Cailean Bailey is a founding recruiter who never stepped away from the work. In this episode, we talk about what it actually takes to build recruiting inside early-stage companies and why the foundation you set early quietly determines whether a startup scales or breaks.
We get into why the founding recruiter role is finally being taken seriously, why great recruiting leaders still carry reqs, and why recruiting is a business process first, not a job title. Cailean shares how credibility is earned by staying close to execution, how candidates pick up on authenticity immediately, and why curiosity beats scripts every time.
We also unpack candidate experience beyond buzzwords. From reducing interview anxiety to building real trust, this conversation reframes recruiting as a long-term relationship game. We talk about return on relationship, why candidates who don’t get hired but still refer others are one of the strongest signals of success, and how intuition and data work together in high-stakes hiring.
If you care about startup hiring, early-stage recruiting, or becoming a true talent partner instead of a transactional recruiter, this episode will resonate.
Episode 017 of Building the Talent Machine drops soon 🔊
Follow Cailean here: https://www.linkedin.com/in/caileanbailey/
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Special thanks to our sponsor, Grayscale. The AI Assistant for all your hiring needs. Grayscale helps you move fast, automate the busywork, and deliver an exceptional candidate experience, all from inside your ATS.
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🎧 Hear more from Grasycale’s founder, Ty Abernethy
