AI and the Future of Work: Artificial Intelligence in the Workplace, Business, Ethics, HR, and IT for AI Enthusiasts, Leaders and Academics 368: Match Humans, Not Keywords: Inside Jobright’s AI Talent Matching with Serial Entrepreneur Eric Cheng
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Dec 22, 2025 In this discussion with Eric Cheng, co-founder and CEO of Jobright, listeners learn about the transformative power of AI in job matching. Eric reveals how interviewing 150 young professionals led him to create a personalized career support platform. He critiques traditional keyword-based job searches and explains how Jobright acts as a career coach, emphasizing the importance of trust in AI hiring. The conversation also covers emerging AI-native roles and the need for continuous learning in an evolving workplace.
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Finding Jobright From 150 Conversations
- Eric Cheng interviewed about 150 young professionals during a gap year and helped 10 of them get jobs through personalized guidance.
- He used those conversations to realize many candidates limit themselves to familiar roles and need broader career coaching.
Hiring Is A Complex Matching Problem
- Hiring is fundamentally a complex, non-standard matching problem with tens of thousands of factors beyond keywords.
- Eric Cheng argues search engines fail because humans (referrals, headhunters) have far richer context and reasoning than keyword systems.
Make AI Your Personal Career Coach
- Use AI to act like a domain expert, not to spam applications; build a system that identifies strengths and recommends qualified jobs.
- Only apply where fit is strong, polish truthful resumes, and pursue targeted referrals.