In his role as Managing Director at AMS, Jonathan Kestenbaum is continuing to build a rich career as an entrepreneur in the work tech space. A qualified attorney who has built and evaluated a plethora of work tech companies, Kestenbaum considers 2025 the most exciting time to work in this space. In this episode, he discusses how AI is helping us rethink the assembly line of knowledge work and the parallels between AI and the industrial revolution. We also discuss the impact of digital twins and AI administrative assistants with individuals and the law in mind, explore how to train staff on new technologies, and get into the higher-value roles recruiters will need to step into in response to the rise in accessible AI support. Join us for a deep dive into the future of staffing and the legal implications of AI, and the exciting possibilities that await us in this industry.
[0:01:14.4] David Folwell: Hello everyone, thank you for joining us for another episode of The Staffing Show. Today, I am super excited to be joined by Jonathan Kestenbaum, who is the managing director at AMS. Jonathan, really great to have you on the show.
[0:01:27.7] Jonathan Kestenbaum: Thanks for having me, excited to be here.
[0:01:29.4] David Folwell: Yeah, same, same. I’m excited about the conversation. We’re going to be jumping into kind of the future of staffing and talking deeply about AI, some of the legal applications. To kick things off, Jonathan, could you give a little background about who you are and how you got into the staffing industry?
[0:01:44.3] Jonathan Kestenbaum: Yeah. So, I am a licensed attorney by education, but I’ve been an entrepreneur in the work tech space my whole career. I started my career, I built a reverse auction system, which was essentially for tutors. So, students would ask for help, and tutors would bid against each other, ultimately helping students get help at the cheapest price. What I thought I was building at the time was an ed tech company.
I learned pretty quickly I was building a work tech company, helping tutors get jobs. A number of staffing firms on the East Coast were interested in leveraging the reverse auction for their contract staffing business to get higher margins. I ended up selling the company in 2012, and then I met Gene Holtzman, who is the CEO of Mitchell Martin, which is an IT healthcare staffing firm in the New York area.
And we cofounded an organization called Talent Tech Labs, which at the time was meant to be a venture fund to invest in work tech companies, but evolved pretty quickly into a research firm because in an effort to get companies to take us seriously as investors, we would write about trends in work tech, and then we get calls from heads of talent and CEOs and staffing firm saying, “What is this work tech stuff mean to me?”