that's really one of the big reasons I'm at Upwork today.\n\n146\n00:06:26.800 --> 00:06:33.630\nYeah, that's fantastic story. And you lived in Nepal. What was the biggest\n\n147\n00:06:33.630 --> 00:06:34.640\nthing you took out\n\n148\n00:06:34.640 --> 00:06:39.830\nof that experience? You know, about a year after we had moved to Nepal, I\n\n149\n00:06:39.830 --> 00:06:41.200\nremember my first trip\n\n150\n00:06:41.200 --> 00:06:45.530\nback to the US. So I was 12 years old. I got off the airplane within a few\n\n151\n00:06:45.530 --> 00:06:46.960\nhours. I found myself\n\n152\n00:06:46.960 --> 00:06:52.060\nin a US supermarket, probably a stop and shop in Massachusetts. And I'll never\n\n153\n00:06:52.060 --> 00:06:52.720\nforget\n\n154\n00:06:53.040 --> 00:06:57.820\nthe kind of wonder that I had walking down the aisles and seeing 12 brands of\n\n155\n00:06:57.820 --> 00:06:58.880\ntoothpaste,\n\n156\n00:06:58.880 --> 00:07:03.140\nyou know, 55 serial types, like all of this abundance that previously I had\n\n157\n00:07:03.140 --> 00:07:04.000\njust taken for\n\n158\n00:07:04.000 --> 00:07:07.770\ngranted growing up in the US. But now having been overseas for a while and\n\n159\n00:07:07.770 --> 00:07:08.800\nseeing obviously\n\n160\n00:07:08.800 --> 00:07:13.490\nsuch a different level of access and opportunity in Kathmandu, I realized as\n\n161\n00:07:13.490 --> 00:07:14.720\nAmericans, we are\n\n162\n00:07:14.720 --> 00:07:17.920\nso privileged and we have so much access and things that we just take for\n\n163\n00:07:17.920 --> 00:07:19.120\ngranted, the rest of the\n\n164\n00:07:19.120 --> 00:07:24.290\nworld would literally move night and day and like do anything to access. So\n\n165\n00:07:24.290 --> 00:07:25.120\nthat was a huge wake-up\n\n166\n00:07:25.120 --> 00:07:29.100\ncall for me really seeing that disparity and understanding firsthand the\n\n167\n00:07:29.100 --> 00:07:30.080\nprivilege of being an\n\n168\n00:07:30.080 --> 00:07:33.040\nAmerican. It felt like I was born with a lottery ticket because of that and\n\n169\n00:07:33.040 --> 00:07:34.000\nstarting to figure out\n\n170\n00:07:34.000 --> 00:07:37.310\nhow can I help others in the world have access to this incredible opportunity\n\n171\n00:07:37.310 --> 00:07:38.240\nthat we have here in\n\n172\n00:07:38.240 --> 00:07:42.570\nthe US. That's so great. You know, people always ask me what my biggest break\n\n173\n00:07:42.570 --> 00:07:43.360\nis. And I always tell\n\n174\n00:07:43.360 --> 00:07:47.050\nthem that being born in the United States of America and the son of Charles and\n\n175\n00:07:47.050 --> 00:07:47.680\nGene Novak,\n\n176\n00:07:47.680 --> 00:07:53.760\nsounds like you have the same kind of belief that I have on that. And you know,\n\n177\n00:07:53.760 --> 00:07:55.840\nyou go to Princeton\n\n178\n00:07:55.840 --> 00:08:00.260\nand you graduate there, grade school, and then you start up your career at\n\n179\n00:08:00.260 --> 00:08:02.240\nMcKinsey. You know,\n\n180\n00:08:02.240 --> 00:08:07.320\nwhen you think about leadership and making an impact, what did you learn by\n\n181\n00:08:07.320 --> 00:08:08.560\nbeing a consultant?\n\n182\n00:08:08.560 --> 00:08:13.280\nYou know, I'll share this lesson with you. I don't know how appealing will be\n\n183\n00:08:13.280 --> 00:08:14.640\nto people, but actually\n\n184\n00:08:14.640 --> 00:08:20.880\nit was such an incredible experience to be 21, 22 years old and asked to go in\n\n185\n00:08:20.880 --> 00:08:21.360\nand work with some\n\n186\n00:08:21.360 --> 00:08:24.830\nof the biggest companies in the world on core strategic problems that they were\n\n187\n00:08:24.830 --> 00:08:26.000\nstruggling with,\n\n188\n00:08:26.000 --> 00:08:29.690\nthat they did not have answers to. And that was exactly why they were, we were\n\n189\n00:08:29.690 --> 00:08:30.400\nthere as a firm\n\n190\n00:08:30.400 --> 00:08:34.310\nand why I was being asked to do analysis or research or prepare a presentation\n\n191\n00:08:34.310 --> 00:08:35.520\nthat summarized\n\n192\n00:08:35.520 --> 00:08:41.330\nvarious things. And what I really saw from that is it demystified business and\n\n193\n00:08:41.330 --> 00:08:42.080\nbusiness leadership\n\n194\n00:08:42.080 --> 00:08:45.760\nfor me, it made me see that even the people at the top, the most admired and\n\n195\n00:08:45.760 --> 00:08:46.800\nsuccessful people in the\n\n196\n00:08:46.800 --> 00:08:49.410\nworld, they too have questions. There's things where they need help. There's\n\n197\n00:08:49.410 --> 00:08:50.080\nthings that they don't\n\n198\n00:08:50.080 --> 00:08:53.780\nunderstand or don't know how to do and could benefit even from someone who's\n\n199\n00:08:53.780 --> 00:08:54.880\nsure out of the college\n\n200\n00:08:54.880 --> 00:08:58.460\ncoming in and providing some information or perspective that they needed. So I\n\n201\n00:08:58.460 --> 00:09:00.320\nthink for me that really\n\n202\n00:09:00.320 --> 00:09:04.720\nopened up this idea that like anyone can be successful in business, we can all\n\n203\n00:09:04.720 --> 00:09:05.680\nhave a shot at it. And\n\n204\n00:09:05.680 --> 00:09:09.040\nthere's nothing especially unique about people who are already very successful.\n\n205\n00:09:09.040 --> 00:09:09.920\nLike they got there\n\n206\n00:09:09.920 --> 00:09:13.680\nthrough a hard lessons learned, but also are still learning every day and that\n\n207\n00:09:13.680 --> 00:09:14.640\nthat journey is never\n\n208\n00:09:14.640 --> 00:09:20.960\ndone. And you were this huge company Microsoft for a while. What did you glean\n\n209\n00:09:20.960 --> 00:09:22.720\nfrom that experience\n\n210\n00:09:22.720 --> 00:09:28.730\nthat you've taken with you to upwork? Culture is everything. I was at Microsoft\n\n211\n00:09:28.730 --> 00:09:29.360\nat a time\n\n212\n00:09:29.360 --> 00:09:33.700\nwhen there was that famous cartoon of the different divisions pointing guns at\n\n213\n00:09:33.700 --> 00:09:34.560\neach other because it\n\n214\n00:09:34.560 --> 00:09:39.000\nwas very fraught internally and there was a lot of internal competition. And\n\n215\n00:09:39.000 --> 00:09:40.240\nyet I was privileged\n\n216\n00:09:40.240 --> 00:09:44.890\nenough to join a team that was nothing like that. We had this small team that\n\n217\n00:09:44.890 --> 00:09:46.720\nwas this ninja force\n\n218\n00:09:46.720 --> 00:09:51.310\nfirst working on M&A and strategy for the online business, which was this new\n\n219\n00:09:51.310 --> 00:09:52.720\nthing at the time,\n\n220\n00:09:52.720 --> 00:09:55.720\nand then going on and working on the biggest corporate strategy deals in the\n\n221\n00:09:55.720 --> 00:09:56.480\ncompany's history,\n\n222\n00:09:56.480 --> 00:10:01.290\nincluding things like the $40+ billion acquisition bid on Yahoo, the investment\n\n223\n00:10:01.290 --> 00:10:02.480\nin Facebook, etc.\n\n224\n00:10:02.480 --> 00:10:06.880\nAnd I saw that the culture of our team, which was so different than the broader\n\n225\n00:10:06.880 --> 00:10:07.280\nculture of\n\n226\n00:10:07.280 --> 00:10:10.750\nMicrosoft, was really a huge motivator for me and a reason I stayed and did\n\n227\n00:10:10.750 --> 00:10:11.920\nthat work and just loved\n\n228\n00:10:11.920 --> 00:10:15.440\nit and grew so much. Whereas once I realized I wanted to go into product\n\n229\n00:10:15.440 --> 00:10:16.400\nmanagement and do\n\n230\n00:10:16.400 --> 00:10:20.020\nsomething else with my career, I knew going into the rest of Microsoft at that\n\n231\n00:10:20.020 --> 00:10:21.120\ntime in that culture\n\n232\n00:10:21.120 --> 00:10:24.160\nwas just not appealing at all. And so I've carried that with me and thinking\n\n233\n00:10:24.160 --> 00:10:25.200\nabout how do I build\n\n234\n00:10:25.200 --> 00:10:29.100\nit upwork? The right culture that really attracts and retains, I guess, the\n\n235\n00:10:29.100 --> 00:10:30.080\nbest out of people and\n\n236\n00:10:30.080 --> 00:10:34.330\nis not political, is not discordant internally, but really has us all moving in\n\n237\n00:10:34.330 --> 00:10:35.600\nthe same direction.\n\n238\n00:10:35.600 --> 00:10:39.100\nAnd when you think about culture at Upwork, what do you think is the single\n\n239\n00:10:39.100 --> 00:10:39.920\nmost important\n\n240\n00:10:39.920 --> 00:10:43.840\nbehavior that you're really trying to drive that will get results?\n\n241\n00:10:43.840 --> 00:10:49.600\nWe have a value called build and break fearlessly. And we have a number of\n\n242\n00:10:49.600 --> 00:10:50.960\ncompany values. We have\n\n243\n00:10:50.960 --> 00:10:55.600\nfive total values, but this one is the one that I think really animates our\n\n244\n00:10:55.600 --> 00:10:56.640\nculture and our reason\n\n245\n00:10:56.640 --> 00:11:01.980\nof being the most because we're a company that's built to break the status quo,\n\n246\n00:11:01.980 --> 00:11:03.200\nto create possibilities\n\n247\n00:11:03.200 --> 00:11:06.740\nfor people and businesses that did not exist before and would not exist without\n\n248\n00:11:06.740 --> 00:11:07.520\nour platform.\n\n249\n00:11:07.520 --> 00:11:12.560\nSo we need to be fearless every day, examining what needs to change, not just\n\n250\n00:11:12.560 --> 00:11:13.360\nin the ecosystem\n\n251\n00:11:13.360 --> 00:11:17.550\noutside and where we're trying to influence stakeholders, customers, etc. But\n\n252\n00:11:17.550 --> 00:11:18.320\nhow do we need\n\n253\n00:11:18.320 --> 00:11:22.350\nto build and break our own culture or our own ways of working or our own\n\n254\n00:11:22.350 --> 00:11:23.360\npractices to actually\n\n255\n00:11:23.360 --> 00:11:27.760\nachieve these goals for our customers? So this value for us cuts very deep and\n\n256\n00:11:27.760 --> 00:11:28.720\nshows up in all\n\n257\n00:11:28.720 --> 00:11:32.290\naspects of our work. And as they think, the thing that keeps us innovating at\n\n258\n00:11:32.290 --> 00:11:33.280\nthe edge of\n\n259\n00:11:33.280 --> 00:11:36.960\nkind of the comfort zone and kind of pioneering our space in a way we cannot do\n\n260\n00:11:36.960 --> 00:11:37.680\nif we weren't so\n\n261\n00:11:37.680 --> 00:11:41.470\nanchored on this value. When you're talking to your team about the importance\n\n262\n00:11:41.470 --> 00:11:42.240\nof break and build,\n\n263\n00:11:42.240 --> 00:11:47.440\nwhat's what's your favorite story you tell? There's so many. I mean, we just\n\n264\n00:11:47.440 --> 00:11:48.160\nhad a huge\n\n265\n00:11:48.160 --> 00:11:52.650\nannouncement on Tuesday, which was around this new business unit and a brand we\n\n266\n00:11:52.650 --> 00:11:53.280\nlaunched\n\n267\n00:11:53.280 --> 00:11:58.660\ncalled Lifted. And we created this business through two acquisitions plus our\n\n268\n00:11:58.660 --> 00:11:59.840\nown existing\n\n269\n00:11:59.840 --> 00:12:04.010\nenterprise business put together in this new structure. And I will say this is\n\n270\n00:12:04.010 --> 00:12:04.400\nprobably the\n\n271\n00:12:04.400 --> 00:12:08.150\nbiggest build and break fearlessly moment that we've had because this required\n\n272\n00:12:08.150 --> 00:12:08.960\nus not just to\n\n273\n00:12:08.960 --> 00:12:14.380\ndo acquisitions or change our product or change our sales strategy. It actually\n\n274\n00:12:14.380 --> 00:12:14.960\ncaused us to\n\n275\n00:12:14.960 --> 00:12:21.360\nrestructure our business and create this unit and kind of completely change our\n\n276\n00:12:21.360 --> 00:12:22.240\noperating model in\n\n277\n00:12:22.240 --> 00:12:25.150\norder to be able to serve our customers the way we knew they needed to be\n\n278\n00:12:25.150 --> 00:12:26.320\nserved. And so this one,\n\n279\n00:12:26.320 --> 00:12:29.910\nI think, is a great example of how we went deep inside and not just outside in\n\n280\n00:12:29.910 --> 00:12:30.720\nterms of how we\n\n281\n00:12:30.720 --> 00:12:34.850\napply this value and really did the hard work to set us up for this next great\n\n282\n00:12:34.850 --> 00:12:35.600\nchapter.\n\n283\n00:12:35.600 --> 00:12:40.640\nAnd as I understand it, when you joined Upwork, you were the head of product.\n\n284\n00:12:40.640 --> 00:12:42.800\nWhat does\n\n285\n00:12:42.800 --> 00:12:46.960\nhead of product mean in a company like Upwork? What'd you do?\n\n286\n00:12:47.600 --> 00:12:51.440\nYeah, so I joined the company in 2011, actually as a product manager, I found\n\n287\n00:12:51.440 --> 00:12:52.800\nthe head of product\n\n288\n00:12:52.800 --> 00:12:57.090\nat the time was willing to take that bet on me transitioning from strategy and\n\n289\n00:12:57.090 --> 00:12:57.760\nM&A and this other\n\n290\n00:12:57.760 --> 00:13:01.660\npart of my career into actually being a builder. And then I grew up to be the\n\n291\n00:13:01.660 --> 00:13:02.560\nhead of product and\n\n292\n00:13:02.560 --> 00:13:06.820\nthen brand marketing before becoming CEO five and a half years ago. But what I\n\n293\n00:13:06.820 --> 00:13:07.840\nsaw with being a\n\n294\n00:13:07.840 --> 00:13:12.060\nproduct was this was such an amazing through line between really understanding\n\n295\n00:13:12.060 --> 00:13:12.960\ncustomer needs\n\n296\n00:13:12.960 --> 00:13:17.440\nvery deeply. And then being analytical and focused about how to action those\n\n297\n00:13:17.440 --> 00:13:18.160\nneeds and also being\n\n298\n00:13:18.160 --> 00:13:22.570\nvery creative in terms of solutioning design, product development. And then of\n\n299\n00:13:22.570 --> 00:13:24.240\ncourse, closing\n\n300\n00:13:24.240 --> 00:13:27.940\nthat feedback loop by seeing what happens when you ship those products, how\n\n301\n00:13:27.940 --> 00:13:29.040\ncustomers engage with\n\n302\n00:13:29.040 --> 00:13:31.670\nit, how they respond, and then using that of course to come back to the\n\n303\n00:13:31.670 --> 00:13:32.720\nbeginning of the process\n\n304\n00:13:32.720 --> 00:13:37.360\nall over again. So I loved how I got to be so front and center with customers,\n\n305\n00:13:37.360 --> 00:13:37.760\nunderstanding\n\n306\n00:13:37.760 --> 00:13:41.060\ntheir problems and then applying them directly into changes in our business to\n\n307\n00:13:41.060 --> 00:13:41.680\naddress those\n\n308\n00:13:41.680 --> 00:13:45.970\nproblems. You know, one of the things that I think is the case, and you can\n\n309\n00:13:45.970 --> 00:13:46.880\ncorrect me if I'm wrong,\n\n310\n00:13:46.880 --> 00:13:52.710\nbut you have a big perception of being this company that hires freelancers for\n\n311\n00:13:52.710 --> 00:13:53.680\ncreative projects,\n\n312\n00:13:53.680 --> 00:14:00.680\nbut yet you've expanded over time to human resources, IT, finance, how\n\n313\n00:14:00.680 --> 00:14:02.880\nchallenging was that for you to\n\n314\n00:14:02.880 --> 00:14:09.200\ntake people with you to broaden your offerings? This happened really naturally\n\n315\n00:14:09.200 --> 00:14:10.240\nfor our platform\n\n316\n00:14:10.240 --> 00:14:15.600\nactually. We started with a really strong foothold in technical work. So we had\n\n317\n00:14:15.600 --> 00:14:16.240\na lot of Eastern\n\n318\n00:14:16.240 --> 00:14:20.470\nEuropean talent and others around the world doing web and mobile software and\n\n319\n00:14:20.470 --> 00:14:21.760\napplication design,\n\n320\n00:14:21.760 --> 00:14:25.360\nall of that work kind of in the early 2000s. And then you're right, we also had\n\n321\n00:14:25.360 --> 00:14:25.760\nthis very\n\n322\n00:14:25.760 --> 00:14:29.820\nstrong hold, big strong hold with designing creative work. But what we saw is\n\n323\n00:14:29.820 --> 00:14:31.040\ncustomers would come in,\n\n324\n00:14:31.040 --> 00:14:34.560\nyou know, they'd have something in mind like build a website, but that was not\n\n325\n00:14:34.560 --> 00:14:35.760\nsomething that just\n\n326\n00:14:35.760 --> 00:14:38.960\na designer or a developer could do in isolation. They needed design,\n\n327\n00:14:38.960 --> 00:14:40.480\ndevelopment, marketing, you\n\n328\n00:14:40.480 --> 00:14:44.690\nknow, they needed the full spectrum of skills to execute these bigger projects.\n\n329\n00:14:44.690 --> 00:14:46.000\nSo very naturally,\n\n330\n00:14:46.000 --> 00:14:49.540\nthey started looking for and finding talent on our platform that drove that fly\n\n331\n00:14:49.540 --> 00:14:50.160\nwheel where now we\n\n332\n00:14:50.160 --> 00:14:54.880\nhave over 130 categories of work, 250,000 AI specialists globally. I mean, and\n\n333\n00:14:54.880 --> 00:14:55.680\nthe composition\n\n334\n00:14:55.680 --> 00:14:59.730\nof our marketplace continues to shape shift based on client demands, which is\n\n335\n00:14:59.730 --> 00:15:00.960\nlike an amazing aspect\n\n336\n00:15:00.960 --> 00:15:05.070\nof our marketplace. And you know, here you are now you're the leader in the\n\n337\n00:15:05.070 --> 00:15:06.400\nindustry, but you have\n\n338\n00:15:06.400 --> 00:15:12.510\ncompanies like Fiverr and others who trying to do the exact same thing or even\n\n339\n00:15:12.510 --> 00:15:13.600\nbetter, you know,\n\n340\n00:15:13.600 --> 00:15:19.120\nhow do you think about competition? You know, we stay focused on solving our\n\n341\n00:15:19.120 --> 00:15:19.920\nown customers'\n\n342\n00:15:19.920 --> 00:15:23.560\nproblems. And of course, we look at what others in the marketplace and the\n\n343\n00:15:23.560 --> 00:15:24.960\necosystem are doing.\n\n344\n00:15:24.960 --> 00:15:29.360\nBut we have such a unique solution that actually no one has replicated. There's\n\n345\n00:15:29.360 --> 00:15:30.000\nno one that does\n\n346\n00:15:30.000 --> 00:15:34.500\nwhat we do. You know, our we do complex large project work. We have deep\n\n347\n00:15:34.500 --> 00:15:35.280\nrelationships being\n\n348\n00:15:35.280 --> 00:15:39.290\nfostered between clients and talent on our marketplace. This is not small\n\n349\n00:15:39.290 --> 00:15:40.640\ntransactional stuff or throw\n\n350\n00:15:40.640 --> 00:15:44.790\nit over the wall to somebody talented. So, you know, our distinct value\n\n351\n00:15:44.790 --> 00:15:45.840\nproposition and kind of\n\n352\n00:15:45.840 --> 00:15:48.610\nmarket positioning is something that we see as a huge asset that we can\n\n353\n00:15:48.610 --> 00:15:50.000\ncontinue to expand on with\n\n354\n00:15:50.000 --> 00:15:53.150\nthings like our AI features and what we're doing there with things like this\n\n355\n00:15:53.150 --> 00:15:54.560\nenterprise expansion,\n\n356\n00:15:54.560 --> 00:15:58.970\nwhat we're doing there. And we see ourselves bring to the market solutions that\n\n357\n00:15:58.970 --> 00:15:59.760\nno one else has and\n\n358\n00:15:59.760 --> 00:16:03.310\nfrankly are really disrupting some of the legacy players who've been around for\n\n359\n00:16:03.310 --> 00:16:03.840\na long time but\n\n360\n00:16:03.840 --> 00:16:07.040\naren't tech enabled, don't have marketplaces, you know, don't have the set of\n\n361\n00:16:07.040 --> 00:16:07.840\ntalent and other\n\n362\n00:16:07.840 --> 00:16:12.500\ncapabilities that we have. Yeah. And you know, so how do you how do you stay in\n\n363\n00:16:12.500 --> 00:16:13.280\ntouch with the\n\n364\n00:16:13.280 --> 00:16:18.610\nvoice of the customer and and balance giving them what they're telling you they\n\n365\n00:16:18.610 --> 00:16:19.520\nneed versus\n\n366\n00:16:19.520 --> 00:16:23.040\nversus giving them sometimes things that they don't even know that they need?\n\n367\n00:16:23.040 --> 00:16:28.080\nIt's a great question. I mean, we talk to customers every single day. I mean,\n\n368\n00:16:28.080 --> 00:16:29.040\nwe're on the phone,\n\n369\n00:16:29.040 --> 00:16:34.720\non Zoom, you know, in person, I do an AI customer council every month where I\n\n370\n00:16:34.720 --> 00:16:35.600\ngather customers who\n\n371\n00:16:35.600 --> 00:16:39.610\nare focused on AI and are using our platform for AI and talk to them about what\n\n372\n00:16:39.610 --> 00:16:40.800\n's current and on\n\n373\n00:16:40.800 --> 00:16:45.200\ntheir minds. So, we have a ton of these channels for getting that feedback. But\n\n374\n00:16:45.200 --> 00:16:45.920\nyou're right, David.\n\n375\n00:16:45.920 --> 00:16:49.500\nYou know, one of the things I think is critical about a product manager and\n\n376\n00:16:49.500 --> 00:16:51.200\nabout a product company\n\n377\n00:16:51.200 --> 00:16:54.420\nis we can't just build what we're asked to build. We have to go beyond that and\n\n378\n00:16:54.420 --> 00:16:55.680\nhave a bigger vision\n\n379\n00:16:55.680 --> 00:16:58.760\nfor where we're headed that customers may not even, you know, fully grapple\n\n380\n00:16:58.760 --> 00:16:59.600\nwith yet. They might not\n\n381\n00:16:59.600 --> 00:17:02.950\nnot even be there yet, but we've got to be building that vision and making it\n\n382\n00:17:02.950 --> 00:17:04.560\nreal for them. So,\n\n383\n00:17:04.560 --> 00:17:08.330\nwe also do a lot internally in terms of putting stakes in the ground around how\n\n384\n00:17:08.330 --> 00:17:09.120\nwe see the market\n\n385\n00:17:09.120 --> 00:17:12.950\nevolving in the next few years where things like AI will transform our\n\n386\n00:17:12.950 --> 00:17:14.400\nopportunity, visioning that\n\n387\n00:17:14.400 --> 00:17:18.080\nout and then building a roadmap that is giving incremental wins to customers\n\n388\n00:17:18.080 --> 00:17:18.960\nalong the way. So,\n\n389\n00:17:18.960 --> 00:17:22.500\nthey're seeing those benefits. We're not waiting until that big reveal, but we\n\n390\n00:17:22.500 --> 00:17:23.360\n're building towards\n\n391\n00:17:23.360 --> 00:17:26.170\nsomething that once we get there, everyone will look back and go, this is\n\n392\n00:17:26.170 --> 00:17:26.800\ntotally different.\n\n393\n00:17:26.800 --> 00:17:30.480\nThis is totally transformational. Yeah, I want to get into how you're leading\n\n394\n00:17:30.480 --> 00:17:31.520\nin the world of AI,\n\n395\n00:17:31.520 --> 00:17:35.790\nbecause there are very few people doing it as well as you guys are doing it.\n\n396\n00:17:35.790 --> 00:17:37.680\nAnd, but you spent\n\n397\n00:17:37.680 --> 00:17:43.850\nalmost 10 years at Upwork before becoming the CEO. You know, not many rise to\n\n398\n00:17:43.850 --> 00:17:44.800\nthat position of\n\n399\n00:17:44.800 --> 00:17:49.580\nCEO being at the top of the organization. If you had to pick one thing that\n\n400\n00:17:49.580 --> 00:17:51.600\nreally was the key driver\n\n401\n00:17:51.600 --> 00:17:55.680\nof your own personal success as a leader, what do you think it would be?\n\n402\n00:17:55.680 --> 00:18:01.330\nI think clarity is probably the most important thing if I look back. And at\n\n403\n00:18:01.330 --> 00:18:03.120\nevery step of the way,\n\n404\n00:18:03.120 --> 00:18:07.920\nI really focused on bringing clarity to hard problems that we didn't know how\n\n405\n00:18:07.920 --> 00:18:08.800\nto solve or,\n\n406\n00:18:08.800 --> 00:18:13.760\nor, you know, hadn't resolved yet. Also bringing clarity to what's the actual\n\n407\n00:18:13.760 --> 00:18:14.640\nsituation in the\n\n408\n00:18:14.640 --> 00:18:18.510\nbusiness? Because as a leader, we have to start with a clear and shared\n\n409\n00:18:18.510 --> 00:18:20.720\nnarrative of what's the\n\n410\n00:18:20.720 --> 00:18:23.560\nmarket and what's our situation in the market and what's the problem to be\n\n411\n00:18:23.560 --> 00:18:24.560\nsolved or the job to be\n\n412\n00:18:24.560 --> 00:18:28.570\ndone. Then we have to articulate that vision of what could it be? What are we\n\n413\n00:18:28.570 --> 00:18:29.120\nstriving towards?\n\n414\n00:18:29.120 --> 00:18:32.580\nWhere are we trying to get to? And then the third thing is executing that plan,\n\n415\n00:18:32.580 --> 00:18:33.840\nbuilding and mobilizing\n\n416\n00:18:33.840 --> 00:18:37.560\nthe plan and the people to get there. So for me, it's always started with\n\n417\n00:18:37.560 --> 00:18:38.560\nclarity. If we don't\n\n418\n00:18:38.560 --> 00:18:41.530\nknow what problem we're solving, or we don't know who we're solving it for, we\n\n419\n00:18:41.530 --> 00:18:42.080\ncan do all these\n\n420\n00:18:42.080 --> 00:18:45.730\nother steps and they will not move the needle on our ultimate goals. And, you\n\n421\n00:18:45.730 --> 00:18:46.480\nknow, what you're\n\n422\n00:18:46.480 --> 00:18:49.510\nreally talking about is the first responsibility of leadership, which is to\n\n423\n00:18:49.510 --> 00:18:50.400\ndefine reality. The\n\n424\n00:18:50.400 --> 00:18:55.270\nreality of the workplace and then create these innovative solutions. Can you\n\n425\n00:18:55.270 --> 00:18:56.480\nshare an example of\n\n426\n00:18:56.480 --> 00:19:01.760\nwhere you provide a clarity on a really complex problem that really helped the\n\n427\n00:19:01.760 --> 00:19:03.280\ntrajectory of your\n\n428\n00:19:03.280 --> 00:19:10.230\ncompany? So in January of 2023, you know, basically two months after chat, GPT\n\n429\n00:19:10.230 --> 00:19:11.520\nhad started to land on\n\n430\n00:19:11.520 --> 00:19:16.200\nthe scene. We sat as a leadership team and had a discussion about what did AI\n\n431\n00:19:16.200 --> 00:19:17.200\nmean for our business.\n\n432\n00:19:17.200 --> 00:19:20.690\nSo, you know, if we remember at that time, two months in, tons of open\n\n433\n00:19:20.690 --> 00:19:22.000\nquestions,\n\n434\n00:19:22.000 --> 00:19:26.400\nplenty of healthy skepticism. There was a raging debate within our own team of,\n\n435\n00:19:26.400 --> 00:19:30.360\nshould we try to act on these kind of new technologies? Should we be\n\n436\n00:19:30.360 --> 00:19:31.600\nincorporating them into the roadmap\n\n437\n00:19:31.600 --> 00:19:34.930\nthat we just built for that year? You know, we just finished that whole\n\n438\n00:19:34.930 --> 00:19:35.840\nplanning process?\n\n439\n00:19:35.840 --> 00:19:39.250\nOr do we wait and see? And there were advocates on both sides. That was a\n\n440\n00:19:39.250 --> 00:19:40.480\nmoment where I felt it\n\n441\n00:19:40.480 --> 00:19:45.720\nwas critical to step in and really have a strong voice and clarity around my\n\n442\n00:19:45.720 --> 00:19:46.960\nview, which was this\n\n443\n00:19:46.960 --> 00:19:51.310\ntechnology will change everything. We have to be a first mover, not a last m\n\n444\n00:19:51.310 --> 00:19:52.560\nover here. We can't\n\n445\n00:19:52.560 --> 00:19:55.100\nwait to see what others are doing. And the only way we're going to be\n\n446\n00:19:55.100 --> 00:19:56.160\nsuccessful is if we get our\n\n447\n00:19:56.160 --> 00:19:59.410\nhands dirty and start to learn by doing. Now, at the same time, we couldn't\n\n448\n00:19:59.410 --> 00:20:00.320\njust throw out our whole\n\n449\n00:20:00.320 --> 00:20:04.130\nroadmap and start over again, because we had a ton of goals to achieve. We knew\n\n450\n00:20:04.130 --> 00:20:04.640\na bunch of\n\n451\n00:20:04.640 --> 00:20:08.480\nproblems we needed to solve with existing capabilities. So what we did was\n\n452\n00:20:08.480 --> 00:20:09.920\nisolate a small team to\n\n453\n00:20:09.920 --> 00:20:15.030\nbasically go offsite, essentially, in our kind of virtual mode and just focus\n\n454\n00:20:15.030 --> 00:20:16.080\non the question\n\n455\n00:20:16.880 --> 00:20:20.120\nhow will we build Upwork today and what would it look like if we built it prem\n\n456\n00:20:20.120 --> 00:20:21.200\nised on an AI\n\n457\n00:20:21.200 --> 00:20:25.600\nfoundation? And that work and that team came back with some incredible insights\n\n458\n00:20:25.600 --> 00:20:25.600\n,\n\n459\n00:20:25.600 --> 00:20:29.200\nhuge inspirations for us from a vision standpoint in terms of putting stakes in\n\n460\n00:20:29.200 --> 00:20:29.840\nthe ground of where\n\n461\n00:20:29.840 --> 00:20:33.930\nwe were going in the medium term. And then we gradually pulled pieces of that\n\n462\n00:20:33.930 --> 00:20:34.960\ninto the roadmap\n\n463\n00:20:34.960 --> 00:20:40.030\nand started to build chunks of that idea as part of our AI strategy. But that\n\n464\n00:20:40.030 --> 00:20:40.800\nwas a defining moment\n\n465\n00:20:40.800 --> 00:20:44.090\nfor us in terms of making that pivot and really committing to something that at\n\n466\n00:20:44.090 --> 00:20:44.960\nthe time,\n\n467\n00:20:44.960 --> 00:20:49.120\nthere were still a lot of question marks about. Yeah, you took this big swing\n\n468\n00:20:49.120 --> 00:20:50.800\nto basically what\n\n469\n00:20:50.800 --> 00:20:58.000\nyou guys describe, which I love this, is refound Upwork. And as an AI company,\n\n470\n00:20:58.000 --> 00:21:00.640\nwhen others hesitated,\n\n471\n00:21:00.640 --> 00:21:06.160\nhow did you get the personal courage to make that call? I think I faced a lot\n\n472\n00:21:06.160 --> 00:21:07.520\nof tests over the many\n\n473\n00:21:07.520 --> 00:21:11.330\nyears, not just leading this business, but also just rising up through a number\n\n474\n00:21:11.330 --> 00:21:12.320\nof roles. And\n\n475\n00:21:13.600 --> 00:21:18.400\nthere was one form of experience for sure that happened during the really when\n\n476\n00:21:18.400 --> 00:21:19.040\nthe outbreak of\n\n477\n00:21:19.040 --> 00:21:24.550\nthe Ukraine war started in February of 2022, where I think for me, that was\n\n478\n00:21:24.550 --> 00:21:25.920\nactually for our business,\n\n479\n00:21:25.920 --> 00:21:30.760\na significant crisis. We had 10 to 12% of our talent globally in the war torn\n\n480\n00:21:30.760 --> 00:21:32.160\nregion. We had 12%\n\n481\n00:21:32.160 --> 00:21:36.450\nof our own team internally that we work with also in that region. So we had\n\n482\n00:21:36.450 --> 00:21:37.680\ninternal exposure,\n\n483\n00:21:37.680 --> 00:21:41.520\nwe had customer exposure, revenue as it rests, like all of these things. And\n\n484\n00:21:41.520 --> 00:21:42.480\nmost importantly,\n\n485\n00:21:43.040 --> 00:21:47.120\nI was faced with the ethical question to some extent of do we continue to\n\n486\n00:21:47.120 --> 00:21:49.040\noperate in Russia and Belarus,\n\n487\n00:21:49.040 --> 00:21:53.660\nor not? And there were advocates from our customers on both sides, advocates\n\n488\n00:21:53.660 --> 00:21:55.040\ninternally on both sides.\n\n489\n00:21:55.040 --> 00:21:59.320\nUltimately, we were the first company in our space that made the decision to\n\n490\n00:21:59.320 --> 00:22:00.480\nsuspend operations\n\n491\n00:22:00.480 --> 00:22:04.440\nin Russia and Belarus. And that was an agonizing decision. Through that, I\n\n492\n00:22:04.440 --> 00:22:05.440\nthink I really learned\n\n493\n00:22:05.440 --> 00:22:09.030\nand felt that adage that it's lonely at the top, because there was no one who\n\n494\n00:22:09.030 --> 00:22:09.840\ncould tell me\n\n495\n00:22:10.480 --> 00:22:13.750\nwith any intelligence, like what really needed to happen. And only I had the\n\n496\n00:22:13.750 --> 00:22:14.240\ninformation and\n\n497\n00:22:14.240 --> 00:22:17.490\nperspective to make that really tough decision for our customers who were\n\n498\n00:22:17.490 --> 00:22:18.560\ndirectly impacted.\n\n499\n00:22:18.560 --> 00:22:22.560\nNow, our platform is a lifeline for so many of them. And so turning it off in a\n\n500\n00:22:22.560 --> 00:22:23.680\ncertain market\n\n501\n00:22:23.680 --> 00:22:28.240\nis extremely risky and goes against kind of our value system. At the same time,\n\n502\n00:22:28.240 --> 00:22:28.640\nwe knew we\n\n503\n00:22:28.640 --> 00:22:32.910\ncouldn't operate and deliver our brand value and our purpose in these markets,\n\n504\n00:22:32.910 --> 00:22:33.920\ngiven sanctions and\n\n505\n00:22:33.920 --> 00:22:37.260\nchanging conditions on the ground that just made it untenable. So this was a\n\n506\n00:22:37.260 --> 00:22:38.480\nvery difficult choice.\n\n507\n00:22:38.480 --> 00:22:43.380\nBut I think going through that and realizing the full responsibility that I had\n\n508\n00:22:43.380 --> 00:22:44.320\nto our customers\n\n509\n00:22:44.320 --> 00:22:48.000\nand making that decision with clarity early on so that they could all make\n\n510\n00:22:48.000 --> 00:22:48.800\ntheir own decisions\n\n511\n00:22:48.800 --> 00:22:52.130\ngoing from there. And we could continue to operate effectively as a team was\n\n512\n00:22:52.130 --> 00:22:53.040\nessential.\n\n513\n00:22:53.040 --> 00:22:57.040\nSo I think it's been moments like those, David, that really kind of tested us\n\n514\n00:22:57.040 --> 00:22:57.680\nand our leadership\n\n515\n00:22:57.680 --> 00:23:01.340\nand our cultural fabric and me in terms of making a bold and clear decision\n\n516\n00:23:01.340 --> 00:23:03.040\nearly. And I've always\n\n517\n00:23:03.040 --> 00:23:07.520\nseen that those types of decision-making moments play out better when you can\n\n518\n00:23:07.520 --> 00:23:08.320\nbe clear and move\n\n519\n00:23:08.320 --> 00:23:12.480\nfast and make a good decision versus wait and wait for more information, etc.\n\n520\n00:23:12.480 --> 00:23:16.560\nHey, everyone. It's Kula from How Leaders Lead. And if you've watched our\n\n521\n00:23:16.560 --> 00:23:17.520\npodcast for any number\n\n522\n00:23:17.520 --> 00:23:21.260\nof episodes, you probably know that a common theme from all of the great\n\n523\n00:23:21.260 --> 00:23:22.480\nleaders we interview\n\n524\n00:23:22.480 --> 00:23:26.840\nis that they are active learners. They had this commitment to continuing to\n\n525\n00:23:26.840 --> 00:23:27.920\nlearn and grow so\n\n526\n00:23:27.920 --> 00:23:31.630\nthat they don't say a statement and so that they continue to see success in\n\n527\n00:23:31.630 --> 00:23:32.560\ntheir leadership\n\n528\n00:23:32.560 --> 00:23:37.120\nand in their life. This theme of active learning is so important. And it's what\n\n529\n00:23:37.120 --> 00:23:38.240\nDavid's latest book\n\n530\n00:23:38.240 --> 00:23:42.720\nHow Leaders Learn is all about. It's all about helping you develop that skill\n\n531\n00:23:42.720 --> 00:23:43.600\nof active learning\n\n532\n00:23:43.600 --> 00:23:47.830\nso that you too can continue to see success in your leadership and in your life\n\n533\n00:23:47.830 --> 00:23:48.560\n. The book is\n\n534\n00:23:48.560 --> 00:23:52.730\nreally entertaining. It pulls stories from some of our greatest podcast guests\n\n535\n00:23:52.730 --> 00:23:53.440\nand pairs those\n\n536\n00:23:53.440 --> 00:23:57.570\nstories with insights that you can incorporate into your leadership and into\n\n537\n00:23:57.570 --> 00:23:58.960\nyour life right away.\n\n538\n00:23:58.960 --> 00:24:03.290\nGrab How Leaders Learn on Amazon or wherever books are sold. And I think you're\n\n539\n00:24:03.290 --> 00:24:04.080\nreally gonna love it.\n\n540\n00:24:04.080 --> 00:24:08.080\nYou feel David's personality through the pages and through history telling. And\n\n541\n00:24:08.080 --> 00:24:08.720\nit's a really\n\n542\n00:24:08.720 --> 00:24:13.010\npowerful way to level up your leadership. You know, AI is something every\n\n543\n00:24:13.010 --> 00:24:13.840\nleader is really\n\n544\n00:24:13.840 --> 00:24:17.370\nstruggling with right now or trying to get better, making it core competes for\n\n545\n00:24:17.370 --> 00:24:18.160\nthemselves and for\n\n546\n00:24:18.160 --> 00:24:24.840\ntheir organization. What are you personally doing to, you know, up your game in\n\n547\n00:24:24.840 --> 00:24:26.480\nthe world of AI?\n\n548\n00:24:26.480 --> 00:24:30.470\nHow have you gone about learning about it so that you can lead? I spent a lot\n\n549\n00:24:30.470 --> 00:24:32.000\nof time myself just\n\n550\n00:24:32.000 --> 00:24:37.160\nusing these different tools. You know, I'm a bid chat, chat GPT user. I\n\n551\n00:24:37.160 --> 00:24:38.080\nexperiment with Gemini a\n\n552\n00:24:38.080 --> 00:24:42.000\nlot. I haven't had as much success with that. And I look at it and test out\n\n553\n00:24:42.000 --> 00:24:44.080\nkind of category\n\n554\n00:24:44.080 --> 00:24:47.840\nspecific tools. So I'm not a developer, but I will watch tons of videos of how\n\n555\n00:24:47.840 --> 00:24:48.720\npeople are using\n\n556\n00:24:48.720 --> 00:24:52.740\ntools like cursor, V zero. Of course, I talk to our own team all the time about\n\n557\n00:24:52.740 --> 00:24:53.440\nthis because we\n\n558\n00:24:53.440 --> 00:24:57.430\nare using those tools internally. Bonus things come out. I'm constantly kind of\n\n559\n00:24:57.430 --> 00:24:57.920\nreading,\n\n560\n00:24:57.920 --> 00:25:02.050\nexperimenting, watching and participating in keeping my own AI still sharp\n\n561\n00:25:02.050 --> 00:25:03.040\nbecause I have to roll\n\n562\n00:25:03.040 --> 00:25:06.500\nthat model out for my team. You know, no one of my companies going to believe\n\n563\n00:25:06.500 --> 00:25:06.960\nthat I'm serious\n\n564\n00:25:06.960 --> 00:25:10.690\nabout AI unless I'm showing up using these tools, pushing on them where they're\n\n565\n00:25:10.690 --> 00:25:11.680\nnot using the tools,\n\n566\n00:25:11.680 --> 00:25:15.360\netc. Of course, we also have some programmatic things in place. We started an\n\n567\n00:25:15.360 --> 00:25:16.080\nAI application\n\n568\n00:25:16.080 --> 00:25:19.280\nprogram where we have a bunch of initiatives that are really focused on, you\n\n569\n00:25:19.280 --> 00:25:20.320\nknow, targeting\n\n570\n00:25:20.320 --> 00:25:25.040\nand unlocking this value. But personally, I feel I need to champion this both\n\n571\n00:25:25.040 --> 00:25:25.840\nby doing\n\n572\n00:25:25.840 --> 00:25:29.120\nand showing up with our teams to really advocate for our AI adoption.\n\n573\n00:25:29.120 --> 00:25:33.440\nHas it been a challenge for you to take people with you in the company to get\n\n574\n00:25:33.440 --> 00:25:34.560\nbehind this movement?\n\n575\n00:25:34.560 --> 00:25:38.780\nOr is it been something that people have easily gravitated to because you're we\n\n576\n00:25:38.780 --> 00:25:39.280\n're obviously\n\n577\n00:25:39.280 --> 00:25:44.000\nchanging old habits by getting used to this? Totally. And we've seen everything\n\n578\n00:25:44.000 --> 00:25:44.480\ninternally.\n\n579\n00:25:44.480 --> 00:25:49.650\nYou know, we've we always had kind of this cohort of early adopters who were,\n\n580\n00:25:49.650 --> 00:25:49.920\nyou know,\n\n581\n00:25:49.920 --> 00:25:54.290\nleaning in advocating. We've bought two AI companies in the last two years. So\n\n582\n00:25:54.290 --> 00:25:54.400\nthat's\n\n583\n00:25:54.400 --> 00:25:58.480\nbrought in a lot of like super forward leaning AI talent, including our head of\n\n584\n00:25:58.480 --> 00:25:59.520\nAI, who came in\n\n585\n00:25:59.520 --> 00:26:02.560\nfrom one of those acquisitions. But you're right, there's also a long tail of\n\n586\n00:26:02.560 --> 00:26:03.360\nother people who've\n\n587\n00:26:03.360 --> 00:26:07.010\nbeen worried or skeptical or feel like maybe they don't have permission to use\n\n588\n00:26:07.010 --> 00:26:08.000\nthese tools. So\n\n589\n00:26:08.000 --> 00:26:12.130\nwe make it a constant habit every week. We're talking in our we have a weekly\n\n590\n00:26:12.130 --> 00:26:13.040\nkind of mini\n\n591\n00:26:13.040 --> 00:26:17.600\nall hands meeting. We're talking about and showcasing how people are internally\n\n592\n00:26:17.600 --> 00:26:18.080\nusing these\n\n593\n00:26:18.080 --> 00:26:22.040\ntools. We've created workshops and webinars and now really communicated to\n\n594\n00:26:22.040 --> 00:26:22.800\neveryone that the\n\n595\n00:26:22.800 --> 00:26:26.830\nexpectation is they are using these tools. So it has taken, you know, in some\n\n596\n00:26:26.830 --> 00:26:27.440\nplaces kind of the\n\n597\n00:26:27.440 --> 00:26:30.680\nsnowball needed to start rolling before speeding up. But now it feels like it's\n\n598\n00:26:30.680 --> 00:26:32.080\nmoving really fast\n\n599\n00:26:32.080 --> 00:26:35.830\nin terms of executing on this like opportunity and getting everyone in the\n\n600\n00:26:35.830 --> 00:26:37.280\ncompany involved in it.\n\n601\n00:26:37.280 --> 00:26:41.360\nHow important has it been for you to make it clear to everybody that this is a\n\n602\n00:26:41.360 --> 00:26:42.080\nthis is a bus\n\n603\n00:26:42.080 --> 00:26:46.470\neverybody's got to get on? It's my top priority. It has been so important\n\n604\n00:26:46.470 --> 00:26:47.520\nbecause you're right,\n\n605\n00:26:47.520 --> 00:26:51.280\nthere's skepticism, there's fear, people worry even in our company about their\n\n606\n00:26:51.280 --> 00:26:52.240\njobs being replaced\n\n607\n00:26:52.240 --> 00:26:57.040\nby AI. I mean, this is a widespread phenomenon. So I have had to be very clear\n\n608\n00:26:57.040 --> 00:26:57.840\nand it's one of\n\n609\n00:26:57.840 --> 00:27:00.540\nthose things like repeat, repeat, repeat until people are sick of hearing it\n\n610\n00:27:00.540 --> 00:27:01.440\nand I'm sick of hearing\n\n611\n00:27:01.440 --> 00:27:06.120\nmyself say it, but repeat what our goals are and really reassure people as well\n\n612\n00:27:06.120 --> 00:27:06.960\nas push them and\n\n613\n00:27:06.960 --> 00:27:09.850\nchallenge them in terms of where we're going going. And this is I think\n\n614\n00:27:09.850 --> 00:27:11.040\nessential for every leader.\n\n615\n00:27:11.040 --> 00:27:14.050\nIt's not going to happen in the business without each of us really leaning in\n\n616\n00:27:14.050 --> 00:27:15.520\nand driving this change.\n\n617\n00:27:15.520 --> 00:27:19.760\nYou know, you're obviously a leader who can clarify and you've done that many,\n\n618\n00:27:19.760 --> 00:27:20.560\nmany times. You're a\n\n619\n00:27:20.560 --> 00:27:26.720\ngreat communicator and you have these obvious skills and you're at the top of\n\n620\n00:27:26.720 --> 00:27:27.600\nan organization,\n\n621\n00:27:27.600 --> 00:27:31.840\nwhich I think is fantastic. And you're a great example for my daughter and so\n\n622\n00:27:31.840 --> 00:27:32.400\nmany others.\n\n623\n00:27:32.400 --> 00:27:40.080\nDid you ever find being a female really inhibited your ability to take on\n\n624\n00:27:40.080 --> 00:27:41.200\nopportunities or even\n\n625\n00:27:41.200 --> 00:27:45.850\nget opportunities? And if so, how'd you work through it? I used to be very\n\n626\n00:27:45.850 --> 00:27:46.960\nnaive on this topic.\n\n627\n00:27:46.960 --> 00:27:51.600\nWhen I was 22, I'm a Kinsey or Microsoft, I was thinking, it doesn't matter\n\n628\n00:27:51.600 --> 00:27:52.160\nthat I'm a woman,\n\n629\n00:27:52.160 --> 00:27:55.100\nlike that's not going to hold me back and was going to penalize me for that.\n\n630\n00:27:55.100 --> 00:27:55.680\nAnd of course,\n\n631\n00:27:55.680 --> 00:28:00.560\nin the last 20 years, I've seen tons of instances where I'm underestimated, I'm\n\n632\n00:28:00.560 --> 00:28:01.120\nlooked over,\n\n633\n00:28:01.120 --> 00:28:05.920\nI'm man-splained to constantly just because, you know, people think, oh, she\n\n634\n00:28:05.920 --> 00:28:06.320\ncan't know what\n\n635\n00:28:06.320 --> 00:28:09.370\nshe's doing or she can't take this on. So of course, I've experienced that\n\n636\n00:28:09.370 --> 00:28:10.560\nthroughout my career.\n\n637\n00:28:11.120 --> 00:28:16.480\nI think the thing that has been, you know, really interesting as the CEO, I've\n\n638\n00:28:16.480 --> 00:28:17.280\nreally realized that\n\n639\n00:28:17.280 --> 00:28:21.840\nin our culture, there's kind of two types of women leaders who are stereotyped.\n\n640\n00:28:21.840 --> 00:28:22.560\nThere's kind of the\n\n641\n00:28:22.560 --> 00:28:26.170\nmom who's like soft and fuzzy, but maybe like a little clueless or can't make\n\n642\n00:28:26.170 --> 00:28:27.760\nthose hard decisions.\n\n643\n00:28:27.760 --> 00:28:31.180\nAnd then there's a call her the jerk, you know, the person who's like cold-\n\n644\n00:28:31.180 --> 00:28:32.240\nhearted, like doesn't\n\n645\n00:28:32.240 --> 00:28:37.250\ncare, like, you know, just breaking glass everywhere. And I am neither of those\n\n646\n00:28:37.250 --> 00:28:38.880\nthings. I bring a lot\n\n647\n00:28:38.880 --> 00:28:43.270\nof warmth and love and caring that's genuine for my team and our customers. I'm\n\n648\n00:28:43.270 --> 00:28:44.400\nalso hard-driving\n\n649\n00:28:44.400 --> 00:28:48.270\nand decisive and bold and analytical. And people don't know what to do with\n\n650\n00:28:48.270 --> 00:28:49.280\nthat. I think they\n\n651\n00:28:49.280 --> 00:28:55.460\noften can only kind of look for, see one, not both of those things at best. So\n\n652\n00:28:55.460 --> 00:28:56.640\nit's become clear to\n\n653\n00:28:56.640 --> 00:29:00.730\nme that I need to do a lot to communicate, as you mentioned, and really show up\n\n654\n00:29:00.730 --> 00:29:01.600\nand try to educate\n\n655\n00:29:01.600 --> 00:29:05.320\nmy team and our stakeholders in terms of who I am and what I stand for because\n\n656\n00:29:05.320 --> 00:29:06.000\nthe stereotypes\n\n657\n00:29:06.000 --> 00:29:09.440\nthat people really fall into, especially for women leaders, just don't apply.\n\n658\n00:29:09.440 --> 00:29:14.750\nWhat specific advice would you give to a female that maybe you wouldn't give to\n\n659\n00:29:14.750 --> 00:29:16.560\na male that\n\n660\n00:29:16.560 --> 00:29:21.170\ncould help them, you know, climb the ladder? Unfortunately, a lot of women who\n\n661\n00:29:21.170 --> 00:29:22.480\nare so capable\n\n662\n00:29:22.480 --> 00:29:27.590\nand the studies have shown this hold themselves back from that next step\n\n663\n00:29:27.590 --> 00:29:28.640\nbecause they feel like,\n\n664\n00:29:28.640 --> 00:29:31.680\nah, they need to do a little more, you know, prove themselves a little more or\n\n665\n00:29:31.680 --> 00:29:32.400\nlearn a little more\n\n666\n00:29:32.400 --> 00:29:36.040\nor go do that other job before they do the job they want to do. And a piece of\n\n667\n00:29:36.040 --> 00:29:37.200\nadvice I give to a\n\n668\n00:29:37.200 --> 00:29:41.740\nlot of folks that come to me and we chat is if you're thinking about going to\n\n669\n00:29:41.740 --> 00:29:42.480\nthat thing,\n\n670\n00:29:42.480 --> 00:29:46.250\ndon't do the three things first. Like go do that thing now. You're ready. You\n\n671\n00:29:46.250 --> 00:29:47.680\n're capable. Go do it.\n\n672\n00:29:47.680 --> 00:29:50.360\nThat's what that's what a lot of men do. They don't wait until, you know, they\n\n673\n00:29:50.360 --> 00:29:51.520\nhave that perfect\n\n674\n00:29:51.520 --> 00:29:54.010\nprofile or capability. And I think that's something that as women we can\n\n675\n00:29:54.010 --> 00:29:55.280\nconstantly push ourselves on\n\n676\n00:29:55.280 --> 00:29:59.690\nbecause our culture doesn't necessarily foster that in us. Yeah, I agree. And,\n\n677\n00:29:59.690 --> 00:30:01.280\nyou know, it's great to see\n\n678\n00:30:01.280 --> 00:30:07.040\nthat you're leading the way and showing people that it can be done in the very\n\n679\n00:30:07.040 --> 00:30:07.840\nbest way. So\n\n680\n00:30:07.840 --> 00:30:13.920\ncongratulations on that. And, you know, your company provides a great service\n\n681\n00:30:13.920 --> 00:30:15.920\nto your customers.\n\n682\n00:30:15.920 --> 00:30:20.560\nAnd I was just curious, you know, what advice can you give on how to balance\n\n683\n00:30:20.560 --> 00:30:21.680\nbetween full-time\n\n684\n00:30:21.680 --> 00:30:27.600\nemployees and freelancers? And maybe you could use Upwork as an example.\n\n685\n00:30:28.320 --> 00:30:33.720\nWe have about three quarters of our workforce today is freelancers. And that's\n\n686\n00:30:33.720 --> 00:30:34.080\nbeen true\n\n687\n00:30:34.080 --> 00:30:37.770\nbasically since we were born as a small startup. We've always built our\n\n688\n00:30:37.770 --> 00:30:38.960\nworkforce as hybrid.\n\n689\n00:30:38.960 --> 00:30:45.440\nAnd what we see today in the environment more broadly is a shift where more and\n\n690\n00:30:45.440 --> 00:30:46.400\nmore companies\n\n691\n00:30:46.400 --> 00:30:50.640\nare looking critically at their full-time employee staff and realizing the\n\n692\n00:30:50.640 --> 00:30:51.920\nlimitations of what that\n\n693\n00:30:51.920 --> 00:30:56.220\nstaff can do for them. Often those people on their current payroll don't know\n\n694\n00:30:56.220 --> 00:30:57.360\nhow to use AI tools\n\n695\n00:30:57.360 --> 00:31:00.480\naren't maybe moving fast enough up the learning curve. I don't have other\n\n696\n00:31:00.480 --> 00:31:01.520\ncritical skills as these\n\n697\n00:31:01.520 --> 00:31:05.600\nbusinesses are moving in a very dynamic environment. So that trend is causing\n\n698\n00:31:05.600 --> 00:31:06.800\nmore companies to have a\n\n699\n00:31:06.800 --> 00:31:12.600\nsmaller core FTE group and a larger group of contingent freelance and kind of\n\n700\n00:31:12.600 --> 00:31:13.680\nthird-party\n\n701\n00:31:13.680 --> 00:31:16.100\nvendors that they work with. And that I think is an enduring shift we're going\n\n702\n00:31:16.100 --> 00:31:16.960\nto keep seeing more of.\n\n703\n00:31:16.960 --> 00:31:23.040\nSo for every company, I think the key is moving from a mindset of I, you know,\n\n704\n00:31:23.040 --> 00:31:23.920\nin the past, like\n\n705\n00:31:23.920 --> 00:31:27.900\nmost leaders have thought like, oh, I hire or I do work with the unit of the F\n\n706\n00:31:27.900 --> 00:31:28.720\nTE. That's like the\n\n707\n00:31:28.720 --> 00:31:32.180\nunit of measurement. Like I need to add these FTEs or subtract these FTEs. That\n\n708\n00:31:32.180 --> 00:31:32.880\n's how work is\n\n709\n00:31:32.880 --> 00:31:37.830\ncomprised. The shift for leaders is to say these are FTE units. Now it's skills\n\n710\n00:31:37.830 --> 00:31:39.760\nor projects or efforts.\n\n711\n00:31:39.760 --> 00:31:43.490\nAnd once we break down the work to be more clear about what those boundaries\n\n712\n00:31:43.490 --> 00:31:44.560\nand goals are,\n\n713\n00:31:44.560 --> 00:31:47.680\nwe actually may not need a big team of 10 FTEs. Maybe we could have four or\n\n714\n00:31:47.680 --> 00:31:48.720\nfive specialists who\n\n715\n00:31:48.720 --> 00:31:51.900\nreally focus on that project and then we keep going with them or disband it\n\n716\n00:31:51.900 --> 00:31:53.040\nbased on what we find.\n\n717\n00:31:53.040 --> 00:31:57.040\nAnd so it's a different mindset around kind of what the unit of work is, how\n\n718\n00:31:57.040 --> 00:31:57.680\nyou define and\n\n719\n00:31:57.680 --> 00:32:01.100\nscope the work, and then of course going to this tremendous pool of freelancers\n\n720\n00:32:01.100 --> 00:32:02.160\n, which is a $1.3\n\n721\n00:32:02.160 --> 00:32:06.800\ntrillion economy in the US alone to find that skilled talent that you probably\n\n722\n00:32:06.800 --> 00:32:07.680\ndon't have to be\n\n723\n00:32:07.680 --> 00:32:12.160\nmoving fast enough and agile, most agile in this current environment.\n\n724\n00:32:12.160 --> 00:32:17.700\nAnd how do you go about defining the scope of a job so that you can decide,\n\n725\n00:32:17.700 --> 00:32:18.960\nokay, it's a full-time\n\n726\n00:32:18.960 --> 00:32:23.230\nemployee or it's a freelancer. I mean, do you have a process that you use to\n\n727\n00:32:23.230 --> 00:32:24.080\nget at that?\n\n728\n00:32:24.080 --> 00:32:28.880\nWe do. I mean, we start with really what's the goal here and what's the time\n\n729\n00:32:28.880 --> 00:32:29.520\nframe which we need\n\n730\n00:32:29.520 --> 00:32:33.120\nto achieve the goal? And is this something that's going to endure beyond that\n\n731\n00:32:33.120 --> 00:32:34.240\nor not? We also look\n\n732\n00:32:34.240 --> 00:32:38.940\nat aspects of course that are around kind of compliance and how much control\n\n733\n00:32:38.940 --> 00:32:39.920\nand direction\n\n734\n00:32:39.920 --> 00:32:42.820\ndo we have to give to this work or is it more kind of autonomous and we can\n\n735\n00:32:42.820 --> 00:32:43.680\nshare context and\n\n736\n00:32:43.680 --> 00:32:47.320\nthat have experts go off and do some of this work for them. So these are two of\n\n737\n00:32:47.320 --> 00:32:48.320\nthe factors that we\n\n738\n00:32:48.320 --> 00:32:53.640\nlook at in figuring out, you know, can we do this with with freelance talent?\n\n739\n00:32:53.640 --> 00:32:54.480\nBut for us, David,\n\n740\n00:32:54.480 --> 00:32:57.760\nbasically every question kind of starts with the premise like, why can't you do\n\n741\n00:32:57.760 --> 00:32:58.320\nit with freelance\n\n742\n00:32:58.320 --> 00:33:01.270\ntalent? Like that's where we always start is like, this should be something we\n\n743\n00:33:01.270 --> 00:33:02.400\ncan do with a flexible\n\n744\n00:33:02.400 --> 00:33:05.690\nteam. And we really push ourselves to say in places where people want more head\n\n745\n00:33:05.690 --> 00:33:06.240\ncount like,\n\n746\n00:33:06.240 --> 00:33:09.980\nis that necessary? And they really have a high bar to justify in order to make\n\n747\n00:33:09.980 --> 00:33:10.800\nthat happen.\n\n748\n00:33:10.800 --> 00:33:14.960\nThat makes sense. And as I said at the top of the show, you know, you've been\n\n749\n00:33:14.960 --> 00:33:16.800\nleading in this\n\n750\n00:33:16.800 --> 00:33:20.800\nremote work environment before people even talked about remote work\n\n751\n00:33:20.800 --> 00:33:22.080\nenvironments and\n\n752\n00:33:22.080 --> 00:33:27.280\neven doing this a long time. And it's now the new normal for every company.\n\n753\n00:33:27.280 --> 00:33:28.960\nWhat advice would you\n\n754\n00:33:28.960 --> 00:33:35.050\ngive others on how to navigate this well? And how do you really be a company\n\n755\n00:33:35.050 --> 00:33:36.640\nthat knows how to\n\n756\n00:33:36.640 --> 00:33:43.040\ndelete a remote workforce? The first thing is, I think too often people mistake\n\n757\n00:33:43.040 --> 00:33:43.920\na remote first,\n\n758\n00:33:43.920 --> 00:33:48.960\na remote forward workforce with, we don't get together in person. When in fact,\n\n759\n00:33:48.960 --> 00:33:49.440\nour model has\n\n760\n00:33:49.440 --> 00:33:53.350\nalways been a combination of yes, lots of fully remote team members, lots of\n\n761\n00:33:53.350 --> 00:33:54.400\nflexibility in terms\n\n762\n00:33:54.400 --> 00:33:57.950\nof when, where and how people work. But we still have strong cadences of\n\n763\n00:33:57.950 --> 00:33:59.600\ngetting teams together.\n\n764\n00:33:59.600 --> 00:34:04.280\nSo they really build not just business context, but also social context and\n\n765\n00:34:04.280 --> 00:34:05.120\nrelationships. And\n\n766\n00:34:05.120 --> 00:34:08.780\nthat is really a huge unlock for remote teams. They have to have that as a\n\n767\n00:34:08.780 --> 00:34:10.800\nfoundation. So remote\n\n768\n00:34:10.800 --> 00:34:14.320\nteams have to have a lot of in-person touch points can vary based on the team\n\n769\n00:34:14.320 --> 00:34:14.640\nand the work,\n\n770\n00:34:14.640 --> 00:34:17.920\nbut that's a key part of relationship building. And then you also need to be\n\n771\n00:34:17.920 --> 00:34:18.560\nvery clear about\n\n772\n00:34:18.560 --> 00:34:22.460\nwhat are their remote work practices. So for example, in our company, in every\n\n773\n00:34:22.460 --> 00:34:23.280\nmeeting,\n\n774\n00:34:23.280 --> 00:34:27.280\ncameras are on for every participant. And that is really the guiding light as\n\n775\n00:34:27.280 --> 00:34:28.000\njust one example,\n\n776\n00:34:28.000 --> 00:34:31.790\nkind of practically, of how we ensure people are like seeing and hearing from\n\n777\n00:34:31.790 --> 00:34:32.000\neach other,\n\n778\n00:34:32.000 --> 00:34:35.500\nable to read body language. It's not about just dialing on the phone. You have\n\n779\n00:34:35.500 --> 00:34:36.560\nto be like physically\n\n780\n00:34:36.560 --> 00:34:41.490\npresent. Those are some of the things that we do. In addition to weekly touch\n\n781\n00:34:41.490 --> 00:34:42.000\npoints where you\n\n782\n00:34:42.000 --> 00:34:45.070\nbuild culture, you've got to build culture with a remote team that's not in the\n\n783\n00:34:45.070 --> 00:34:45.440\noffice.\n\n784\n00:34:45.440 --> 00:34:49.280\nAnd for us, that means things like a half hour touch point every week where we\n\n785\n00:34:49.280 --> 00:34:49.840\ncan put our\n\n786\n00:34:49.840 --> 00:34:54.300\nculture on display, showcase work that's happening, create context, and also\n\n787\n00:34:54.300 --> 00:34:55.440\nlet people see and hear\n\n788\n00:34:55.440 --> 00:34:58.110\nabout things that are happening across the business that they're not hearing\n\n789\n00:34:58.110 --> 00:34:58.880\nabout when they're not\n\n790\n00:34:58.880 --> 00:35:02.150\nin an office, which is what most of our team is. So those are some of the\n\n791\n00:35:02.150 --> 00:35:02.960\nthings that really have\n\n792\n00:35:02.960 --> 00:35:06.660\nhelped us build remote culture and remote fabric. But every company has to\n\n793\n00:35:06.660 --> 00:35:07.760\napproach this for like\n\n794\n00:35:07.760 --> 00:35:11.250\nwhat's right for them. We'll be back with the rest of my conversation with\n\n795\n00:35:11.250 --> 00:35:12.320\nHayden Brown in just a\n\n796\n00:35:12.320 --> 00:35:17.310\nmoment. Like Hayden, the co-founders of Warby Parker know how important it is\n\n797\n00:35:17.310 --> 00:35:18.160\nto move fast.\n\n798\n00:35:18.160 --> 00:35:23.280\nAnd for them, agility starts with fast, open, streamlined communication.\n\n799\n00:35:23.280 --> 00:35:30.730\nWe found that to be successful and to grow quickly, right, information has to\n\n800\n00:35:30.730 --> 00:35:31.200\nflow quickly\n\n801\n00:35:31.200 --> 00:35:35.440\nwithin the organization. And similarly, it's got to flow quickly between the\n\n802\n00:35:35.440 --> 00:35:36.160\ntwo of us, right? We\n\n803\n00:35:36.160 --> 00:35:39.690\nneed to model the behavior that we want to take place throughout the\n\n804\n00:35:39.690 --> 00:35:41.840\norganization. So we also,\n\n805\n00:35:41.840 --> 00:35:44.670\nour office is an open layout. We sit right next to each other in between\n\n806\n00:35:44.670 --> 00:35:46.160\nmeetings. We're often,\n\n807\n00:35:46.160 --> 00:35:51.040\nyou know, sharing notes with one another. Sometimes we're the first people that\n\n808\n00:35:51.040 --> 00:35:51.680\nwe talk to in the\n\n809\n00:35:51.680 --> 00:35:55.090\nmorning. And the last person we talk to at night, I don't know how much our\n\n810\n00:35:55.090 --> 00:35:57.120\nwives love that. But again,\n\n811\n00:35:57.120 --> 00:36:02.880\nto be a high growth company, right, you got to make quick decisions. And if\n\n812\n00:36:02.880 --> 00:36:03.680\nthose are going to be\n\n813\n00:36:03.680 --> 00:36:06.680\ngood decisions, they have to be informed decisions, which means information\n\n814\n00:36:06.680 --> 00:36:08.240\nneeds to travel quickly.\n\n815\n00:36:08.240 --> 00:36:13.950\nAnd we think that our competitive advantage is having the best data, having the\n\n816\n00:36:13.950 --> 00:36:15.040\nbest information\n\n817\n00:36:15.040 --> 00:36:21.040\nand having that flow throughout the company across functional groups that are\n\n818\n00:36:21.040 --> 00:36:22.480\nin other companies\n\n819\n00:36:22.480 --> 00:36:26.000\noften don't talk to each other or don't even exist within the same company,\n\n820\n00:36:26.000 --> 00:36:27.040\nright? And that's our\n\n821\n00:36:27.040 --> 00:36:30.340\ncompetitive advantage. We have direct relationships with our customers because\n\n822\n00:36:30.340 --> 00:36:31.200\nwe sell direct to\n\n823\n00:36:31.200 --> 00:36:36.400\nour customers through our stores and our website and our apps. So we're able to\n\n824\n00:36:36.400 --> 00:36:37.760\nget all this customer\n\n825\n00:36:37.760 --> 00:36:42.120\nfeedback and data. And then we disseminate it quickly across the company,\n\n826\n00:36:42.120 --> 00:36:43.440\nwhether it's to I\n\n827\n00:36:43.440 --> 00:36:48.480\nwear design or our merchants or to the technology team or to the CX team or to\n\n828\n00:36:48.480 --> 00:36:49.600\nthe marketing team,\n\n829\n00:36:49.600 --> 00:36:52.880\nright? And then we're able to sort of move nimbly and quickly.\n\n830\n00:36:52.880 --> 00:36:58.800\nGo back and listen to my entire conversation with co CEOs, Neil Blumenthal and\n\n831\n00:36:58.800 --> 00:36:59.760\nDave Gilboa,\n\n832\n00:36:59.760 --> 00:37:07.710\nepisode 181 here on Howl Eaters Lead. What have you learned about managing\n\n833\n00:37:07.710 --> 00:37:08.240\nconflict\n\n834\n00:37:08.240 --> 00:37:13.520\nin a remote environment? You know, you talked about the body language and you\n\n835\n00:37:13.520 --> 00:37:15.040\nknow, but you know,\n\n836\n00:37:15.840 --> 00:37:19.840\nhow do you how do you have wrestled tough things to the ground in a remote\n\n837\n00:37:19.840 --> 00:37:20.800\nenvironment? So it's not\n\n838\n00:37:20.800 --> 00:37:25.600\njust a telling kind of back and forth mode that way. Two things have really\n\n839\n00:37:25.600 --> 00:37:27.600\nhelped us. So one is\n\n840\n00:37:27.600 --> 00:37:31.150\nthe in person relationship building, which again, it's about dinners. It's\n\n841\n00:37:31.150 --> 00:37:32.240\nabout going on hikes.\n\n842\n00:37:32.240 --> 00:37:36.840\nLike when teams get together, they focus on that. That social fabric then\n\n843\n00:37:36.840 --> 00:37:37.920\nbuilds the psychological\n\n844\n00:37:37.920 --> 00:37:42.080\nsafety that people can have conflict with each other and feel like that's okay.\n\n845\n00:37:42.080 --> 00:37:42.480\nAnd also when\n\n846\n00:37:42.480 --> 00:37:46.340\nthey hear, you know, a challenge or a pushback from a colleague, they can know,\n\n847\n00:37:46.340 --> 00:37:46.800\noh, that's coming\n\n848\n00:37:46.800 --> 00:37:49.750\nfrom a place of positive intent because we talked over dinner and he's a super\n\n849\n00:37:49.750 --> 00:37:50.400\nnice guy. And he's\n\n850\n00:37:50.400 --> 00:37:52.880\nonly saying that's because he really thinks it's better for the business. So\n\n851\n00:37:52.880 --> 00:37:54.320\nlet's hash it out. So\n\n852\n00:37:54.320 --> 00:37:57.920\npositive intent and psychological safety comes from that relationship building.\n\n853\n00:37:57.920 --> 00:37:59.120\nThe other piece\n\n854\n00:37:59.120 --> 00:38:03.530\nof it, which I talk a lot with our executive team about is you can't have like\n\n855\n00:38:03.530 --> 00:38:04.480\none dimension of\n\n856\n00:38:04.480 --> 00:38:08.250\ncommunication. It can't be, you know, only scheduled meetings. When there's a\n\n857\n00:38:08.250 --> 00:38:09.920\nconflict, we have an\n\n858\n00:38:09.920 --> 00:38:13.120\nagreement that we will resolve things quickly. So we'll turn around, we'll get\n\n859\n00:38:13.120 --> 00:38:13.600\non the phone\n\n860\n00:38:13.600 --> 00:38:17.090\nright away or we'll set up an in person meeting right away or we'll take action\n\n861\n00:38:17.090 --> 00:38:17.600\nso that these\n\n862\n00:38:17.600 --> 00:38:21.950\nthings don't fester and become, you know, out of proportion or bigger conflicts\n\n863\n00:38:21.950 --> 00:38:22.880\n. It's about\n\n864\n00:38:22.880 --> 00:38:26.240\nuse whatever tool necessary to kind of bottom this out immediately and don't\n\n865\n00:38:26.240 --> 00:38:27.280\nlet it wait. So never\n\n866\n00:38:27.280 --> 00:38:30.460\nlike let a conflict roll into the next week, for example, it resolved it by\n\n867\n00:38:30.460 --> 00:38:31.040\nFriday.\n\n868\n00:38:31.040 --> 00:38:34.570\nMaybe that's part of your build and break approach, you know, you're building\n\n869\n00:38:34.570 --> 00:38:35.440\nthe culture and you\n\n870\n00:38:35.440 --> 00:38:38.660\nhave to break down the barriers when you see them. Totally. And that's why as a\n\n871\n00:38:38.660 --> 00:38:39.360\nproduct manager,\n\n872\n00:38:39.360 --> 00:38:43.260\nI love this job. Like I now get to build the company, not just the product. And\n\n873\n00:38:43.260 --> 00:38:44.960\nto me, that is everything.\n\n874\n00:38:44.960 --> 00:38:48.260\nSpeaking of that, you were a product manager. Now you're the CEO, you run every\n\n875\n00:38:48.260 --> 00:38:49.360\nfunction, you know,\n\n876\n00:38:49.360 --> 00:38:55.090\nhow did you broaden yourself? I'm a huge learner and I'm hugely curious. So I'm\n\n877\n00:38:55.090 --> 00:38:56.240\nalways asking other\n\n878\n00:38:56.240 --> 00:39:00.370\npeople for tips, advice, input, you know, reaching out to broaden my network\n\n879\n00:39:00.370 --> 00:39:01.920\nand really learn about\n\n880\n00:39:01.920 --> 00:39:05.290\nthe things that are the next kind of challenges in the role. So I had the good\n\n881\n00:39:05.290 --> 00:39:06.160\nfortune of doing a\n\n882\n00:39:06.160 --> 00:39:11.220\nlot of product marketing, you know, some other things before I became the CEO.\n\n883\n00:39:11.220 --> 00:39:11.920\nBut I've also\n\n884\n00:39:11.920 --> 00:39:16.590\nrealized there's nothing like trial by fire. And sometimes you can prepare, you\n\n885\n00:39:16.590 --> 00:39:17.200\ncan learn,\n\n886\n00:39:17.200 --> 00:39:20.560\nbut then you just have to go and do it. You have to get into it and you learn a\n\n887\n00:39:20.560 --> 00:39:21.280\nlot by doing,\n\n888\n00:39:21.280 --> 00:39:24.100\nyou know, that would be like my first earnings call. I had never let an\n\n889\n00:39:24.100 --> 00:39:25.040\nearnings call before,\n\n890\n00:39:25.040 --> 00:39:28.490\nbut I prepared, I practiced, I kind of thought through it. And actually then I\n\n891\n00:39:28.490 --> 00:39:29.520\ntook like a giant\n\n892\n00:39:29.520 --> 00:39:32.600\nrisk and surprise the street with some announcements they weren't expecting and\n\n893\n00:39:32.600 --> 00:39:33.440\nit paid off. It totally\n\n894\n00:39:33.440 --> 00:39:37.040\nworked. But you know, at some point you have to kind of set aside this idea\n\n895\n00:39:37.040 --> 00:39:38.160\nthat everyone else\n\n896\n00:39:38.160 --> 00:39:40.540\nknows better, kind of like what I learned at McKinsey, like everyone else is\n\n897\n00:39:40.540 --> 00:39:41.680\nmore expert. I learned,\n\n898\n00:39:41.680 --> 00:39:45.280\nyou know, everyone's kind of making it up. And so it's okay to learn, be smart,\n\n899\n00:39:45.280 --> 00:39:45.840\nstart with first\n\n900\n00:39:45.840 --> 00:39:49.720\nprinciples, and then go and apply that knowledge and then rinse and repeat. Now\n\n901\n00:39:49.720 --> 00:39:50.160\nyou're a very\n\n902\n00:39:50.160 --> 00:39:53.840\nconfident person, but is there been a time where you really had some\n\n903\n00:39:53.840 --> 00:39:56.880\nsignificant doubt? And if so,\n\n904\n00:39:56.880 --> 00:40:03.040\nhow did you work through it? Could you share that? So two months into the job\n\n905\n00:40:03.040 --> 00:40:04.160\nas the new CEO,\n\n906\n00:40:04.160 --> 00:40:07.810\nand mind you, I stepped into a context that was, you know, we were about one\n\n907\n00:40:07.810 --> 00:40:09.200\nyear post public,\n\n908\n00:40:09.200 --> 00:40:13.040\nour stock price had been faltering, investors had some questions, I was put in\n\n909\n00:40:13.040 --> 00:40:13.840\nas this new CEO,\n\n910\n00:40:13.840 --> 00:40:17.350\nthey didn't know yet. And I had a clear idea of what we needed to do with the\n\n911\n00:40:17.350 --> 00:40:18.000\nbusiness,\n\n912\n00:40:18.000 --> 00:40:22.430\nbut some of the things I felt we needed to do were very risky. So I laid out my\n\n913\n00:40:22.430 --> 00:40:23.360\nstrategy and\n\n914\n00:40:23.360 --> 00:40:27.600\nmy plan to the team, but part of that was saying, we have to act like we're in\n\n915\n00:40:27.600 --> 00:40:28.800\nwartime, we have to\n\n916\n00:40:28.800 --> 00:40:32.900\nwork a lot harder, the bar for excellence is now going up. And this is what I'm\n\n917\n00:40:32.900 --> 00:40:33.600\nasking of and\n\n918\n00:40:33.600 --> 00:40:38.190\nexpecting of you. And the thing that I was wanted to do that I debated was I\n\n919\n00:40:38.190 --> 00:40:39.440\nactually wanted to make\n\n920\n00:40:39.440 --> 00:40:44.130\nsure everyone at the company who wanted to be there was there and committed to\n\n921\n00:40:44.130 --> 00:40:45.120\nthis new plan and\n\n922\n00:40:45.120 --> 00:40:49.370\nthis level of effort, and that anyone who was not intending to be there or did\n\n923\n00:40:49.370 --> 00:40:50.240\nnot feel like this\n\n924\n00:40:50.240 --> 00:40:54.520\nwas a good idea for them was out the door. So what I wanted to do was this\n\n925\n00:40:54.520 --> 00:40:55.600\nthing we ended up calling\n\n926\n00:40:55.600 --> 00:41:00.220\nat the graceful leave program, where we offered everyone a severance package\n\n927\n00:41:00.220 --> 00:41:01.040\nafter I had shared\n\n928\n00:41:01.040 --> 00:41:04.030\nthis new strategy and these new expectations and said every single person, if\n\n929\n00:41:04.030 --> 00:41:04.560\nyou don't want to\n\n930\n00:41:04.560 --> 00:41:09.920\nbe part of this, here's a check, here you can go now. But the question for us\n\n931\n00:41:09.920 --> 00:41:11.200\nwas, A, like what is\n\n932\n00:41:11.200 --> 00:41:14.040\nthis going to do? Like, are we going to have 20 people left at the end of this?\n\n933\n00:41:14.040 --> 00:41:14.720\nYou know, who's\n\n934\n00:41:14.720 --> 00:41:18.730\ngoing to stay and who's not? Is this too risky? And also when do we do it?\n\n935\n00:41:18.730 --> 00:41:19.440\nBecause I was two months\n\n936\n00:41:19.440 --> 00:41:22.800\nin and there was a lot of discussion, maybe we should do at the end of Q1 or Q2\n\n937\n00:41:22.800 --> 00:41:24.800\n. Well, it turned out we\n\n938\n00:41:24.800 --> 00:41:28.680\ndid it in February. We executed this plan, we offered people severance. A\n\n939\n00:41:28.680 --> 00:41:29.840\nnumber of people took\n\n940\n00:41:29.840 --> 00:41:33.240\nit. We also, you know, helped coach some people out that maybe we're not a good\n\n941\n00:41:33.240 --> 00:41:34.160\ncultural fit. So it\n\n942\n00:41:34.160 --> 00:41:38.330\nwas a huge actual win for us. But what I realized was the pandemic hit in March\n\n943\n00:41:38.330 --> 00:41:40.240\n. And if we had not\n\n944\n00:41:40.240 --> 00:41:44.040\nmoved fast and executed on that in February, we would have been a very\n\n945\n00:41:44.040 --> 00:41:45.360\ndifferent situation in\n\n946\n00:41:45.360 --> 00:41:48.130\nterms of executing that type of transformation of our workforce and our\n\n947\n00:41:48.130 --> 00:41:49.360\nbusiness during the pandemic.\n\n948\n00:41:49.360 --> 00:41:54.320\nWhen it was like a no-no to fire anybody. So I had debated and deliberated the\n\n949\n00:41:54.320 --> 00:41:54.880\ntime frame.\n\n950\n00:41:54.880 --> 00:41:57.520\nI got some great input from people that were like, hey, we know you want to\n\n951\n00:41:57.520 --> 00:41:58.000\nmove fast,\n\n952\n00:41:58.000 --> 00:42:01.280\njust do it in February. And I did it. And looking back, that was such a good\n\n953\n00:42:01.280 --> 00:42:02.160\ndecision. And that gave\n\n954\n00:42:02.160 --> 00:42:06.160\nme a lot of confidence in future decisions about moving fast, not equivocating,\n\n955\n00:42:06.160 --> 00:42:06.720\nand just going\n\n956\n00:42:06.720 --> 00:42:10.960\nforward, even when the outcome was very much unknown. Yeah. Well, the graceful\n\n957\n00:42:10.960 --> 00:42:11.360\nleave, that's\n\n958\n00:42:11.360 --> 00:42:15.590\nanother, another example of where your clarity really paid off. You said, this\n\n959\n00:42:15.590 --> 00:42:16.720\nis where we're going.\n\n960\n00:42:17.840 --> 00:42:21.690\nYou know, I'm excited about where it is. I think there's huge potential there.\n\n961\n00:42:21.690 --> 00:42:22.720\nBut you got to,\n\n962\n00:42:22.720 --> 00:42:26.070\nyou got to believe it too. And if you believe it, we're together, if not, you\n\n963\n00:42:26.070 --> 00:42:27.920\ncan leave grace.\n\n964\n00:42:27.920 --> 00:42:35.160\nWell, that's a pretty good example. And you mentioned COVID and you became CO\n\n965\n00:42:35.160 --> 00:42:35.600\nright before\n\n966\n00:42:35.600 --> 00:42:42.600\nthe pandemic. How did that accelerate your learning just on remote work? What\n\n967\n00:42:42.600 --> 00:42:44.240\nhave you learned about\n\n968\n00:42:44.240 --> 00:42:49.760\nremote work because of COVID? That's a great question. Because people are of\n\n969\n00:42:49.760 --> 00:42:50.720\nhybrid and remote\n\n970\n00:42:50.720 --> 00:42:54.210\noriented company before COVID, we always had a four one model in our offices,\n\n971\n00:42:54.210 --> 00:42:54.960\nfour days in the\n\n972\n00:42:54.960 --> 00:42:58.860\noffice, one day remote. And then we had this extensive team of freelancers\n\n973\n00:42:58.860 --> 00:42:59.840\npredominantly who\n\n974\n00:42:59.840 --> 00:43:03.410\nare nowhere near our offices. So we had this huge remote workforce. It was easy\n\n975\n00:43:03.410 --> 00:43:04.480\nfor us to flip the\n\n976\n00:43:04.480 --> 00:43:08.160\nswitch and go fully remote when COVID happened. I did learn how hard it was for\n\n977\n00:43:08.160 --> 00:43:09.120\nother companies and\n\n978\n00:43:09.120 --> 00:43:12.210\nhow much we could help and educate them with some of our practices. So that was\n\n979\n00:43:12.210 --> 00:43:12.800\na benefit.\n\n980\n00:43:12.800 --> 00:43:17.980\nBut I also learned, to my comments earlier, remote work when it's fully remote\n\n981\n00:43:17.980 --> 00:43:18.320\nand you can\n\n982\n00:43:18.320 --> 00:43:21.590\nnever get together in person, which was the case more or less for the first one\n\n983\n00:43:21.590 --> 00:43:22.000\nand a half,\n\n984\n00:43:22.000 --> 00:43:25.580\ntwo years of the pandemic, is very different than remote work when you can have\n\n985\n00:43:25.580 --> 00:43:26.240\nthese in-person\n\n986\n00:43:26.240 --> 00:43:29.900\ntouchpoints. And I think one mistake we made during COVID is we grew the\n\n987\n00:43:29.900 --> 00:43:31.120\nbusiness significantly.\n\n988\n00:43:31.120 --> 00:43:35.160\nOur top line nearly doubled or did double our employee base expanded\n\n989\n00:43:35.160 --> 00:43:36.480\nsignificantly as well.\n\n990\n00:43:36.480 --> 00:43:40.240\nBut because we were already so good at remote work, we didn't think about\n\n991\n00:43:40.240 --> 00:43:41.280\naccepting our team\n\n992\n00:43:41.280 --> 00:43:44.640\nmembers that we were hiring with all of the practices, with the level of\n\n993\n00:43:44.640 --> 00:43:45.760\nintentionality\n\n994\n00:43:45.760 --> 00:43:48.280\nthat we had had in the past. Because in the past, people just come in the\n\n995\n00:43:48.280 --> 00:43:49.040\noffice and be\n\n996\n00:43:49.040 --> 00:43:51.840\nremote and they kind of learn these things through the way our culture work,\n\n997\n00:43:51.840 --> 00:43:52.560\nthey be in person,\n\n998\n00:43:52.560 --> 00:43:55.840\nsometimes, etc. Without those in-person touchpoints and without enough\n\n999\n00:43:55.840 --> 00:43:57.120\nintentionality around what\n\n1000\n00:43:57.120 --> 00:44:00.690\nour remote work model was, we actually kind of backslid a period of time where\n\n1001\n00:44:00.690 --> 00:44:01.280\nit was like,\n\n1002\n00:44:01.280 --> 00:44:05.840\noh, this isn't as effective as it could be. So since then, we've really dialed\n\n1003\n00:44:05.840 --> 00:44:06.480\nour dials in\n\n1004\n00:44:06.480 --> 00:44:10.040\nterms of the intentionality, in terms of the communication around what our\n\n1005\n00:44:10.040 --> 00:44:10.960\napproaches are.\n\n1006\n00:44:10.960 --> 00:44:13.890\nBut I think it was definitely interesting to see kind of through that period,\n\n1007\n00:44:13.890 --> 00:44:14.080\nsome of the\n\n1008\n00:44:14.080 --> 00:44:17.030\nstruggles that we ourselves had at moments because of our growth and because\n\n1009\n00:44:17.030 --> 00:44:17.680\npeople didn't all\n\n1010\n00:44:17.680 --> 00:44:21.680\nunderstand how to work in our remote company. And nobody has a crystal ball,\n\n1011\n00:44:21.680 --> 00:44:22.320\nbut if you could\n\n1012\n00:44:22.320 --> 00:44:28.880\nlook out five years from now, how would you describe the remote work world? It\n\n1013\n00:44:28.880 --> 00:44:29.120\n's going to\n\n1014\n00:44:29.120 --> 00:44:33.000\nkeep getting better because the technology will improve. And I do think\n\n1015\n00:44:33.000 --> 00:44:34.320\ntechnology enablement\n\n1016\n00:44:34.320 --> 00:44:38.520\nas a huge driver here of whether remote work is successful or not. So I'm an\n\n1017\n00:44:38.520 --> 00:44:39.360\noptimist in that\n\n1018\n00:44:39.360 --> 00:44:44.080\nsense. I do think though, at this moment, everyone is recognizing the value of\n\n1019\n00:44:44.080 --> 00:44:44.960\nin-person and trying\n\n1020\n00:44:44.960 --> 00:44:48.950\nto find that balance again, having many companies swan extremely remote. And I\n\n1021\n00:44:48.950 --> 00:44:49.440\nthink that's going\n\n1022\n00:44:49.440 --> 00:44:53.000\nto continue. I think we're going to see more of these hybrid models where\n\n1023\n00:44:53.000 --> 00:44:54.560\npeople have a mixed workforce\n\n1024\n00:44:54.560 --> 00:44:58.800\nof onsite and remote folks, but the technology enablement will mean the remote\n\n1025\n00:44:58.800 --> 00:44:59.840\npeople can contribute\n\n1026\n00:44:59.840 --> 00:45:03.280\nand be participating in even higher levels than probably what we see today.\n\n1027\n00:45:03.280 --> 00:45:08.000\nYou know, I've seen technology where it's like, if you and I were sitting right\n\n1028\n00:45:08.000 --> 00:45:08.640\nacross from each\n\n1029\n00:45:08.640 --> 00:45:12.920\nother like we're doing right now, I could basically put my hand into your\n\n1030\n00:45:12.920 --> 00:45:14.160\nscreen. And it's almost\n\n1031\n00:45:14.160 --> 00:45:17.580\nlike we could shake hands. It's like, pick up an apple off your desk or\n\n1032\n00:45:17.580 --> 00:45:18.560\nwhatever. I mean,\n\n1033\n00:45:18.560 --> 00:45:25.920\nit's amazing. You know, where do you see that going? I mean, I am sure these\n\n1034\n00:45:25.920 --> 00:45:26.880\nthings will continue to\n\n1035\n00:45:26.880 --> 00:45:30.860\ncome kind of from the lab, you know, into reality. That is the natural\n\n1036\n00:45:30.860 --> 00:45:32.320\ntechnology lifecycle.\n\n1037\n00:45:32.320 --> 00:45:37.040\nAnd I think it's easy to underestimate how impactful they'll be. I'll give you\n\n1038\n00:45:37.040 --> 00:45:38.480\none example. We, as a\n\n1039\n00:45:38.480 --> 00:45:44.870\nleadership team, decided to adopt kind of we got the like meta 3D glasses and\n\n1040\n00:45:44.870 --> 00:45:46.240\nwe did some of our\n\n1041\n00:45:46.240 --> 00:45:51.330\nteam meetings during the pandemic through like a virtual reality setup. And\n\n1042\n00:45:51.330 --> 00:45:52.240\nmost of it was actually\n\n1043\n00:45:52.240 --> 00:45:55.100\nlike terrible because the technology wasn't very good and there were all kinds\n\n1044\n00:45:55.100 --> 00:45:55.680\nof issues.\n\n1045\n00:45:55.680 --> 00:45:59.920\nBut one thing I remember clearly was the stereoscopic sound where we could kind\n\n1046\n00:45:59.920 --> 00:46:00.400\nof\n\n1047\n00:46:00.400 --> 00:46:04.120\ntalk over and with each other more naturally the way you are in a room versus\n\n1048\n00:46:04.120 --> 00:46:04.880\non zoom where it's\n\n1049\n00:46:04.880 --> 00:46:08.200\nkind of turn by turn talking and then people talk over each other and they both\n\n1050\n00:46:08.200 --> 00:46:09.360\nhave to stop and\n\n1051\n00:46:09.360 --> 00:46:13.870\nit's kind of messy. Just that improvement actually made it feel like such a\n\n1052\n00:46:13.870 --> 00:46:14.400\nbetter,\n\n1053\n00:46:14.400 --> 00:46:18.640\nhigher quality touch point for us as a team. So if you imagine that's just like\n\n1054\n00:46:18.640 --> 00:46:19.200\none small\n\n1055\n00:46:19.200 --> 00:46:23.040\ninnovation that can come to all of our remote work tools and then multiply it\n\n1056\n00:46:23.040 --> 00:46:23.440\ntimes these\n\n1057\n00:46:23.440 --> 00:46:26.560\nmore dramatic things, you know, whether it's kind of hologram type, you know,\n\n1058\n00:46:26.560 --> 00:46:27.360\nin person experiences,\n\n1059\n00:46:27.360 --> 00:46:30.890\nlike the one you're describing, there's a lot there. And again, I think that\n\n1060\n00:46:30.890 --> 00:46:31.760\nthe exponential\n\n1061\n00:46:31.760 --> 00:46:35.400\nimprovement of what remote can be based on that is huge. You know, this has\n\n1062\n00:46:35.400 --> 00:46:36.880\nbeen so much fun and\n\n1063\n00:46:36.880 --> 00:46:39.760\nI want to have some more with my lightning round of questions. Are you ready\n\n1064\n00:46:39.760 --> 00:46:40.320\nfor this?\n\n1065\n00:46:40.320 --> 00:46:45.120\nI'll do my best. I'll do my best. Well, one thing I know is for sure we're\n\n1066\n00:46:45.120 --> 00:46:46.080\ngoing to get some clarity\n\n1067\n00:46:46.080 --> 00:46:50.960\nhere. Okay. But what are the three words that best destroy you? Bold,\n\n1068\n00:46:50.960 --> 00:46:52.720\nanalytical, compassionate.\n\n1069\n00:46:52.720 --> 00:46:56.800\nIf you could be one person for a day beside yourself, who would it be?\n\n1070\n00:46:56.800 --> 00:47:00.800\nI'd want to be one of my kids. I would love to be a child again and experience\n\n1071\n00:47:00.800 --> 00:47:01.280\nchildhood,\n\n1072\n00:47:01.280 --> 00:47:04.600\nyou know, through their eyes and also see what kind of parents they think my\n\n1073\n00:47:04.600 --> 00:47:05.280\nhusband and I are.\n\n1074\n00:47:05.280 --> 00:47:11.120\nWhat's your biggest pet peeve? I have this thing. I'm a stickler for setting\n\n1075\n00:47:11.120 --> 00:47:12.320\ngoals with dates\n\n1076\n00:47:12.320 --> 00:47:17.040\nand then being clear with metrics using a framework called from X to Y by when.\n\n1077\n00:47:17.040 --> 00:47:21.600\nClarity again. Who would play you in a movie?\n\n1078\n00:47:21.600 --> 00:47:24.400\nCan I say Idris Elba? Because he's just so awesome.\n\n1079\n00:47:24.400 --> 00:47:28.720\nPerfect. I love it. You know, how many languages do you speak?\n\n1080\n00:47:28.720 --> 00:47:34.160\n2.2. What's the point to? My Nepali used to be a lot better when we lived in\n\n1081\n00:47:34.160 --> 00:47:35.360\ncommon do and now\n\n1082\n00:47:35.360 --> 00:47:39.290\nit's definitely degraded. And what's your other language besides English?\n\n1083\n00:47:39.290 --> 00:47:40.160\nSpanish. Oh, and I have\n\n1084\n00:47:40.160 --> 00:47:44.270\na bit of Japanese too. So maybe it's 2.5. What's the one thing you do just for\n\n1085\n00:47:44.270 --> 00:47:44.720\nyou?\n\n1086\n00:47:44.720 --> 00:47:48.690\nDry fast with loud music and the windows down. All right. If I turn on the\n\n1087\n00:47:48.690 --> 00:47:49.440\nradio in your car,\n\n1088\n00:47:49.440 --> 00:47:54.000\nwhat would I hear? You would hear Gold Gun Girls, which is like one of my\n\n1089\n00:47:54.000 --> 00:47:55.840\nfavorite songs by metric\n\n1090\n00:47:55.840 --> 00:48:00.130\nand probably some Taylor Swift. I'm still like the man and you've got to calm\n\n1091\n00:48:00.130 --> 00:48:00.960\ndown. There's\n\n1092\n00:48:00.960 --> 00:48:05.200\nsome of my favorites. Besides your family, what's your your most prized\n\n1093\n00:48:05.200 --> 00:48:06.160\npossession?\n\n1094\n00:48:06.160 --> 00:48:11.220\nMaybe my house. We designed that thing to be so purpose- purposeful for what we\n\n1095\n00:48:11.220 --> 00:48:11.760\nwanted.\n\n1096\n00:48:11.760 --> 00:48:15.120\nYeah, that's great. What's something about you a few people would know?\n\n1097\n00:48:15.120 --> 00:48:19.040\nI'm a huge design junkie. Like my close friends know this, but architecture and\n\n1098\n00:48:19.040 --> 00:48:20.320\ninterior design,\n\n1099\n00:48:20.320 --> 00:48:23.920\nthat's like my second life. And what's one of your daily rituals? Something\n\n1100\n00:48:23.920 --> 00:48:25.600\nthat you never ever miss?\n\n1101\n00:48:25.600 --> 00:48:29.950\nSun before screens. I always have to look at the sky before I turn on my phone\n\n1102\n00:48:29.950 --> 00:48:30.720\nin the morning.\n\n1103\n00:48:30.720 --> 00:48:34.240\nOh, that's cool. That's cool. All right. We're out of the lightning round.\n\n1104\n00:48:34.240 --> 00:48:34.880\nGreat job.\n\n1105\n00:48:34.880 --> 00:48:39.040\nAnd I just got a few more questions for you and we'll wrap this up. You know, I\n\n1106\n00:48:39.040 --> 00:48:39.680\n've heard you tell\n\n1107\n00:48:39.680 --> 00:48:44.180\nstories about the adventures your parents would take you on as a kid and you\n\n1108\n00:48:44.180 --> 00:48:45.280\nlived in Nepal and,\n\n1109\n00:48:45.280 --> 00:48:52.080\nyou know, how are you leaning into that same kind of adventure now as a parent?\n\n1110\n00:48:52.080 --> 00:48:56.760\nIt's really important to me that my kids feel like they're part of a world that\n\n1111\n00:48:56.760 --> 00:48:57.440\n's bigger than,\n\n1112\n00:48:57.440 --> 00:49:02.210\nyou know, where we are in California. We do an international trip minimum once\n\n1113\n00:49:02.210 --> 00:49:03.040\na year with them,\n\n1114\n00:49:03.040 --> 00:49:06.860\nso they can kind of see and experience the world. This year I also took my 10-\n\n1115\n00:49:06.860 --> 00:49:07.680\nyear-old to Ecuador\n\n1116\n00:49:07.680 --> 00:49:10.830\nin a one-on-one trip because I wanted her to see that and to have that one-on-\n\n1117\n00:49:10.830 --> 00:49:11.600\none time with her.\n\n1118\n00:49:11.600 --> 00:49:16.360\nSo travel for us is a big thematic where we're constantly getting out and I\n\n1119\n00:49:16.360 --> 00:49:16.960\nwant my kids to have\n\n1120\n00:49:16.960 --> 00:49:20.290\nthat exposure. I'm not ready to be an expat with them yet, but I do want them\n\n1121\n00:49:20.290 --> 00:49:20.960\nto feel like they\n\n1122\n00:49:20.960 --> 00:49:25.650\nreally are global citizens. And what kind of leadership, because you're\n\n1123\n00:49:25.650 --> 00:49:26.880\nobviously an excellent\n\n1124\n00:49:26.880 --> 00:49:31.500\nleader, what kind of leadership do you try to take home with you when you're\n\n1125\n00:49:31.500 --> 00:49:32.000\ndealing with your\n\n1126\n00:49:32.000 --> 00:49:36.800\nhusband and your family? And how do you look at leadership at home? Leadership\n\n1127\n00:49:36.800 --> 00:49:37.600\nat home for me\n\n1128\n00:49:37.600 --> 00:49:42.310\nDavid is all about love. It's all about leading from a place of love. My\n\n1129\n00:49:42.310 --> 00:49:43.200\nbiggest goal as a parent\n\n1130\n00:49:43.200 --> 00:49:48.320\nis for my kids to know they are unconditionally loved. It's not about great, it\n\n1131\n00:49:48.320 --> 00:49:48.720\n's not about\n\n1132\n00:49:48.720 --> 00:49:51.680\nperformance. Nothing is conditional about how much my husband and I love them.\n\n1133\n00:49:51.680 --> 00:49:52.720\nAnd so I'm constantly\n\n1134\n00:49:52.720 --> 00:49:57.110\nfocused on peeling back any layers and just making sure they know how much they\n\n1135\n00:49:57.110 --> 00:49:58.000\nare loved.\n\n1136\n00:49:58.000 --> 00:50:02.070\nAnd you mentioned compassionate is one of the words that you'd use to describe\n\n1137\n00:50:02.070 --> 00:50:03.440\nyourself and\n\n1138\n00:50:03.440 --> 00:50:09.310\ncompassionate being kind. How do you balance that with just the tough-minded\n\n1139\n00:50:09.310 --> 00:50:11.360\nness? It takes to be\n\n1140\n00:50:11.360 --> 00:50:18.080\na CEO like having a graceful leave policy, for example. I mean, that took some\n\n1141\n00:50:18.080 --> 00:50:18.320\ntough\n\n1142\n00:50:18.320 --> 00:50:22.530\nmindedness. Yeah, you know, it can seem like these things are at odds, but I\n\n1143\n00:50:22.530 --> 00:50:23.840\nactually see them as\n\n1144\n00:50:23.840 --> 00:50:27.920\ninterlinked because, you know, in the example of that graceful leave policy,\n\n1145\n00:50:27.920 --> 00:50:30.240\nyes, we invited and\n\n1146\n00:50:30.240 --> 00:50:33.280\nasked some people to leave the business at that time because we knew they weren\n\n1147\n00:50:33.280 --> 00:50:33.920\n't a right fit or\n\n1148\n00:50:33.920 --> 00:50:37.390\nwe wanted them to self-select and we wanted the existing people to like really\n\n1149\n00:50:37.390 --> 00:50:37.760\nopt in.\n\n1150\n00:50:37.760 --> 00:50:41.660\nBut that's a compassionate thing to do to give people choice and to give them\n\n1151\n00:50:41.660 --> 00:50:42.720\nagency and acknowledge\n\n1152\n00:50:42.720 --> 00:50:45.920\nthat they have that agency and acknowledge that if they're not the right fit,\n\n1153\n00:50:45.920 --> 00:50:47.120\nthis is not going to\n\n1154\n00:50:47.120 --> 00:50:50.970\nend well for them or for us anyway, even if we play it out a little bit longer.\n\n1155\n00:50:50.970 --> 00:50:52.000\nSo I think a lot of\n\n1156\n00:50:52.000 --> 00:50:56.480\nthese choices on the face can seem like they're not coming from a place of care\n\n1157\n00:50:56.480 --> 00:50:57.200\nand kindness, but\n\n1158\n00:50:57.200 --> 00:51:01.120\nyou know, one thing I love is like letting people be free to go find greater\n\n1159\n00:51:01.120 --> 00:51:01.840\nopportunities somewhere\n\n1160\n00:51:01.840 --> 00:51:05.440\nelse if they're not a fit here. And that actually is an act of love. Hey,\n\n1161\n00:51:05.440 --> 00:51:06.880\nlisten, every great company\n\n1162\n00:51:06.880 --> 00:51:11.120\nhas a Dorf star. You know, there's something that it's a noble cause. You know,\n\n1163\n00:51:11.120 --> 00:51:12.240\nyou go to work and\n\n1164\n00:51:12.240 --> 00:51:16.070\nyou're just, you're not just going to work to make a paycheck, you're going to\n\n1165\n00:51:16.070 --> 00:51:16.880\nwork to really make\n\n1166\n00:51:16.880 --> 00:51:23.220\nthe world a better place. What's your purpose, Hayden, and how do you drive it\n\n1167\n00:51:23.220 --> 00:51:24.160\ndeep in your\n\n1168\n00:51:24.160 --> 00:51:30.080\norganization? We're very fortunate because we as a business have a purpose that\n\n1169\n00:51:30.080 --> 00:51:30.400\nis so\n\n1170\n00:51:30.400 --> 00:51:35.950\nevident in everything we do. Our purpose is to create opportunity in every era\n\n1171\n00:51:35.950 --> 00:51:37.040\nof work. You know,\n\n1172\n00:51:37.040 --> 00:51:41.520\nwe've done this for businesses and talent through the advent of, you know,\n\n1173\n00:51:41.520 --> 00:51:42.560\nmobile, shifting to the\n\n1174\n00:51:42.560 --> 00:51:46.170\ncloud, social media, like all of these phases of work that have happened over\n\n1175\n00:51:46.170 --> 00:51:47.200\nthe last 20 years,\n\n1176\n00:51:47.200 --> 00:51:51.470\nwe've been right there helping our customers transform and meet those moments.\n\n1177\n00:51:51.470 --> 00:51:52.000\nSo for us,\n\n1178\n00:51:52.000 --> 00:51:57.260\nthat purpose around creating opportunity in every era of work continues to be\n\n1179\n00:51:57.260 --> 00:51:59.120\nfresh and relevant\n\n1180\n00:51:59.120 --> 00:52:03.200\nbecause work is constantly changing. And there's always more we can do to make\n\n1181\n00:52:03.200 --> 00:52:04.640\nwork better for all\n\n1182\n00:52:04.640 --> 00:52:07.290\nthe participants in it, which is like it's a huge mission statement if you\n\n1183\n00:52:07.290 --> 00:52:08.720\nthink about it that way.\n\n1184\n00:52:08.720 --> 00:52:13.270\nSo we have this purpose, we drive it through, I mean, we show it in every all\n\n1185\n00:52:13.270 --> 00:52:13.920\nhands, we talk\n\n1186\n00:52:13.920 --> 00:52:17.070\nabout it in every weekly meeting, how the work we're doing connects back to\n\n1187\n00:52:17.070 --> 00:52:17.920\nthat purpose. And\n\n1188\n00:52:17.920 --> 00:52:22.000\none of the ways it becomes very vivid is through customer stories and bringing\n\n1189\n00:52:22.000 --> 00:52:22.720\ncustomers in\n\n1190\n00:52:22.720 --> 00:52:27.490\nthrough video, through live interviews, etc. to talk about how that purpose has\n\n1191\n00:52:27.490 --> 00:52:28.480\nimpacted them\n\n1192\n00:52:28.480 --> 00:52:32.640\ndirectly. And I think that is one of the things that energizes us all the most.\n\n1193\n00:52:32.640 --> 00:52:38.560\nYou know, we started out this conversation by talking about dating sites and\n\n1194\n00:52:38.560 --> 00:52:39.360\nwhat you'd learned\n\n1195\n00:52:39.360 --> 00:52:45.040\nthat you could apply to the Upwork. And I'm actually interviewing tomorrow\n\n1196\n00:52:45.040 --> 00:52:46.320\nWhitney Wolf-Hurd,\n\n1197\n00:52:46.320 --> 00:52:52.400\nthe head of Bumble. What question would you like to ask her if you could?\n\n1198\n00:52:52.400 --> 00:52:57.520\nIt seems like on the precipice of AI, you know, a lot of the kind of prior\n\n1199\n00:52:57.520 --> 00:52:58.880\nmodels around dating and\n\n1200\n00:52:58.880 --> 00:53:03.780\neven companionship are changing in terms of both the tools that can be used to\n\n1201\n00:53:03.780 --> 00:53:05.280\nkind of facilitate\n\n1202\n00:53:05.280 --> 00:53:10.460\nmatches and people actually looking for things from AI tools in terms of, you\n\n1203\n00:53:10.460 --> 00:53:11.760\nknow, relationships\n\n1204\n00:53:11.760 --> 00:53:15.070\nthat they didn't even think about before we wouldn't even have thought about in\n\n1205\n00:53:15.070 --> 00:53:15.680\nthe past.\n\n1206\n00:53:15.680 --> 00:53:19.470\nSo I'm really curious to understand how is she seeing her business not just in\n\n1207\n00:53:19.470 --> 00:53:20.000\nthe next year\n\n1208\n00:53:20.000 --> 00:53:23.100\nto change by AI, but what does it look like in five years? I think that would\n\n1209\n00:53:23.100 --> 00:53:23.680\nbe an interesting\n\n1210\n00:53:23.680 --> 00:53:28.560\nprognostication. I agree. I'll definitely ask you that. And in thinking about\n\n1211\n00:53:28.560 --> 00:53:29.120\nthe future,\n\n1212\n00:53:29.120 --> 00:53:33.960\nwhat do you see as your unfinished business? I mean, Upwork feels like very\n\n1213\n00:53:33.960 --> 00:53:34.800\nunfinished business\n\n1214\n00:53:34.800 --> 00:53:38.240\nfor me. I mean, we are at the beginning of unlocking a huge market and really\n\n1215\n00:53:38.240 --> 00:53:39.280\nchanging work for so\n\n1216\n00:53:39.280 --> 00:53:43.270\nmany more people. So this is like an incredible privilege and joy to work on\n\n1217\n00:53:43.270 --> 00:53:44.480\nthis very unfinished\n\n1218\n00:53:44.480 --> 00:53:49.320\nbusiness. And what's one piece of advice you'd give to anyone who wants to be a\n\n1219\n00:53:49.320 --> 00:53:50.160\nbetter leader?\n\n1220\n00:53:50.160 --> 00:53:55.820\nYou know, I think people see bold moves as somehow hard and they hold\n\n1221\n00:53:55.820 --> 00:53:57.360\nthemselves back because they\n\n1222\n00:53:57.360 --> 00:54:03.490\nwant to find some path that maybe doesn't seem as disruptive. But the clarity\n\n1223\n00:54:03.490 --> 00:54:04.720\nand the boldness\n\n1224\n00:54:04.720 --> 00:54:07.840\nand really facing like, what's the worst that could happen? We asked ourselves\n\n1225\n00:54:07.840 --> 00:54:08.320\nwhen we did this\n\n1226\n00:54:08.320 --> 00:54:10.660\ngraceful leave. What's the worst that could happen? And we said, you know, we'd\n\n1227\n00:54:10.660 --> 00:54:11.440\nrather be\n\n1228\n00:54:11.440 --> 00:54:15.280\na tiny team of highly committed people than a big team of medium or not\n\n1229\n00:54:15.280 --> 00:54:16.800\ncommitted people.\n\n1230\n00:54:16.800 --> 00:54:20.240\nAnd I think asking yourself, what's the worst that can happen can really unlock\n\n1231\n00:54:20.240 --> 00:54:20.720\nfor you as a\n\n1232\n00:54:20.720 --> 00:54:24.190\nleader willingness to do these things that on the face of it may be seem bold\n\n1233\n00:54:24.190 --> 00:54:25.120\nor hard. But once\n\n1234\n00:54:25.120 --> 00:54:28.380\nyou think it through, it's like the obvious thing you would do. Well, I can\n\n1235\n00:54:28.380 --> 00:54:29.440\ntell you, the best thing\n\n1236\n00:54:29.440 --> 00:54:33.580\nthat happened to me today is this conversation. You know, you are a tremendous\n\n1237\n00:54:33.580 --> 00:54:34.720\nleader. I'm so\n\n1238\n00:54:34.720 --> 00:54:39.440\nexcited that people will get to learn from your insights and and be able to\n\n1239\n00:54:39.440 --> 00:54:40.880\nhopefully up their\n\n1240\n00:54:40.880 --> 00:54:44.890\ngame like you have continually throughout your career. And and I wish you all\n\n1241\n00:54:44.890 --> 00:54:45.440\nthe best.\n\n1242\n00:54:45.440 --> 00:54:47.920\nThank you so much, David. This is a lot of fun.\n\n1243\n00:54:47.920 --> 00:54:58.950\nIt's probably easy to categorize clarity is just one more leadership skill you\n\n1244\n00:54:58.950 --> 00:54:59.600\nhave to have.\n\n1245\n00:54:59.600 --> 00:55:06.240\nBut Hayden shows us it's one of the most important tools a leader has. Without\n\n1246\n00:55:06.240 --> 00:55:06.480\nit,\n\n1247\n00:55:06.480 --> 00:55:10.800\nyour team will miss opportunities and be less efficient. But to give your team\n\n1248\n00:55:10.800 --> 00:55:11.440\nclarity,\n\n1249\n00:55:11.440 --> 00:55:15.840\nyou need more than good communication skills. You need curiosity to truly\n\n1250\n00:55:15.840 --> 00:55:16.960\nunderstand challenges\n\n1251\n00:55:16.960 --> 00:55:21.840\nthey're facing. You need courage to step into tough conversations. And you got\n\n1252\n00:55:21.840 --> 00:55:22.560\nto be willing to\n\n1253\n00:55:22.560 --> 00:55:26.720\nmake bold decisions, especially when no one else is quite sure what to do.\n\n1254\n00:55:26.720 --> 00:55:28.880\nHayden models that so\n\n1255\n00:55:28.880 --> 00:55:33.400\nwell, and it's a big reason Upwork is able to succeed in a world that's moving\n\n1256\n00:55:33.400 --> 00:55:34.480\nfaster than ever.\n\n1257\n00:55:35.040 --> 00:55:39.690\nSo here's your challenge this week. Find one way you can clear up a situation\n\n1258\n00:55:39.690 --> 00:55:40.880\nfor your team.\n\n1259\n00:55:40.880 --> 00:55:45.920\nMaybe it's a conflict that's been festering, a product that's been stalling, or\n\n1260\n00:55:45.920 --> 00:55:46.960\na big decision\n\n1261\n00:55:46.960 --> 00:55:52.810\nthat needs to be made, but there's confusion all around it. Step in and lead,\n\n1262\n00:55:52.810 --> 00:55:54.400\nbring the curiosity\n\n1263\n00:55:54.400 --> 00:55:58.530\nand courage. I know that you've got and give your people the clarity they need\n\n1264\n00:55:58.530 --> 00:55:59.600\nto move forward.\n\n1265\n00:56:00.240 --> 00:56:03.610\nSo do you want to know how leaders lead? What we learned today is the great\n\n1266\n00:56:03.610 --> 00:56:04.560\nleaders create\n\n1267\n00:56:04.560 --> 00:56:10.120\nclarity for their teams. Coming up next on how leaders lead is Klaus Kleinfeld,\n\n1268\n00:56:10.120 --> 00:56:11.280\nformer CEO of\n\n1269\n00:56:11.280 --> 00:56:16.310\nSiemens and Alcoa. So be sure you subscribe on YouTube or wherever you get your\n\n1270\n00:56:16.310 --> 00:56:17.600\npodcasts so you\n\n1271\n00:56:17.600 --> 00:56:22.180\ndon't miss it. Thanks again for tuning in to another episode of how leaders\n\n1272\n00:56:22.180 --> 00:56:23.040\nlead where every\n\n1273\n00:56:23.040 --> 00:56:27.130\nThursday you get to listen in while I interview some of the very best leaders\n\n1274\n00:56:27.130 --> 00:56:28.080\nin the world.\n\n1275\n00:56:28.080 --> 00:56:32.180\nI make it a point to give you something simple on each episode that you can\n\n1276\n00:56:32.180 --> 00:56:33.840\napply to your business\n\n1277\n00:56:33.840 --> 00:56:37.440\nso that you will become the best leader you can be.\n","is_pinned",false,"pinned_at","is_featured","featured_at","mix_url","https://chtbl.com/track/DCB44F/traffic.megaphone.fm/DVL3368310861.mp3","dx_media_id",2475,"video_media_id","thumbnail_image_media_id","published_date","2025-09-11","itunes_episode_id",256,"youtube_id","kPGA3XCiG08","2025-09-11T15:46:57.000000Z","dx_url","https://dnl.nyc3.cdn.digitaloceanspaces.com/uploads/6SUmioJdm68fOf4xAd4EtA5XLfDOm6lF9KjfLDdz.mp3","dx_filename","6SUmioJdm68fOf4xAd4EtA5XLfDOm6lF9KjfLDdz.mp3","dx_mux_playback_id","yjk7xh44RjnoPdzsPzrHx02YZOfs8uwvA6yUM013h6SFw","dx_waveform_url","https://dnl.nyc3.cdn.digitaloceanspaces.com/uploads/waveforms/2475.json","video_url","video_mux_playback_id","duration",3396641,"thumbnail_url","https://img.youtube.com/vi/kPGA3XCiG08/maxresdefault.jpg","thumbnail_image_url","dx_media",{"_13":66,"_95":79,"_96":77,"_97":-5,"_31":81,"_33":98,"_99":-5,"_100":83,"_86":87,"_101":-5},"video_media","thumbnail_image_media","filename","url","status","PAeaX7PgpJi9fOdGWRDwmYOrPmf915c4TnqtHOyrtFo","mux_upload_id","waveform_url","preview_media_id","first_name","Hayden","last_name","Brown","job_title","Upwork, CEO","Hayden Brown, woman, female, CEO, Upwork, technology","external_links","https://www.linkedin.com/in/haydenlbrown,https://www.upwork.com/about/team,https://x.com/hydnbrwn/",0,1,"image_media_id",2473,2474,"2026-07-28T18:09:46.000000Z","send_push_notification_at","image_url","https://dnl.nyc3.cdn.digitaloceanspaces.com/uploads/U80Q6cEML1aHCYnes5h0WIg2AFT37k056ruWl2c4.jpg","https://dnl.nyc3.cdn.digitaloceanspaces.com/uploads/IKzIkOBVheIOoXc9yAbX6SFFILMZYnKGTRao2Qks.jpg","https://www.howleaderslead.com/leaders/244/hayden-brown","industry_id",2,"industry",{"_13":123,"_134":135,"_136":138},"industries",[133],"image_media",{"_13":114,"_95":132,"_96":119,"_97":-5,"_31":-5,"_33":-5,"_99":-5,"_100":-5,"_86":-5,"_101":-5},{"_13":115,"_95":131,"_96":120,"_97":-5,"_31":-5,"_33":-5,"_99":-5,"_100":-5,"_86":-5,"_101":-5},"IKzIkOBVheIOoXc9yAbX6SFFILMZYnKGTRao2Qks.jpg","U80Q6cEML1aHCYnes5h0WIg2AFT37k056ruWl2c4.jpg",{"_13":123,"_134":135,"_136":137},"name","Technology","pivot",{"_35":36,"_122":123},{"_35":36,"_122":123},"user","token","favorites",[],"collections",[],"env",{"_147":148,"_149":150,"_151":152,"_153":154,"_155":156},"GOOGLE_CLIENT_ID","644017954836-qpllhu38r0tsrtfq85ukntcvsb0akbht.apps.googleusercontent.com","APPLE_CLIENT_ID","com.howleaderslead.webapp","APPLE_REDIRECT_URI","https://www.howleaderslead.com/auth/apple-callback","APP_URL","https://howleaderslead.com","GTM_ID",""]