00:00–02:00 | Introduction Heather Holst-Knudsen introduces Jerry Li, CEO of Gradual and founder of the Engineering Leadership Community (ELC). Jerry’s career journey includes engineering leadership roles at Amazon and Groupon, before turning his passion for community into a business platform.
02:00–05:00 | The Pain of Leadership Jerry explains how his early struggles as a manager—learning slowly and making painful mistakes—drove him to seek out shared knowledge. ELC was born from the need for engineering leaders to learn from each other instead of operating in silos.
05:00–08:00 | Why Meetups Weren’t Enough Despite the abundance of meetups in Silicon Valley, Jerry found them too surface-level and serendipitous. True leadership growth required curated, ongoing peer-to-peer conversations supported by technology.
08:00–12:00 | Engineering + Community Building Jerry’s dual background in engineering and leadership gave him a unique advantage to design Gradual. He built tools to create better user experiences for members while solving pain points for organizers.
12:00–16:00 | The Real Value of Community Jerry highlights that the real value of communities lies beneath the surface—trust, curated groups, and intentional connections. He notes engineers often “like networking, but hate networking,” so structure and facilitation are crucial.
16:00–20:00 | Protecting the Mission ELC succeeded because it stuck to its mission—strictly for engineering leaders. By excluding recruiters and marketers, members felt safe and invested, while outsiders respected (and even wanted into) the exclusivity.
20:00–25:00 | Events as Growth Engines Events became ELC’s foundation, fueling trust and word-of-mouth growth. Jerry stresses that designing events with multiple value layers (insight, belonging, tools, connections) ensures members never leave disappointed.
25:00–30:00 | From ELC to Gradual Gradual was born out of necessity—Jerry’s team coded tools for ELC in 2016 without realizing they were building a platform others would need. Years of iteration created a modular system now serving companies like OpenAI, Fiverr, and Siemens.
30:00–36:00 | The OpenAI Case Study OpenAI’s first community on Gradual began with 200 elite researchers. Over time, it expanded into a global ecosystem, supporting champions, customers, and public education (e.g., OpenAI Academy). Jerry notes community success requires small, focused beginnings that grow gradually.
36:00–45:00 | Communities into Ecosystems Jerry describes how communities evolve into ecosystems where members’ needs naturally introduce sponsors, vendors, and experts—if managed with intention. He outlines revenue models from paid events to sponsorships, while emphasizing that monetization follows genuine value creation.
45:00–47:00 | AI & the Future of Community Jerry envisions AI-powered “agents” that act on behalf of community members, surfacing the right connections, events, and insights without requiring constant presence. AI makes personalized community engagement possible at scale.
47:00–50:00 | Rapid Fire & Closing Jerry shares his favorite book (Extreme Ownership), and a personal story about learning to scuba dive in Bali before he could swim—a metaphor for trust in community. Heather closes with invitations to Revenue Room Connect and upcoming events.
