Becoming Better with StartupExperts

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Apr 2026

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About the show

This podcast is about amazing people, their perspectives on our ever-changing world, and more specifically how we adapt to these changes as leaders. My name is Jesse Freese and this podcast is about Becoming Better with StartupExperts.

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36 recent

April 23, 202620 min

Conversations with SuE: Benji Encz on Scaling Startups, Hiring with Discipline & Building Culture

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 founders and People teams.Benji also explores how AI is changing the recruiting landscape, enabling teams to operate more efficiently while raising the bar for technical fluency across HR and talent functions.From founder-led culture to the future of recruiting technology, Benji offers a thoughtful and practical perspective on what it takes to build and scale high-performing teams.Tune in for an insightful conversation on hiring, culture, and the evolving role of People teams in a rapidly changing world!

April 23, 202613 min

Conversations with SuE: Dutta Satadip on AI Risk, Compliance & the Human in the Loop

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 workplace. Dutta also highlights how company culture—especially around ownership and accountability—plays a key role in managing risk effectively.Beyond AI, Dutta reflects on broader themes from Transform, including the growing importance of change management and the challenges organizations face in helping teams adapt to rapid technological shifts.Whether you're navigating AI adoption, managing compliance, or supporting global teams, Dutta’s insights offer a thoughtful perspective on balancing innovation with responsibility.Tune in for an insightful conversation on AI, risk, and building human-centered systems in a rapidly evolving world!

April 23, 202613 min

Conversations with SuE: Jeet Mukerji on AI, HR & Agentic Workflows

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:What “agentic AI” actually means for People teamsHow HR can move beyond repetitive tasks and focus on higher-impact workWhy knowledge bases matter more than ever in AI adoptionHow leading organizations are approaching AI readiness and change managementThe shift from experimenting with AI to driving real ROIJeet also shares practical advice for People leaders navigating the next phase of AI adoption—from rethinking workflows to building internal capability before investing in new tools.Whether you're early in your AI journey or looking to scale your efforts, this conversation offers a grounded and practical perspective on what it takes to implement AI effectively in the workplace.Tune in for insights on AI, HR, and building more efficient, human-centered systems!

April 23, 202614 min

Conversations with SuE: Jared Kleinert on Remote Work & Building Connection

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 plan more effective and engaging offsites at scale.In this conversation, they explore:Why offsites are more than just a perk—they’re a strategic investmentHow remote and hybrid companies can think about connection, alignment, and cultureWhat leaders often miss when evaluating the cost of gathering in personWhy many teams still want a human partner, even in an AI-driven worldTrends Jared is seeing across startup clients as companies rethink work, engagement, and ROIJared also shares practical insight into how companies can plan more intentionally, reduce unnecessary spend, and create experiences that actually support team performance.Whether you're leading a People team, planning an all-hands, or rethinking how your company gathers, this conversation offers a thoughtful look at the value of bringing people together.Tune in for a practical conversation on offsites, culture, and building stronger teams through intentional connection.

April 23, 202614 min

Conversations with SuE: JC Ramos on IT, AI & Scaling Smart in Startups

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 fractional IT and security support.In this conversation, they explore:Why IT often becomes a bottleneck as startups growThe hidden cost of “just making it work” in early-stage teamsHow to internally advocate for external support and resourcesThe role of AI in enabling (not replacing) teamsWhy human support still matters in high-stakes, real-world scenariosThe importance of community for operators working as teams of oneJC also shares insights on what high-performing startups do differently—from investing early in infrastructure to staying intentional about how teams spend their time.Whether you're in HR, operations, or leadership, this conversation offers practical advice on scaling efficiently without sacrificing focus.Tune in to learn how to build smarter systems—and stronger teams—from the ground up!

April 23, 202614 min

Conversations with SuE: Kevin Berry on Rethinking Onboarding & Human-Centered HR

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 human challenges. Camino also reflects on evolving trends in HR, from AI adoption to the growing need for connection, belonging, and sustainable ways of working.Whether you're building onboarding programs, scaling People teams, or navigating the intersection of AI and culture, Camino’s perspective offers practical and thoughtful guidance on creating better experiences for employees.Tune in for an insightful conversation on how to build more intentional, human-centered workplaces!

April 23, 202613 min

Conversations with SuE: Boost on AI, Performance & the Future of People Teams

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 People teams today. From reimagining performance management to exploring how AI may transform the role of HR generalists, he offers a thoughtful and grounded perspective on balancing innovation with responsibility.Whether you're leading through hypergrowth, adapting to new technologies, or thinking about the future of work, Boost’s insights will challenge you to think more deeply about how we build, support, and evolve our teams!

April 23, 20266 min

Conversations with SuE: Farrah Mitra on Building Community & Finding Your Voice

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 of connection in a world facing increasing loneliness. She also opens up about her personal journey of finding her voice and having the courage to share it with others.Whether you're leading teams, navigating personal growth, or seeking deeper community, Farrah’s perspective is a powerful reminder of the impact of connection, vulnerability, and showing up fully.Tune in for an inspiring and heartfelt conversation with one of the standout leaders to watch in 2026!

April 23, 20263 min

Conversations with SuE: Building Community & Perspective with Misty Dodd at Transform 2026

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 value of the Slack community as a space for both learning and giving back.The conversation also touches on an insightful takeaway from the conference—AI bias in talent and HR systems—emphasizing the importance of thoughtful implementation and governance.Overall, the interview captures the spirit of StartupExperts: connection, support, and continuous learning.

December 23, 2025Episode 2619 min

Leading with Simplicity: Elisabeth Woodfield’s thoughts on Human-Centered Talent Leadership in the Age of AI

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.