#40 How FirstWork Closes AI Pilots in 7 Days and Lessons from Scaling Engineering at Rippling and Deel | Shubham Choudhary

Episode notes

I'm joined by Shubham Choudhary, co-founder and CTO of FirstWork (YC S24), who is using his extensive experience at Rippling and Deel to reshape the frontline HR tech space. In this episode, we unpack how he’s using agentic AI, a custom rules engine, and battle-tested global compliance experience to outpace incumbents with lean teams and real-time automation — all while closing enterprise AI pilots at scale. Timecodes: 0:00 - Introduction 1:06 - What is FirstWork and Why Build It Now? 11:01 - Lessons from Scaling Global Products at Rippling and Deel 19:20 - Why YC Asked FirstWork to Hire Fast 20:02 - Rippling's ‘Under-One-Roof’ Model Applied to Frontline HR 23:12 - Hiring Anxiety and the Case for Delegation 26:05 - Using AI for Validation Over Generation in HR Use Cases 29:38 - Enterprise Pilots: AI + SOPs → Fast Iteration 36:46 - Hiring Lessons from Deel, Rippling, and Startup #1 49:55 - FirstWork’s Sprint Cadence and No-Ceremony Culture 51:10 - Rapid Fire: Advice, Book, Product, and ChatGPT as Co-Pilot 56:00 - How to Reach Shubham and Closing Remarks Important links: FirstWork: Inbound-led-outbound motion made easy for LinkedIn without breaking their terms of service.