From Vision to Execution: Leadership, Strategy & AI with Jason Andrews (VP, Cisco)
What does it really take to turn strategy into execution inside one of the world's largest tech companies? In this episode of The Varun Kapur Show, Varun sits down with Jason Andrews, Vice President of Strategy and Planning at Cisco, who leads engineering operations for Cisco Networking - a $40B+ business with over 22,000 people, a million square feet of lab space, and 2.4 million devices across 300 locations. Jason opens up about the moment that changed his career trajectory, the setback that taught him never to chase titles and paychecks, and why "working hard is not a strategy." He breaks down how leaders at scale decide what deserves a yes and what gets a firm no, why feature velocity is the most overrated metric in engineering, and what being truly "AI-first" means beyond faster coding. From automating away the work you hate, to putting robots in Cisco's labs, to a career-defining 30-minute conversation with GameStop's late CEO Paul Raines, this conversation is packed with grounded, practical lessons for anyone navigating leadership, technology, and change. In this Episode: The career turning point that made Jason intentional about his time and energy, and why he recommends getting an MBA 8-10 years into your career "Everything is a lesson": what being a janitor, a waiter, and a financial services employee taught him about leadership The setback of chasing a title and a paycheck, and how his network got him back on track Why "working hard is not a strategy," and what Blockbuster vs. Netflix teaches us about scenario planning. How to say no: the 3-5x return rule for deciding which ideas deserve investment. The real blockers slowing engineering organizations: legacy systems, tech debt, and dependencies. Why feature velocity doesn't tell the full story, and the questions leaders should ask instead. What "AI-first" actually means: fixing the whole ecosystem, not just code velocity - testing, security, governance, and a human in the loop. The three skills that will matter most in the next five years: curiosity, AI literacy, and data fluency. "Find the work you hate, and start there" - Jason's advice for getting started with AI. Leading with genuine care: "The people are the product". The "dumb idea" about robots that turned into a real program with the University of Texas. Migration vs. transformation: the Atlassian stack overhaul nobody thought was possible. Life outside work: sports photography, building furniture, and watching his daughter play soccer and rugby. Lightning round: the one book every leader should read, the most overhyped technology, and a dream dinner guest (Robin Williams). "It's the person that makes the person" - Jason's humble origin story. The legacy he hopes to leave: principles, honesty, and doing it the right way. Quote of the episode: "Don't worry about AI taking your job. Worry about the person that understands AI taking your job." - Jason Andrews 🎙️ The Varun Kapur Show - new episodes on leadership, technology, and AI 👤 Guest: Jason Andrews, VP of Strategy and Planning, Cisco 🎧 If you enjoyed this episode, please follow, rate, and share the show! #Leadership #AI #Strategy #Cisco #Engineering #TechPodcast #TheVarunKapurShow
