Hayden Brown
Upwork, CEO
Create clarity for your team
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
More from Hayden Brown
Build (and break!) fearlessly
Innovation takes courage. If you want to create something new, be willing to challenge the status quo—even within your own team.
Not every role needs a full-time hire
Work doesn’t have to be organized by headcount. Get clear on the outcomes you need, then bring in the right mix of full-time and freelance talent to achieve them.
Let people see the real you, so they don't default to cheap stereotypes
If you don’t define who you are, people will do it for you. Be open and authentic, and don't leave any room for lazy assumptions.
Even top leaders are still figuring stuff out
There’s no magical point in your career where you “figure it all out.” Whether you’re experienced or just starting out, keep asking questions, learning, and evolving.
Two essentials to make remote teams successful
Remote teams can still have a strong culture. It just takes a little more intention – like prioritizing regular in-person time and setting clear communication practices.
Clarity is your most powerful tool
Before you do anything else, get clear on the problem you’re working on. Without that shared understanding, you won’t make much progress toward solving it.
Clips
| Clip | Leader | Duration |
|---|---|---|
| Even top leaders are still figuring stuff out | Hayden Brown | 1:08 |
| Your culture shapes whether people stay or leave | Hayden Brown | 1:09 |
| Build (and break!) fearlessly | Hayden Brown | 0:54 |
| Clarity is your most powerful tool | Hayden Brown | 0:56 |
| Let people see the real you, so they don't default to cheap stereotypes | Hayden Brown | 0:53 |
| Not every role needs a full-time hire | Hayden Brown | 1:07 |
| Two essentials to make remote teams successful | Hayden Brown | 1:27 |
| How to manage conflict on remote teams | Hayden Brown | 1:14 |
| Ask what’s the worst that can happen | Hayden Brown | 0:36 |
| You’re more ready than you think you are | Hayden Brown | 0:38 |