Anthropic Member of Technical Staff on Leading Forward-Deployed Engineers, Turning Down 2x Pay, and Why Leaders Are Becoming ICs Again | Amandeep Khurana | E310

What do you do after you've founded a company, sold it to Databricks, and could coast? Amandeep Khurana went back to being hands-on. In this episode of The Product Podcast, Carlos Gonzalez de Villaumbrosia (CEO at Product School) talks with Amandeep Khurana, now on Anthropic's go-to-market team, about a career built on deliberately choosing the harder path. Amandeep traces the whole arc: training as an engineer, moving to the Valley to go customer-facing at Cloudera, catching the company-building bug "by osmosis," and founding Okera in 2016, which eventually exited to Databricks. He talks about what he learned in the ups and downs of running a startup, why he later joined AWS as a founding PM (on Kiro) to run four zero-to-one initiatives instead of taking a comfortable management track, and how he thinks about the two fundamental jobs in any company: building a product and selling a product. He and Carlos dig into the tension between being a hands-on builder and being a manager, how to decide which domains are worth jumping into when you know nothing, and why he joined Anthropic to work on bringing AI safely to enterprises. It's a candid conversation about career design, first-principles decision-making, and staying close to the work. What you'll learn: - Why Amandeep repeatedly chooses the "harder path," and how first-principles thinking drives his career decisions - What founding and exiting Okera (to Databricks) actually taught him about company building - Why he went back to hands-on building instead of a pure management track - How to think about the two core jobs in any company: building the product and selling it - How to decide whether to jump into a domain you know nothing about - What running four zero-to-one initiatives inside a big company teaches you - Why he moved into GTM and enterprise AI adoption at Anthropic - How to stay hands-on as your career pulls you toward management Connect with Amandeep Khurana: Anthropic (GTM / Enterprise); previously co-founder and CEO of Okera, founding PM for Kiro at AWS LinkedIn: https://www.linkedin.com/in/amansk/ Host: Carlos Gonzalez de Villaumbrosia, CEO at Product School LinkedIn: https://www.linkedin.com/in/villaumbrosia/ About the Product Podcast: Product School's podcast brings you candid conversations with the founders and product leaders shaping tech. Social Links: Find out more about Product School here Follow our Podcast on TikTok here Follow Product School on LinkedIn here