How Leaders Lead with David Novak #256: Hayden Brown, CEO of Upwork – Create clarity for your team
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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.
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Limousine For Her Brother
- At six, Hayden funded a surprise limo for her brother by collecting thousands of cans and bottles for five cents each.
- That early entrepreneurship taught her the power of earned money to create meaningful impact for others.
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.
Clarity As Leadership's First Duty
- Clarity is the foundational leadership responsibility: define the market, the problem, and the vision before acting.
- Hayden argues that without shared clarity, effort will not move the needle on core goals.
