Heather Dunn
Chief People Officer
Brex
Episode 219
Agile HR: The Secret to Cultivating Leaders Who 'Operate at All Levels'
Current chapter: Heather is the head of people at Brex. com
Built By PeopleApril 24, 2025 · 14:12
Thesis
“Effective HR leadership in dynamic environments requires a proactive approach that balances strategic vision with hands-on execution, deeply understands business and customer needs, and employs targeted talent management to drive organizational success and cultural alignment.”
Show notes
Navigating HR Leadership in Startups with Heather Dunn
In this episode of the Built by People Podcast, host Dave welcomes Heather, Chief People Officer at Brex, to discuss her extensive career in human resources, from her beginnings at a claims department to leadership roles at Microsoft, Dropbox, and various startups.
Heather touches on navigating return-to-office mandates while balancing flexibility at Brex, cultivating leaders who can switch between strategy and execution, and refining systems to spot and retain top talent.
She also offers insights on creating an effective 30, 60, 90-day onboarding plan, interviewing prospective employers for fit, and her advice on thriving in the HR function.
00:00 Introduction and Career Journey
01:36 Navigating Return to Office (RTO) and Culture at Brex
04:03 Brex 3.0: Leadership and Management
06:39 Selecting and Retaining Top Talent
08:51 Onboarding as a New Chief People Officer
11:46 Reverse Interviewing for Organizational Fit
13:35 Parting Advice and Conclusion
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What you'll take away
- 1Implement Return-to-Office (RTO) with transparency, clear communication, and embedded flexibility (e.g., 2 days/week, extended work-from-anywhere for new parents) to balance connection with employee needs.
- 2Cultivate leaders who 'operate at all levels' by requiring them to set strategy and perform hands-on execution, fostering respect and trust within their teams.
- 3Develop a targeted 'top talent' program (e.g., for 5% of the organization) with objective criteria, personalized growth options, and highly retentive incentives to significantly boost engagement and retention.
- 4For new CPOs, prioritize a proactive 30-60-90 day plan: Month 1 for internal listening (200+ employees), Month 2 for external business and customer understanding, and Month 3 for setting a data-driven vision and strategy.
- 5As a senior leader, conduct 'reverse interviews' by asking CEOs tough, scenario-based questions and observing leadership team dynamics to ensure fundamental values alignment before accepting a role.
What most organizations get wrong
- •Challenging the CEO's view that 'return to office' would be a 'quick win,' instead framing it as a difficult journey requiring extensive change management and transparency.
- •Eliminating an entire layer of management in 'Brex 3.0' to foster more inspiring, hands-on leadership, directly counter to typical organizational growth patterns.
- •Focusing retention efforts on a 'smaller population' (e.g., 5%) of top talent rather than attempting to apply the same retention strategies across the entire organization.
- •Advising new CPOs to come in with an opinionated 30-60-90 day plan rather than passively waiting for one to be provided by their CEO.
- •Advocating for intentionally asking CEOs 'very difficult questions' during reverse interviews to uncover potential values misalignment, even if it means walking away from a promising opportunity.
In Heather's words
“Someone asked me one day if I wanted to work in personnel. I was working in a claims department and they said,, you know, do you wanna get outta here? And I said, yes, I don't know what personnel is, but sure.”
This quote highlights an unexpected and informal entry into the HR profession, emphasizing serendipity in career beginnings.
“return to office. And I started laughing because I thought, wait, no, this is not quick and this is probably not a win for most folks.”
This illustrates a realistic and empathetic perspective on return-to-office mandates, contrasting with an overly optimistic executive view.
“we expect our leaders, so myself included, to be able to really set a strategy, and to be able to do the work of somebody on their team at the same time.”
This quote encapsulates Brex's 'operate at all levels' philosophy, promoting leaders who are both strategic and hands-on.
“If there is a CEO that says no to that, to me, that's almost a flag in itself. To me, there's actually mutual benefit in us exploring some really difficult conversations before we even start working together.”
This emphasizes the critical importance of a CPO's values alignment with their CEO and the benefit of pre-emptive difficult conversations.
“I always say, you've got this. This is a really tough role, function, time to be in people. And so, as much as you can continue to build your community and the people around you, it's the best advice I've gotten.”
This offers empathetic encouragement and highlights the crucial role of community and support networks for HR professionals.
The problems this episode addresses
- •Organizations struggle to implement RTO policies effectively, balancing demands for connection with employee desire for flexibility without damaging culture.
- •Companies face challenges in developing leaders who can seamlessly switch between high-level strategy and hands-on execution, often resulting in disconnects between leadership and day-to-day operations.
- •Identifying and retaining high-potential and critical talent is a consistent pain point, as generic retention strategies fail to address the specific needs of top performers.
- •New CPOs and senior HR leaders often lack a clear, proactive playbook for their initial 90 days, risking delayed impact or misaligned priorities without rapid internal and external understanding.
- •Misalignment of values and strategic vision between a Chief People Officer and the CEO can lead to significant organizational friction and an unproductive tenure for the CPO.
In this episode
Heather is the head of people at Brex. com
Built by People: Heather's Career
Brex balances return-to-office mandates with flexibility while maintaining culture
Return-to-Office Mandate
Brex develops managers who can seamlessly switch between strategy and hands-on execution
Brex 3.0: How to Build Connective Leaders
Brex is refining its system to spot high potential employees early and keep them engaged
Brex Talent Selection and Retention System
For a new chief people officer stepping into the role, what's your playbook
Onboarding a Chief People Officer: The 3-month playbook
Heather, I want to talk about reverse interviewing for fit. When sizing up an organization as a potential employer
Reverse Interviewing for Fit
Heather shares some parting advice with the Built by People community
A Taste of Built by People
Topics covered
Organizations and entities mentioned
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