Becoming Better with StartupExperts

Recorded live at Transform 2026, Benji shares the journey of building Ashby—from early research and deep customer conversations to creating a product designed for increasingly tech-savvy People teams. He dives into key lessons from scaling a fast-growing company, including the importance of hiring with discipline, documenting clear operating principles, and maintaining strong alignment between fou...

Recorded live at Transform 2026, Dutta shares key takeaways from a panel discussion on one of the most important questions facing organizations today: as AI adoption accelerates, who ultimately owns the risk? He explores the need for strong governance frameworks, the importance of maintaining both efficiency and quality, and why keeping a human in the loop is critical when deploying AI in the work...

Recorded live at Transform 2026, guest host Michelle Arietta sits down with Jeet Mukerji, CEO and co-founder of Kinfolk, to explore how AI is reshaping the way People teams operate. With a background in AI and HR tech, Jeet shares the story behind building Kinfolk—a platform designed to remove friction from work by automating repetitive but critical HR processes. In this conversation, they cover:...

Recorded live at Transform 2026, Payal Maheshwari sits down with Jared Kleinert, CEO of Offsite and a valued StartupExperts partner, for a conversation on why intentional in-person experiences still matter—especially in a remote and hybrid world. Jared shares his background in the People space, his early experience at 15Five, and the journey that led him to build Offsite, a company helping teams p...

Recorded live at Transform 2026, Payal Maheshwari sits down with JC Ramos from Network Right to unpack one of the most overlooked challenges in startups today: building the right IT foundation early. JC shares his journey from cybersecurity sales to partnerships at Network Right, and how his experience—and even a layoff—led him to a company focused on helping startups scale smarter through fractio...

Recorded live at Transform 2026, Camino shares insights from working closely with People leaders and highlights what sets high-performing teams apart—intentionality, iteration, and a strong focus on human connection. He explores the balance between technology and the human experience, emphasizing that while AI can support efficiency, meaningful onboarding and workplace culture are still deeply hum...

Recorded live at Transform 2026, Boost shares his journey into the StartupExperts community and reflects on the power of connection—especially during moments of transition and change. From finding support after a layoff to building meaningful relationships, his story highlights the importance of community in career growth. Boost also dives into some of the biggest questions shaping the future of P...

Recorded live at Transform 2026, Farrah shares her experience as a first-time attendee and reflects on the power of community—from reconnecting with a life-changing mentor to instantly finding belonging within the StartupExperts network. Farrah dives into key insights from the event, including how trust is built through shared experiences, the role of fun in strengthening teams, and the importance...

In this episode of Conversations with SuE Live at Transform 2026, Payal Maheshwari sits down with Misty Dodd, a StartupExperts member attending Transform for the first time. Misty shares her journey of transitioning from Canada to the U.S. and how StartupExperts has played a key role in helping her build community, navigate new professional landscapes, and grow her network. She highlights the valu...

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...

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...

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 an...

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, he...

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 fa...

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 syst...

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...

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 s...

In this episode of Becoming Better with StartupExperts: 25 Leaders to Follow in 2025 series, Jesse Freese sits down with Eliza Bell, an experienced People Leader and consultant who currently serves as a fractional Head of People for multiple clients. Eliza shares her unique journey into HR — from working in the startup world at a company called Kitchen Surfing to leading People teams in robotics a...

In this episode of Becoming Better with StartupExperts – 25 Leaders to Follow in 2025, Jesse Freese sits down with Tanaz Mody Operating Partner at Lerer Hippeau, to explore what it means to build people-first organizations from the ground up. Tanaz shares lessons from her journey across early-stage startups and venture, offering candid insights on how culture and leadership must evolve as companie...

In this episode of Becoming Better with StartupExperts — 25 Leaders to Follow in 2025, Jesse Freese sits down with Ashley Hall, Head of People and Culture at Cocokind, a Bay Area skincare brand redefining beauty with authenticity and sustainability. Ashley shares her nonlinear journey from horticulture and environmental work to startup leadership, and how she’s cultivated a people-first culture th...

In this episode of Becoming Better with StartupExperts, Jesse Freese sits down with Maggie Ruvoldt, Chief Human Resources Officer at LEARN Behavioral and one of StartupExperts’ 25 Leaders to Follow in 2025. With over 30 years of experience in HR, Maggie shares her journey from aspiring social worker to becoming a seasoned people leader who believes that HR sits at the heart of every great business...

In this episode of Becoming Better with StartupExperts, Jesse Freese sits down with Sreyas, Head of People and Talent at Stay AI, and one of this year’s 25 recognized community leaders within StartupExperts. Sreyas shares her journey from starting in recruiting to leading people operations in fast-growing tech companies, including her current work in the AI space. She discusses the evolution of he...

In this “25 Leaders to Follow in 2025” edition of Becoming Better with StartupExperts, Jesse Freese spotlights Patrick Sutton—his pivot from film to people leadership, two decades across Fortune 500, public sector, startups, and back again, and the people-first philosophy that anchors his work. Patrick opens up about the habits that shaped him (including his “1% better every day” lens), hard-won l...

In this episode of Becoming Better with StartupExperts, Jesse Freese sits down with Bob Starr, VP of Human Resources at Zap Surgical Systems and one of our 25 Leaders to Follow in 2025. Bob reflects on his 20+ year career in HR — from his early days at Atari to leading people operations at innovative medical device companies. He shares lessons learned along the way, including: Why vulnerability ca...

Jesse sits down with Emily—recently named one of our “25 Leaders to Follow in ’25” and our VP of Learning & Content—to talk about leading through curiosity, building a culture of learning, and why giving back compounds impact. In this conversation, Jesse thanks Emily for her outsized contributions to our community and team, spotlighting why she was selected as one of our 25 Leaders to Follow i...