Episode 18: Building a Strong People Function in an Early-Stage Startup - with Keshar Sheridan

Our guest today is Keshar Sheridan, a seasoned people leader with deep experience in the startup and health tech space. Keshar has spent more than a decade building HR foundations at organizations ranging from early-stage startups to high-growth companies like Hired, Oscar Health, Galileo, Headway, Growth Therapy, and now Tulea Health, where she serves as the first and only people leader at an 11-person team. In this episode, we dive into the practical realities of being a team of one, what it means to join and scale an HR function at the foundational stage, and how to evaluate companies and CEOs when considering your next leadership opportunity. Jess Yuen and Andrew Bartlow explore with Keshar how early people leaders can set themselves and their organizations up for long-term success, and what it takes to create leverage, influence culture, and build strong leadership relationships from day one. We discuss: What HR looks like at a pre-20-person startup, including balancing tactical operations with strategic planning How to prioritize foundational people programs during the earliest stages of company growth The signals CEOs give when they value the people function, and why bringing in HR early matters Frameworks for deciding when and why to hire your first people leader, covering variables like growth rate, cultural aspirations, and industry context How to assess CEO and organizational fit in the interview process, including why and how to speak with board members or investors Key questions to ask about business models, go-to-market plans, and long-term company goals—even when answers are still forming The importance of mentorship, how to cultivate mentoring relationships organically, and why maintenance matters Strategies for developing trust and alignment with founder-CEOs, especially when feedback and structure may be lacking Why documentation matters as a solo HR leader, and how to build leverage for yourself and future team members Practical productivity tools Keshar uses to stay effective and efficient as a team of one This conversation is full of actionable insights for people leaders at early-stage companies, or anyone considering how to assess fit and make an impact as the first HR hire. Keshar shares concrete advice on building relationships, structuring your work, and trusting your own expertise—even when the playbook is still being written. For show notes and bonus resources, visit www.PeopleLeaderAccelerator.com/podcast. About The People Leader Accelerator Podcast Our goal with this podcast is simple: to help people leaders navigate the messy, complex, and deeply rewarding work of leading teams and organizations with more clarity, confidence, and community. Whether you’re the first HR hire at a startup or an experienced executive at a company with scale, you’ll find actionable insights you can use right away. We can’t wait to share these conversations with you. Welcome to the journey! Listen, learn, and connect: 🎧 Subscribe wherever you get your podcasts (Apple, Spotify, YouTube). 💡 Find show notes and bonus resources at peopleleaderaccelerator.com/podcast. 📬 Share this episode with a colleague who’s ready to level up as a people leader. 🤝 Connect with your hosts: Jessica Yuen: linkedin.com/in/jessicayuen | jessyuen.com Andrew Bartlow: linkedin.com/in/bartlow | peopleleaderaccelerator.com