Clifton Jadoo has spent the last decade inside some recognizable startups like Hinge, Webflow, Wingspan, Foursquare, Compass. He’s a baller tech recruiter but operates as a People and Talent leader, Talent Management operator as well. He’s sharp, thoughtful, and honest about what’s actually changing in the craft right now. I appreciate just how down to earth and pragmatic he is whenever we catch up.
Cliff is also just a positive guy. I love meeting other optimists in recruiters. It should be fun.
In this episode we talk about how AI is reshaping recruiting workflows without replacing the fundamentals. Clifton and I get into where AI really helps, where it falls short, and why the human layer is still the differentiator no tool can replicate.
Some notes on what to expect:
• Why AI feels overhyped in some areas and underrated in others
• The 85 percent problem and why recruiters still own the final read
• How Clifton builds custom GPTs to accelerate job descriptions, interview banks, and research
• Where research speed becomes a superpower in sourcing
• Why context, judgment, and market awareness still beat automation
• The recruiter as a relationship builder, not a data pusher
• How agency training builds grit, resilience, and resourcefulness
• Managing up with hiring managers and pushing back with data
• Reading resumes in a market defined by layoffs, short stints, and sabbaticals
• Why great recruiting is a business process, not a job title
• How social skills, empathy, and follow-through are becoming differentiators in a noisy market
• The future of office vs. remote through the eyes of New York candidates
• Why Clifton believes trust, curiosity, and storytelling will outlast any tool cycle
Cliff and I have gotten to know each other a bit over the last few years and we definitely relate to the pressure, the pace, the expectations, and the skill sets that will carry recruiters forward in tech startups. You’re the man, Cliff. Thanks for coming on the show.
Connect with him here: https://www.linkedin.com/in/cliffjadoo/
Huge shout-out to our sponsor, Wellfound — where startups and job seekers connect.
From pre-seed to post-IPO, Wellfound is the all-in-one platform to find, connect & hire your team.
Get instant access to a talent pool of 10M+ startup-minded job seekers in seconds.
👉 Try it today
