“At some point, founders have to stop babysitting the business — or growth stalls.” — Rohit Kumar

In this episode of Evolving Your Workplace, Carol Schultz sits down with Rohit Kumar, Founder and CEO of Chapter Apps, to explore one of the hardest transitions for founders: knowing when hands-on leadership turns into micromanagement — and how that mindset quietly becomes a bottleneck to growth.

Rohit shares the evolution of Chapter Apps, from its early days as a mobile-first learning platform to its current focus on enterprise AI solutions for sales and employee assistance. He explains why the pivot toward AI was driven not by hype, but by real customer demand — especially the need for instant, accurate answers in high-stakes sales conversations.

The conversation digs into what “babysitting” actually looks like at the CEO level: testing products personally, double-checking team output, and stepping in when managers aren’t driving execution forward. Rohit generously opens up about the deeper reason founders struggle to let go — fear of disappointing customers — and how confidence in the team directly affects a leader’s ability to delegate.

Carol and Rohit also discuss scaling across geographies, co-founding a company with a spouse across time zones, and why relocating to San Francisco has accelerated Chapter Apps’ AI innovation through proximity to partners, platforms, and real-time problem solving.

They close by examining growth constraints, talent challenges, inbound vs outbound sales, and whether roles like Chief of Staff and Customer Success are luxuries — or necessities — for founders who want to stop reacting and start leading.

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