Podcast Summary

Podcast: How Leaders Lead with David Novak
Episode #256: Hayden Brown, CEO of Upwork – Create clarity for your team
Date: September 11, 2025
Host: David Novak
Guest: Hayden Brown

Episode Overview

This episode features Hayden Brown, CEO of Upwork, as she joins David Novak for a deep dive into how leaders can create clarity for their teams—especially in fast-evolving fields shaped by remote work and AI. Hayden discusses her journey, the lessons learned across consulting, tech, and Upwork, and her philosophy on building effective, purpose-driven organizations. Essential themes include decision-making, company culture, navigating remote work, embracing AI, and championing female leadership. Throughout, Hayden spotlights the need for leaders to boldly define reality and communicate with transparency—demonstrating clarity as a non-negotiable leadership skill.

Key Discussion Points & Insights

Upwork’s Origins and “Matchmaking” Mindset

• Dating site analogy: Upwork is like a dating site for talent—where every hire is unique and matchmaking is critical.
  • "Unlike E-commerce where someone can come into a website and... order that same product..., in the world of Upwork, every person is unique." (Hayden Brown, 02:14)
• Company evolution: Originally founded as oDesk to connect remote talent securely, merged with Elance to become Upwork in 2015, and now pivots rapidly alongside AI advances.

Leadership Shaped by Life Experience

• Entrepreneurial childhood: Motivated by her brother’s illness, Hayden learned early the joy of entrepreneurship tied to meaningful impact.
• Global perspective: Living in Nepal as a child gave her a profound appreciation for privilege and a global sense of purpose.
  • "As Americans, we are so privileged and we have so much access and things that we just take for granted." (Hayden Brown, 06:36)

Building and Transforming Culture

• Lessons from Microsoft: Culture trumps all—the right small team can outshine the broader organization.
• Upwork’s core value:
  • “Build and break fearlessly” is the animating value that underpins innovation and willingness to challenge the status quo.
    • "We need to be fearless every day examining what needs to change... how do we build and break our own culture or our own ways of working..." (Hayden Brown, 10:44)
• Real-world example: Launching "Lifted," a new unit merging acquisitions and internal teams, required breaking and reshaping Upwork’s operating model for better customer service.

From Product Manager to CEO

• Product at Upwork: The bridge between customer empathy, analytics, and creativity. Feedback loops and deep customer engagement remain central.
• Broadening company offerings: As client needs evolved, Upwork naturally expanded across 130+ categories.

Competing and Leading

• Distinct positioning: Upwork’s focus is on complex, relationship-based project work, not just gig tasks—differentiating from competitors like Fiverr.
• Customer-centric innovation: Active customer councils and regular engagement drive incremental and visionary changes, especially with AI.

The Essence of Leadership: Clarity

• Defining and communicating reality: The most vital leadership trait is clarity—diagnosing the challenge, clarifying the market and problem, setting a vision, and freely communicating it.
  • "If we don't know what problem we're solving or who we're solving it for, we can do all these other steps and they will not move the needle." (Hayden Brown, 00:00 / 17:57)
• Giving clarity in complexity:
  • Example: Early bold pivot to AI in 2023, carving out a team to reimagine Upwork with an AI foundation while retaining current priorities.
  • Personal courage to move fast forged under crisis (Ukraine war, Russia/Belarus withdrawal).
    • "I learned and felt that adage that it's lonely at the top... there was no one who could tell me... what really needed to happen." (Hayden Brown, 21:05)

Embracing AI: Personal and Organizational Growth

• Learning by doing: Hayden models AI usage, experiments with tools, and ensures leaders champion by example.
  • "No one in my company is going to believe I'm serious about AI unless I'm showing up, using these tools." (24:30)
• Culture change: Overcoming skepticism and ensuring the whole organization "gets on the bus"—amplified by repeat communication, training, and showcasing wins.

Female Leadership: Wisdom & Challenges

• Overcoming stereotypes:
  • "As the CEO, I've really realized... in our culture there's kind of two types of women leaders who are stereotyped... I am neither of those things." (27:45)
• Advice for women: Don’t hold yourself back—take risks, don’t wait for perfection.
  • "If you're thinking about going, doing that thing, don't do the three things first, like go do that thing." (29:19)

Workforce Strategies: Full-Time vs Freelance

• Workforce composition: Upwork has always operated with a majority freelance/hybrid staff.
  • The paradigm shift: Leaders should think in terms of "skills/projects" not just FTEs.
    • "In the past, most leaders have thought, oh, I hire or I do work with the unit of the FTE... The shift... is to say these aren't FTE units now. It's skills or projects or efforts." (Hayden Brown, 30:28)
• Scoping work: Always start by asking why something can't be done with freelancers.

Remote Work & Building Distributed Culture

• Key practices:
  • Cadence of in-person relationship building alongside remote flexibility.
  • Cameras-on in meetings, transparent communication, strong weekly culture touchpoints.
    • "Remote teams have to have a lot of in person touch points. It can vary... but that's a key part of relationship building." (Hayden Brown, 33:39)
• Managing conflict remotely:
  • Build psychological safety through in-person and social connection, quickly resolve conflicts using any medium, and never let issues fester.

Personal Growth & Overcoming Doubt

• Bold decisions: "Graceful leave" program—offering severance to those not committed, reinforced value of moving fast and acting boldly.
  • "We executed this plan... what I realized was the pandemic hit in March... if we had not moved fast and execute on that in February, we would have been in a very different situation..." (40:01)
• Learning during COVID: Importance of intentional onboarding and maintaining remote work best practices during hypergrowth.

Looking Forward:

• Future of remote work: Increased technology enablement, more hybrid models, and ever-stronger participation from remote teammates.
• Tech trends: Early experiments with VR/AR meetings suggest even small innovations (like better audio) can transform remote collaboration.

Memorable Quotes & Moments

| Timestamp | Quote | Speaker | |-----------|-------|---------| | 00:00 | "If we don't know what problem we're solving or who we're solving it for, we can do all these other steps and they will not move the needle on our ultimate goals." | Hayden Brown | | 06:36 | "As Americans, we are so privileged and we have so much access and things that we just take for granted." | Hayden Brown | | 10:44 | "We need to be fearless every day examining what needs to change... how do we need to build and break our own culture or our own ways of working..." | Hayden Brown | | 17:57 | "Clarity is probably the most important thing. If I look back and at every step of the way, I really focused on bringing clarity to hard problems..." | Hayden Brown | | 21:05 | "I learned and felt that adage that it's lonely at the top... there was no one who could tell me... what really needed to happen." | Hayden Brown | | 24:30 | "No one in my company is going to believe that I'm serious about AI unless I'm showing up, using these tools..." | Hayden Brown | | 27:45 | "As the CEO, I've really realized... in our culture there's kind of two types of women leaders who are stereotyped... I am neither of those things." | Hayden Brown | | 30:28 | "The shift for leaders is to say these aren't FTE units now. It's skills or projects or efforts." | Hayden Brown | | 33:39 | "Remote teams have to have a lot of in person touch points. It can vary... but that's a key part of relationship building." | Hayden Brown | | 40:01 | "We executed this plan... if we had not moved fast and executed that in February, we would have been in a very different situation..." | Hayden Brown | | 51:25 | "Our purpose is to create opportunity in every era of work." | Hayden Brown | | 53:50 | "What's the worst that can happen? Can really unlock for you as a leader willingness to do these things that, on the face of it, maybe seem bold or hard..." | Hayden Brown |

Timestamps for Key Segments

• 00:00-02:14 — The importance of clarity for teams; Upwork’s matchmaking and the dating site analogy
• 04:22-07:38 — Childhood, entrepreneurship, and lessons from Nepal
• 09:25-10:44 — Culture at Microsoft and shaping Upwork’s culture
• 10:44-12:35 — “Build and break fearlessly” and internal transformation
• 17:57-19:04 — The crucial role of clarity in leadership
• 19:04-21:05 — Defining clarity during the AI pivot and the Ukraine crisis
• 24:30-26:43 — Hayden’s personal AI learning and driving organizational adoption
• 27:45-29:57 — Navigating stereotypes and advice for female leaders
• 30:28-33:39 — Balancing freelancers and FTEs with new work paradigms
• 33:39-35:09 — Building remote culture: in-person and virtual best practices
• 37:25-38:31 — Managing conflict in distributed teams
• 40:01-42:09 — Making bold decisions: the “graceful leave” initiative
• 44:28-45:23 — The future of remote work and emerging technologies
• 51:25-52:32 — Upwork’s North Star and organizational purpose
• 53:50-54:27 — The power of bold moves and advice for aspiring leaders
• 46:41-49:58 — Lightning round: personal habits, values, and life outside work

Conclusion & Takeaways

David Novak highlights that clarity is more than a communication skill—it’s fundamental to leadership efficacy. Hayden Brown exemplifies this by defining reality for her teams, making bold decisions, and innovating across technology and culture. Listeners are urged to bring clarity to a challenge in their own work and to lead courageously, confronting ambiguity to help their teams thrive.

Next episode: Klaus Kleinfeld, former CEO of Siemens and Alcoa. Subscribe for more exclusive leadership discussions.