Farrah shares her unique career journey from strategy consulting to building people and culture functions in hypergrowth tech companies, and now coaching leaders on how to communicate with clarity and empathy.

The conversation explores her Communicating Challenges and Change Framework, designed to help leaders deliver difficult messages in a way that is both kind and clear—especially in today’s fast-changing, high-pressure environments.

You’ll learn:

• How to balance empathy with directness in leadership communication
• Why mindset matters just as much as skillset
• A practical approach to navigating tough conversations with confidence
• Real-world examples of delivering feedback and driving change
  

If you're a leader, operator, or manager navigating constant change, this episode offers actionable insights you can apply immediately.

• Why relationship — not programming — is the true point of community
  
• How the Go-Giver philosophy shapes SuE’s culture
  
• What it takes to move from passive membership to active participation
  
• How StartupExperts is building systems to scale without losing connection
  
• The importance of designing touchpoints for both in-person and virtual members
  

Meica also shares how her team is reimagining onboarding through a “gifts conversation” approach — asking members what they want to contribute, not just what they want to receive.

If you care about leadership, community-building, and creating spaces where operators genuinely support one another, this conversation is for you.

Subscribe for more conversations with leaders from the StartupExperts community!

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. She opens up about the power of feedback, the importance of courage in difficult moments, and the subtle ways our language shapes how we lead.

Together, Jesse and Maggie explore what it means to stay truly open to learning — even when we think we already are — and how to navigate the evolving intersection between human leadership and AI. Maggie also reflects on the art of building genuine relationships, offering timeless advice: “Treat your network like a bank account — make deposits when you don’t need it.”

It’s a thoughtful, grounded conversation about growth, humility, and the strength that comes from leading with empathy and intention.

Adriana shares her perspective on what it means to build cultures that align performance with purpose, how impact initiatives can drive business growth, and why intention matters more than perfection. Whether you're leading People, Ops, or Finance, her insights will challenge and inspire you to lead with greater clarity, conviction, and care.

Tune in for a thoughtful, practical conversation on building better companies—inside and out.

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.

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.

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.

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 can be a powerful leadership tool.

• The importance of making the right hiring decisions.

• How stepping outside of HR into other functions can make you a stronger leader.

• His excitement about the potential of AI in the workplace and the groundbreaking technology Zap is developing to transform cancer treatment and beyond.

This conversation is part of our special series highlighting the 25 Leaders to Follow in 2025, where we celebrate the stories, wisdom, and perspectives of standout community members.

Tune in to hear Bob’s journey, his insights on leadership, and his advice for the next generation of HR professionals.

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 her career, lessons learned from scaling teams, and what it means to bring a “builder mindset” to leadership — empowering others to create, experiment, and grow using the tools and technology available today.

The conversation touches on themes that resonate across the StartupExperts community:

• The importance of finding your professional community early — and learning through others’ experiences.

• How AI is transforming people and talent work, and how leaders can embrace innovation without losing the human touch.

• The value of self-awareness and confidence — knowing your unique strengths and using them intentionally throughout your career.

Sreyas’s thoughtful perspective is a great reminder that growth comes not just from expertise, but from connection, curiosity, and a willingness to build alongside others.

Ashley shares her nonlinear journey from horticulture and environmental work to startup leadership, and how she’s cultivated a people-first culture that mirrors Cocokind’s mission to be a community-first brand. She reflects on her biggest leadership lessons—like the importance of “not trusting the textbook” and knowing when to evolve programs that have outlived their usefulness.

The conversation also explores how slowing growth can actually unlock creativity, why in-person connection is a cultural investment, and how great leaders empower rather than protect their teams.

It’s an inspiring chat about growth, adaptability, and the human side of leadership.

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.

Fredo shares his journey and perspective on what it means to lead with resilience, innovation, and authenticity in today’s rapidly evolving landscape. From navigating complex challenges to championing inclusive growth, his leadership offers a blueprint for balancing vision with execution.

Whether you’re driving strategy in People, Operations, or Finance, Fredo’s insights will push you to rethink how leadership can inspire not only organizational success but also meaningful change in the communities we serve.

Tune in for an inspiring and practical conversation with one of the standout leaders to watch in 2025.

In this discussion we learn why she chose to serve in the US Military, how she transitioned from the US Navy to her current HR role, and why social impact volunteering is so important to Veterans. 

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.

Together, Jesse and Eliza explore the evolving role of HR and leadership, discussing how traditional systems like performance reviews and engagement surveys are being reimagined for a more human-centered future. Eliza reflects on lessons learned from leading StartupExperts Leadership Circles, offering thoughtful insights on community, experimentation, and rethinking long-standing structures in People Operations.

From embracing change to speaking up even when it’s uncomfortable, Eliza’s perspective reminds us that great leadership isn’t about having all the answers — it’s about staying curious, connected, and courageous enough to try something new.

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 in 2025. Emily reflects on what it means to lead learning-first: creating simple systems that make growth habitual, turning feedback into fuel, and designing content that meets people where they are.

Together they unpack practical ways leaders can nurture engagement—how to scaffold learning so it sticks, invite participation without pressure, and translate insights into everyday behaviors. Emily also shares how service and mentorship shape her approach, and why consistent, small improvements beat big, sporadic initiatives.

Jesse reflects on a recent conversation with his daughter that reminded him of two core values he carries with him in work and in life: curiosity and kindness. Together, Jesse and Alan explore how those values influence the way leaders show up, build relationships, and continue to grow.

Listeners will also catch a lighthearted “easter egg” moment (hint: Watergate 👀) that reminds us leadership is about being authentic, not perfect.

Join us for this thoughtful, human conversation — and celebrate Alan as 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.

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.

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.

Tanaz shares lessons from her journey across early-stage startups and venture, offering candid insights on how culture and leadership must evolve as companies grow. She reflects on the importance of self-awareness, clear communication, and setting expectations early — not as corporate formality, but as the foundation of trust and alignment within every team.

From navigating tough leadership decisions to experimenting with AI tools that empower founders, this conversation is a reminder that great organizations are built not on frameworks alone, but on empathy, curiosity, and the courage to learn from every chapter.

🎧 Listen now and discover how Tanaz continues to lead with heart, awareness, and intention.