Matt Wilson, Co-Founder & CEO at Jack and Jill, on AI Career Agents, Talent Density, and Building the Next Network-Effect Marketplace

Matt Wilson, Co-Founder & CEO at Jack and Jill, on AI Career Agents, Talent Density, and Building the Next Network-Effect Marketplace

From Riding Unicorns: Venture Capital | Entrepreneurship | Technology by Riding Unicorns Productions

March 11, 2026 · 36 min · Season 9 · Episode 26

About this episode

Matt Wilson discusses AI Career Agents and the future of job hunting with a focus on his company Jack and Jill.

This week on Riding Unicorns, Matt Wilson returns to the podcast. Matt previously joined us in September 2022 to talk about Omnipresent, which has since been acquired by Deel. He is now back building Jack and Jill, one of the most talked-about venture-backed companies in Europe right now. Jack and Jill is bringing conversational AI to job hunting and hiring, with two agents built for two audiences: Jack, an AI agent for individuals that learns who you are, what you want, and monitors the job ...

People in this episode

Guest: Matt Wilson

Topics covered

  • AI Career Agents
  • Talent Density
  • Job Hunting
  • Hiring
  • Venture Capital
  • Marketplace

Keywords

  • AI
  • job hunting
  • hiring
  • venture-backed
  • marketplace
  • conversational AI
  • talent density

Mentioned in this episode

Organizations: Jack and Jill, Omnipresent, Deel

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