368: Match Humans, Not Keywords: Inside Jobright’s AI Talent Matching with Serial Entrepreneur Eric Cheng
Update: 2025-12-22
Description
Eric Cheng is co-founder and CEO of Jobright, the AI career copilot serving more than 550,000 users. After building core backend systems at Box and scaling Fangcloud to acquisition, he turned his focus to fixing what’s broken in hiring. His perspective blends engineering depth with a human-centered approach to matching talent and opportunity.
In this conversation we discussed:
- Why Eric created Jobright after interviewing 150 young professionals and discovering a gap in personalized job search support.
- How Jobright reframes hiring as a “matching” problem and uses AI to function more like a career coach than a job board.
- The limitations of keyword-based search tools and how AI enables more nuanced, human-like job matching.
- Why building trust matters in AI-powered hiring platforms and how Jobright balances efficiency with authenticity and accuracy.
- What the “learning loop” means for job seekers and why Eric believes the mindset shift matters more than the résumé.
- How emerging roles like AI operations and forward deployment engineers reflect deeper changes in how organizations adopt and manage AI.
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