Bob Pulver talks with Dan Chait, CEO and co-founder of Greenhouse, about how technology, especially AI, is reshaping the hiring landscape — for better and worse. Dan shares Greenhouse’s origin story and the company’s mission to help every organization become great at hiring through structured, data-driven, and fair processes. Together, they explore the “AI doom loop” of automated applications and AI-written job descriptions, the tension between efficiency and authenticity, and how innovations like Real Talent and Dream Job aim to bring trust, fairness, and humanity back into hiring. The conversation also touches on identity verification, prompt injection risks, AI ethics, and the evolving skills that will define the workforce of the future. Keywords AI hiring, structured hiring, recruiting technology, Greenhouse, Real Talent, Dream Job, hiring fairness, candidate experience, identity verification, deepfakes, AI doom loop, prompt injection, job seeker experience, future of work, skills-based hiring, authenticity in hiring, mission-driven leadership, HR tech Takeaways AI can enhance hiring but must not replace human connection and judgment. The “AI doom loop” is eroding trust between employers and candidates. Real Talent helps companies identify legitimate, high-intent applicants. Dream Job empowers real people to rise above automated applications. Employers should be transparent about how AI is used in hiring decisions if they want to build trust while improving their employer brand. The résumé’s role is fading as new ways of showcasing skills emerge. The future of hiring belongs to organizations that unite data, empathy, and trust. Quotes “Our mission is to help every company be great at hiring — and that means putting structure and fairness at the center.” “We’re caught in an AI doom loop where both sides are using automation to outsmart the other — and no one’s winning.” “You can’t automate authenticity. The human element is what stands out most in a world full of AI slop.” “We can do anything, but we can’t do everything. So we focus on what matters most: helping people connect in meaningful ways.” “It’s not about banning AI — it’s about setting clear expectations for how to use it responsibly.” “The death of the résumé has been predicted for decades, but maybe this is finally the time.” Chapters 00:00 – Welcome and introduction 00:44 – Greenhouse origin story and mission 02:50 – Lessons from Dan’s early career and the importance of structured hiring 06:00 – Hiring for skills and potential over pedigree 08:20 – How structured interviews and scorecards create fairness and better data 11:00 – Balancing mission and business success at Greenhouse 13:40 – Introducing Real Talent and solving the “AI doom loop” 16:50 – Detecting fraud, misrepresentation, and risk in job applications 18:45 – Partnership with Clear for verified identities 20:00 – Digital credentialing and transparency in hiring 22:30 – The “AI vs. AI” challenge: automation on both sides of the hiring equation 25:00 – Dream Job: Human intent meets AI efficiency 27:50 – The candidate experience crisis and how to fix it 30:20 – Why resumes and job descriptions are losing meaning 32:00 – Bringing humanity back to hiring in an AI-dominated world 34:30 – The future of the HR tech ecosystem and partnerships 40:00 – Agentic AI and the next frontier of recruiting technology 43:00 – The death of the résumé and what replaces it 47:00 – Skills, AI literacy, and the next generation of workers 52:00 – Setting clear expectations for AI use in hiring 55:00 – Personal AI use: augmenting human connection 56:00 – Closing thoughts and reflections Dan Chait: https://www.linkedin.com/in/dhchait Greenhouse: https://greenhouse.com For advisory work and marketing inquiries: Bob Pulver:⁠⁠ ⁠https://linkedin.com/in/bobpulver⁠⁠⁠ Elevate Your AIQ:⁠⁠ ⁠https://elevateyouraiq.com⁠⁠⁠ Substack: ⁠https://elevateyouraiq.substack.com⁠