Cailean Bailey is a founding recruiter who never stepped away from the work. He’s also become a friend this year. When we caught up in conversation, we dug into what it actually takes to build recruiting functions inside early-stage companies since that’s both of our wheelhouses. We spoke about why the foundation you set early quietly determines whether a company scales cleanly or spends years undoing mistakes. And got a bit honest about how gritty and messy things can be when you’re building a function as a team of one inside tech startups.
We talk about why “founding recruiter” is an interesting job title, why it is one of the most leveraged roles in a startup, and why the best recruiting leaders should still carry reqs no matter their title. We anchored to why credibility with both candidates and hiring managers comes from staying close to execution. Something he and I do because we just like to recruit. It’s not about the title for us. And in a world of self-aggrandizing and over inflation of impact, recruiting leaders can get swept up in corporate jargon and bureaucracy, org chart politics, reporting lines, and centering themselves in the business function. The reality is recruiting is pretty simple. It’s humble work. Don’t take yourself too seriously. Even if you work at a sexy tech company. You’re still just a recruiter.
He and I are also pretty well aligned on delivering candidate experiences that go beyond surface-level tactics. We unpack how curiosity, excitement, and genuine interest in what’s being built shape candidate trust, reduce anxiety, and create better outcomes on both sides of the table. Cailean introduced a cool concept which he brands the “Return on Relationship” and explains why candidates who don’t get hired but still refer others are one of the strongest signals of recruiting effectiveness. Just ask anyone who has worked a req. This happens a ton and is under utilized by most. Especially teams that just rely on inbound.
We bro’d out a bit since we have similar life experiences, and explored how lessons from our time as NCAA athletes, creativity, and team dynamics translate directly into hiring. From character assessment and creative competencies to quality of slate and intuition, we really just want to make the case for recruiters to operate as true talent partners instead of transactional admins.
I’m stoked Cailean is also committed to building teams the human way, staying grounded in the work, and creating recruiting systems that actually hold up as companies grow.
Timestamps
00:00 – Why the founding recruiter role matters
How early-stage recruiting foundations shape company culture, performance, and long-term scalability
03:30 – Recruiting as infrastructure
Why interview loops, intake discipline, and hiring standards quietly define how companies operate
05:00 – Business process first, job title second
Why staying close to the work is critical for credibility as a recruiting leader
06:45 – Strategy and execution in early-stage recruiting
Balancing board-level planning with hands-on sourcing, screening, and closing
08:30 – Candidates feel authenticity
How genuine excitement, EQ, and belief in the product change candidate conversations
10:45 – Lessons from athletic recruiting
What elite sports teach us about character, drive, and long-term performance
13:00 – Hiring for behavior, not just skill
Why the mental and motivational side of candidates matters more than pedigree
15:30 – Seeing candidates as whole people
How creativity, interests, and motivations show up in work and hiring decisions
17:45 – Creative competencies and assessment
Using better questions to uncover curiosity, learning mindset, and adaptability
20:00 – Building hiring team experience
Why recruiters should optimize for hiring managers, not just candidates
22:00 – Representing the “what you’re building” story
How early-stage recruiters sell the work itself, not just compensation or perks
24:00 – Return on relationship
Why long-term trust with candidates compounds even when they are not hired
27:00 – Reducing candidate anxiety
How small human moments create comfort, trust, and better interviews
29:30 – Quality of hire vs quality of relationship
What metrics actually matter in early-stage recruiting
32:00 – Candidates who refer others after rejection
Why this is one of the strongest signals of recruiting effectiveness
34:30 – Intuition, data, and the X-factor
When recruiters need to trust their judgment and challenge hiring managers
37:00 – Breaking the script on “perfect backgrounds”
Why unconventional candidates often outperform traditional profiles
39:00 – What it means to be a true talent partner
Moving from transaction-based recruiting to long-term team building
Episode 017 of Building the Talent Machine is out now 🔊
Follow Cailean here: https://www.linkedin.com/in/caileanbailey/
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