I sat down with Steven Bartel, co-founder and CEO of Gem, to go deep on what really works when you’re making the very first critical hires in a startup. As a builder and operator, I know how much early talent decisions determine product velocity, culture, and ultimately whether the team can execute founder-led GTM with confidence.
Before building the talent acquisition platform, Steven was an early engineer at Dropbox, where he spent 5 years working on analytics, Dropbox Paper, and hiring as the company grew from 25 to 1500 people.
This experience from Dropbox, combined with his lessons from building out Gem’s own team and talking to his customer base of recruiters makes Steven the perfect person to talk to about early-stage recruiting.
In our conversation we focus on how to make those fourth, fifth, or tenth hires — those really early days when your startup has zero brand recognition or recruiting help. Here’s a preview of his tactical advice, paired with my product leadership lens on what to actually do next.
A trick for sourcing second-degree network connections. I’ve used this same approach to turn lukewarm interest into warm intros by mapping mutual connectors across former teammates, investors, advisors, and early customers. The goal is to engineer serendipity: stack-rank warm paths, ask for specific intros, and close the loop quickly with crisp role requirements and a two-sentence value proposition.
The power of sending a “break-up” message in your candidate outreach. When a candidate goes quiet, a polite, time-bounded note that gives them an easy out often re-engages the conversation. It respects their time, signals high standards, and creates a natural moment for them to opt back in—very similar to enterprise follow-ups in founder-led sales.
How Gem brought candidates on to work with them in very structured trial periods before making a full-time offer. I’ve found structured trials invaluable for de-risking early hires: define a scoped project, align on success criteria, and ensure tight feedback loops. This mirrors a product discovery sprint—short, measurable, and collaborative—while giving both sides a realistic preview of working together.
Advice for working on your recruiting pitch and nurturing passive talent. Your pitch should evolve like your product narrative: lead with the mission, the unique wedge, and the precise problems a candidate will own in the next 90 days. For passive talent, sequence lightweight touchpoints (demo the product, share a customer story, invite a technical deep dive) to build trust long before you ask for a decision.
The similarities between early-stage hiring and founder-led sales. Both require targeted prospecting, tight messaging, and rigorous follow-through. The best founders and product leaders treat recruiting pipelines like revenue pipelines—measure response rates, iterate on messaging, and run structured, time-boxed cycles to convert high-signal candidates.
If you’re navigating your first hiring wave, these principles will help you build a repeatable recruiting engine: amplify second-degree networks, use respectful “break-up” nudges, validate fit with structured trials, sharpen your pitch for passive talent, and apply founder-led sales discipline to every stage of the funnel. Do this well, and your early team becomes a durable competitive advantage.
Inspired by this post on First Round.
Leave a Reply