Every general counsel remembers the job they didn't want. For Dina Segal, that job became the foundation for every one that followed, and the reason she now tells rising leaders to stop waiting until they feel ready. Jessica sits down with Dina Segal, Chief Legal Officer of Gusto to talk about her path from early litigation and tax work to becoming CLO, and what she has learned about building fearlessness, hiring for AI fluency, and running legal teams through a period of rapid change.
Meet the expert
Dina Segal
Chief Legal Officer of Gusto to talk about her path from early litigation and tax work to becoming CLO, and what she has learned about building fearlessness, hiring for AI fluency, and running legal teams through a period of rapid change
Every general counsel remembers the job they didn't want. For Dina Segal, that job became the foundation for every one that followed, and the reason she now tells rising leaders to stop waiting until they feel ready.
Key takeaways
01
How years of litigation, tax, and FCPA work at a law firm built her career foundation
02
Her Miles Morales inspired philosophy on jumping in before you ever feel fully ready
03
How she was promoted to CLO from within Gusto instead of leaving for the new title
04
Her honest advice for attorneys who keep getting passed over for their first GC title
05
Why owning outcomes, not just helping or contributing, is what recruiters want to see
06
How Gusto hires for AI fluency and gives candidates hands on problem solving exercises
07
Running two legal AI hackathons and turning those ideas into real deployed tools
08
Using AI to monitor thousands of regulatory changes across federal and state law
09
Her work supporting women in legal through Sun Law and what she would build next
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