Episode 504: Should I quit my AI job before my first day and professional button-clicker

Episode 504: Should I quit my AI job before my first day and professional button-clicker

From Soft Skills Engineering by Jamison Dance and Dave Smith

March 16, 2026 · 32 min

About this episode

Dave and Jamison discuss the dilemma of choosing between a job at a fast-growing AI company and a more recognizable brand name tech company.

In this episode, Dave and Jamison answer these questions: Hi Jamison and Dave. Eight years into my software engineering career, all of it at Series B and C startups, I’ve been craving two things: a recognizable brand name on my resume and the chance to work on real scale problems. After a long search, I finally got both. The catch? I got them in the wrong order. I accepted an offer at one of the hottest and fastest-growing AI companies in the application layer space. Exciting work, smart people, real momentum, but not quite a household name yet, and not quite facing the kind of scaling challenges that come with a billion users yet either. Two weeks later, I finally heard that I cleared the interviews from a big brand name tech company. I’ll be honest: it wasn’t my first choice brand name. I bombed interviews at a few others and this was basically my consolation prize. Here’s the thing about this mega tech company right now: the culture has … shifted. It feels less like a tech company and more like a social experiment with a $1.5 trillion market cap. So now I’m torn and the clock is ticking. My start date at the AI company is in a few weeks and I’m currently in team matching at…

People in this episode

Hosts: Jamison Dance, Dave Smith

Topics covered

  • career decisions
  • job offers
  • company culture
  • software engineering
  • AI industry
  • scaling challenges

Keywords

  • job offer
  • AI job
  • career change
  • company culture
  • software engineering
  • scaling problems

Mentioned in this episode

Organizations: AI company, mega tech company, Series B and C startups

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