The Staffing Show AI and Staffing with Jonathan Kestenbaum
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Aug 1, 2025 Jonathan Kestenbaum, Managing Director at AMS and a seasoned entrepreneur in the work tech sector, shares his insights on the intersection of AI and staffing. He discusses the transformative potential of AI, tackling both the challenges it presents and the new opportunities it can create. The conversation covers the evolution of recruitment through technology, the importance of compliance, and the shift towards contract staffing models. Kestenbaum also touches on personal influences and habits that fuel success, painting an optimistic view of the future of recruitment.
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From Tutoring Auctions To Talent Tech
- Jonathan started as a licensed attorney and built a reverse-auction platform for tutors that became work tech.
- He sold that company, co-founded Talent Tech Labs, and spent his career evaluating and building work tech.
Fit Buyers' Budget Categories
- Sell into existing budget categories rather than inventing new labels to capture buyer spend.
- Align your product messaging to buyer business problems, not vendor feature lists.
AI Expands Beyond Predictive Matching
- Generative AI now performs conversational and creative tasks that previously only humans could do.
- Staffing tech must redesign human roles constantly as AI eats more tasks over time.