Miles Randle has spent his career inside early-stage startups and scaling teams at places like Fractal, Flip CX, and The New York Times. He’s been employee two. He’s built recruiting from zero. He’s moved from pure recruiting into people operations and leadership. And he’s done it the hard way, by actually doing the work instead of hiding behind tools, dashboards, or buzzwords.
Miles is sharp, curious, and deeply pragmatic about what recruiting really is and what it is not. He’s not chasing trends. He’s not trying to be loud. He’s focused on fundamentals, human behavior, and building systems that actually hold up once the hype fades.
What I appreciate most about Miles is how grounded he is. He’s thoughtful about burnout. Honest about incentives. Clear-eyed about AI. And very comfortable saying the quiet part out loud when it comes to how broken recruiting can feel if you stop caring about people.
In this episode, Miles and I talk about recruiting in the middle of the coming AI slop. We unpack why AI is becoming an easy scapegoat for bad sourcing, weak interviewing, and lazy fundamentals. We talk about pattern disruption as the real advantage recruiters still control, and why curiosity beats automation every single time.
Some notes on what to expect:
• Why recruiters are blaming AI instead of fixing broken sourcing and interview fundamentals
• What pattern disruption actually looks like in real outreach, not theory
• Why curiosity is the clearest signal separating good recruiters from great ones
• How early-stage recruiting and people ops are inseparable
• What Miles learned being employee two and building from nothing
• Why recruiting, HR, and people operations can’t be treated as separate silos
• The limits of metrics, dashboards, and predictive people analytics
• Why candidates make decisions on feeling, not just data
• How bias actually works in hiring and why pretending it doesn’t exist is dishonest
• Why AI can make you slower if you don’t understand the job first
• How founders misunderstand when they actually need a recruiter
• Why better hiring solves more problems than better analytics
• What burnout taught Miles about autonomy, curiosity, and staying human at work
• Why recruiting is hard, why that’s okay, and why it still matters
Miles and I also spend time talking about work itself. Not the LinkedIn version. The real version. The kind that’s repetitive, emotional, and often thankless. We talk about why recruiting isn’t for everyone, why that’s fine, and why the people who choose it need to fully own the craft instead of hiding behind process or tools.
This conversation is for recruiters, founders, and operators who feel the noise getting louder and want to remember what actually works. If you care about building teams that last and not just filling seats, this one’s for you.
Miles, thanks for coming on and keeping it real.
Episode 015 of Building the Talent Machine is out now. 🔊
🎧 Listen on Spotify
▶️ Watch on YouTube
Follow Miles here: https://www.linkedin.com/in/milesrandle/
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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, and hire your team. Try it at wellfound.com.
