Building Through Technology Shifts: Lessons from OpenTable, Bleacher Report, Outdoorsy, and Roadtrippers

What does it take to build great products through multiple waves of technological change? In this fireside chat, Ross Schwaber will share lessons from a career shaped by major platform shifts: the pre-cloud era at OpenTable, where software had to work in the physical world; the rise of analytics and personalization at Bleacher Report; marketplace scaling at Outdoorsy; and today’s transition to AI-first product development at Roadtrippers and beyond. He’ll share thoughts on what product and engineering leaders can learn from navigating each shift: how to tell signal from hype, where new interfaces actually change user behavior, and how to adopt emerging technology without losing the fundamentals of great product building. Expect practical lessons on analytics, design, product-engineering collaboration, marketplace dynamics, and what it really means to build AI-native products –About Enrich– Enrich is a private community for senior technology leaders across product, engineering, and technology. Through candid conversations, curated peer groups, expert-led events, and meaningful relationships, members gain fresh perspectives, pressure-test important decisions, and learn from leaders who have already navigated many of the challenges they’re facing. Interested in joining Enrich? Apply to join and a member will be in touch!