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How Leaders Lead with David Novak

#256: Hayden Brown, CEO of Upwork – Create clarity for your team

How Leaders Lead with David Novak

David Novak Leadership

Entrepreneurship, Business, Management

4.8596 Ratings

🗓️ 11 September 2025

⏱️ 57 minutes

🧾️ Download transcript

Summary

GUEST: Hayden Brown, CEO of the global freelance marketplace Upwork LISTEN FOR: Insights on AI, remote work, and what it really takes to lead with clarity (and why it’s not what you think) Take your learning further. Get proven leadership advice from these (free!) resources: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠The How Leaders Lead App⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: A vast library of 90-second leadership lessons to stay sharp on the go  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Daily Insight Emails⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: One small (but powerful!) leadership principle to focus on each day Whichever you choose, you can be sure you’ll get the trusted leadership advice you need to advance your career, develop your team, and grow your business.

Transcript

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0:00.0

As a leader, we have to start with a clear and shared narrative of what's the market and what's our situation in the market and what's the problem to be solved or the job to be done.

0:09.7

If we don't know what problem we're solving or we don't know who we're solving it for, we can do all these other steps and they will not move the needle on our ultimate goals.

0:17.3

If you've ever felt like your team is working harder than ever, but not really getting anywhere,

0:22.0

it might not be an effort problem. It might be a clarity problem. Welcome to how leaders lead. I'm

0:28.1

David Nobeck. And every week, I have conversations with the very best leaders in the world to help you

0:33.2

become the best leader you can be. My guest today is Hayden Brown, the CEO of Upwork. Now, if you

0:39.8

aren't familiar with Upwork, they help companies find and hire top freelance talent. And leading in

0:46.0

that space, Hayden has real expertise on two topics every leader is talking about right now,

0:53.5

remote work and AI. You'll hear her insights on both,

0:57.9

and they're terrific, but I also want you to listen to Al Hayden creates clarity for her team.

1:02.8

If you want to cut down on confusion and give your team more direction and confidence,

1:07.4

you're in the right place. Here's my conversation with my good friend and soon to be

1:12.3

yours, Hayden Brown. Now, I understand that you have actually learned a lot about how to run your

1:24.0

business by studying dating sites. You know, tell me about that. You know, a big function of what we do

1:31.2

at Upwork is, you know, connecting businesses from the Fortune 100, you know, companies like Microsoft,

1:37.5

Airbnb, Cloudflare, all the way down to your local mom and pop company. We connect them with the most

1:43.9

in-demand talent in the world. And of course,

1:46.3

that's a large part of matchmaking. That's really where we're kind of finding the exact match for not

1:50.8

just the company, but the hiring manager, the project, the specific issue that they're trying to

1:55.4

solve and going into our tremendous talent pool to find that person. So there are a lot of analogies to dating sites and

2:02.2

kind of matchmaking services generally. And certainly we always try to pull from the best to figure out

2:05.9

how we do that matching better and better every day for our customers. What do you think it's been

...

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