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: https://www.firstwork.com/

Inbound-led-outbound motion made easy for LinkedIn without breaking their terms of service. - Jerry: https://tryjerry.com

Quirky startup merch: Shop71 at https://shop.7tea1.com

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