How Leaders Lead with David Novak #256: Hayden Brown, CEO of Upwork – Create clarity for your team
22 snips
Sep 11, 2025 
Hayden Brown, CEO of Upwork, shares her insights on leading remote teams and embracing clarity in communication. She emphasizes the importance of defining vision and priorities, especially in a fast-changing world. Hayden discusses building strong remote teams and integrating AI into workflows. Drawing from personal experiences, she highlights the challenges female leaders face and stresses the need for self-advocacy. With practical strategies for team agility and innovation, her perspective is invaluable for today’s leaders navigating the complexities of modern work.
AI Snips
Chapters
Books
Transcript
Episode notes
From Product Manager To CEO
- Hayden transitioned from strategy/M&A into product management at Upwork and then rose to CEO over a decade.
- Product work taught her to connect deep customer understanding with analytical execution and creative design.
Decision To Suspend Russia Operations
- During the Ukraine war Hayden decided to suspend operations in Russia and Belarus despite internal and customer debate.
- That agonizing decision taught her the loneliness and responsibility inherent to top leadership.
Stop Waiting—Apply Before You Feel Perfectly Ready
- If you want the next role, apply now rather than waiting to 'be more ready'; take the leap and learn on the job.
- Hayden notes many women delay promotions by over-preparing; act sooner to accelerate your career.
