Becoming Better with StartupExperts

In this final Becoming Better at StartupExperts episode of the year, Jesse sits down with Holly Hatlo, Lead HR Business Partner at Hatch and one of our 25 Leaders to Follow in 2025.
Holly shares her career journey through the startup ecosystem—from early-stage growth at DoorDash to leading people strategy at Hatch—and reflects on the moments that shaped her most as an HR and People Ops leader. She speaks candidly about the power of community, the importance of belonging, and how StartupExperts has influenced not only her professional growth, but how she shows up as a human.
The conversation dives into practical leadership lessons, including embracing “wet paint” work, learning faster through iteration, empowering managers, and why asking better questions matters more than having all the answers. Holly also opens up about her love of reading, book clubs, and the personal connections that make this work meaningful.
A thoughtful, energizing conversation on leadership, humility, curiosity, and what it truly means to grow—together.

In this episode of Becoming Better with StartupExperts, Jesse Freese sits down with Elisabeth Woodfield, one of our Leaders to Follow in 2025, for a thoughtful conversation on modern talent leadership, simplicity, and the evolving role of AI in recruiting.
Elisabeth shares her journey from Goldman Sachs to leading talent teams in high-growth startups, including her upcoming role as Head of Talent at Centrelink. Together, they explore how talent acquisition is shifting from a transactional function to a deeply human, relationship-driven practice.
The conversation dives into the power of simplicity as a leadership principle, how AI can free teams to focus more on meaningful human connection, and why aligning recruiting efforts with business strategy creates better outcomes for candidates, teams, and companies alike.
This episode is part of our Becoming Better short-form conversations, where we spotlight exceptional leaders in the StartupExperts community and share their perspectives, lessons learned, and practical wisdom.

In this episode of Becoming Better with StartupExperts, Jesse sits down with Dave Carhart, one of our 25 Leaders to Follow in 2025 and a long-time contributor to the StartupExperts community. Dave shares his career journey from technical recruiting in Milwaukee to leading HR teams through hyper-growth, IPO, and acquisition — and eventually transitioning into his current role as a fractional CPO and compensation/AI consultant.
The conversation explores Dave’s reflections from his time on the StartupExperts Executive Leadership Team, how the community became a lifeline for him during the pandemic, and why emotional resilience and self-management have become central to his leadership philosophy. Dave also dives into his unexpected passion for gardening, the lessons it taught him about patience and limitations, and how those same lessons show up in HR and fractional consulting.
Jesse and Dave discuss the evolving role of AI in HR, the mindset shift required to think like a product manager, and the power of experimentation as a career and life strategy. Dave closes by sharing a powerful piece of advice for the community: stay curious, try things, and keep experimenting — especially as AI reshapes the future of work.
A thoughtful, candid conversation with a leader who has been instrumental in shaping the StartupExperts community.

In this episode of Becoming Better with StartupExperts, Jesse sits down with Chelsea Gregory, Head of Global HR at Suki and one of StartupExperts’ “25 Leaders to Follow in 2025.” Chelsea shares her remarkable journey from teaching in Spain to joining Suki as an office manager in 2018 and growing into a senior HR leadership role.
The conversation explores her parallel growth with StartupExperts, her passion for cultivating meaningful employee experiences, and her commitment to supporting teams during rapid scale. Chelsea opens up about personal “cringe moments,” the value of vulnerability, what she’s learned through leading our AI Roundtables, and how embracing humanness is critical to thriving in an increasingly tech-driven world.
Chelsea also offers insight into what’s ahead for Suki in 2026, how the organization is preparing for significant growth, and the importance of preserving culture while scaling globally.
A thoughtful, grounded, and inspiring conversation—perfect for HR, Finance, and Ops leaders looking to lead with authenticity and curiosity in a changing world.

In this Becoming Better short-form conversation, Jesse sits down with Shayne Kuhaneck, Sr. Vice President of Finance of Fanatics Betting and Gaming and one of StartupExperts’ 25 Leaders to Follow in 2025.
Shayne shares his remarkable career journey — from serving on a nuclear submarine in the U.S. Navy, to technical leadership roles at the Financial Accounting Standards Board, to navigating the fast-moving world of tech at Meta, and now helping build a true startup environment inside Fanatics Betting & Gaming.
Together, they explore Shayne’s passion for travel, his commitment to continuous learning, and how adopting technology can unlock more strategic thinking and team development. Shayne also reflects on meaningful lessons from his career, including the power of over-communication, relationship-building, and bringing others along during times of change.
This episode offers insightful perspectives on leadership, adaptability, and how finance professionals can evolve in a rapidly changing world.

In this episode of Becoming Better with StartupExperts, Jesse sits down with Sarika Lamont, Chief People Officer at ARD and one of our 25 Leaders to Follow in 2025.
Sarika shares her unique, nontraditional path into HR—beginning in sales and marketing at Philip Morris, moving into management consulting, and eventually stepping into senior HR leadership through a deep understanding of business systems, people strategy, and organizational scale.
Together, Jesse and Sarika unpack lessons from building fast-growing organizations, bridging the gap between business and people teams, and gaining credibility as a talent leader without a traditional HR background. She reflects on leading through transformational moments, including today’s rapid AI shift, and how pausing before reacting has reshaped her leadership style.
Sarika also offers candid advice on navigating careers with a “lattice mindset,” the importance of leaning into your strengths, and how choosing fulfillment and impact—rather than titles—ultimately leads to better growth and better leadership.
A thoughtful, energizing conversation with one of the most grounded and strategic CPOs in our community.

In this episode of Becoming Better with StartupExperts, Jesse sits down with Heather Dunn, Chief People Officer at Brex and one of our 25 Leaders to Follow in 2025.
Heather shares her journey from starting in HR at just sixteen to leading people strategy at some of the most innovative companies in tech. She opens up about the lessons learned along the way — from navigating cultural misalignment to redefining what balance and fulfillment look like in leadership.
Together, Jesse and Heather explore how slowing down, listening to your instincts, and staying true to your values can transform both how you lead and how you live. Heather also gives us a glimpse into Brex’s bold new talent philosophy, “Be the founder of your career,” and how it’s reshaping the future of work.
 
Tune in for a thoughtful, honest conversation on growth, self-awareness, and what it really means to become better.

In this episode of Becoming Better with StartupExperts, Jesse Freese sits down with Adam Hill, seasoned startup leader and one of StartupExperts’ 25 Leaders to Follow in 2025.
Adam shares his journey through the startup ecosystem — from co-founding an accelerator in North Carolina to leading People Operations and recruiting for venture-backed tech companies in New York. Now at Sidecar, a FinTech supporting early-stage investors, Adam reflects on what he’s learned across five startups and one recent acquisition.
Together, Jesse and Adam explore the realities of startup leadership: building processes that scale, learning from hindsight moments, and balancing ambition with well-being. Adam also shares his insights on the evolving role of AI in hiring and the importance of staying intentional about your career — from setting clear expectations to knowing when to walk away.
Tune in for an honest, down-to-earth conversation about growth, reflection, and leading with intention in the fast-paced world of startups.