At York IE, we know that one of the most critical decisions a founder can make is who they bring onto their team, especially in the early stages of company building. That’s why we were thrilled to host Jenny Smith, a seasoned talent leader, for a conversation with our portfolio founders about how to identify and recruit startup-ready talent.
Jenny brought incredible clarity and nuance to a challenge many startups face: finding the right people to lead core functions like sales and marketing in a high-growth, often ambiguous environment. Below are a few of the key takeaways she shared.
Every Startup is a Revolution
One of Jenny’s guiding principles is that “every startup is revolutionizing something.” By nature, startups are doing things that haven’t been done before – creating new categories, redefining industries, or changing how a problem is solved. That makes it incredibly hard to find someone who has “done this exact thing before.” Instead, the real question becomes: Can this person figure it out in a fast-paced, evolving environment?
Prioritize Learning Agility Over Perfect Experience
Rather than chasing the “safe on paper” candidate, Jenny encourages founders to look for learning agility. Has the candidate successfully taken on challenges in unfamiliar spaces before? Have they demonstrated grit, curiosity, and a willingness to learn fast?
This quality can often be a stronger indicator of success in a startup than a perfect resume. Jenny noted that while adjacent experience is valuable, it’s more important to see if someone has repeatedly shown the ability to step into the unknown and figure things out.
Look for Verbs That Matter
One tactical tip Jenny shared was to listen closely to the language candidates use when they describe their work. Look for action verbs like build, design, solve, or figured out. Then dig deeper:
Who identified the problem?
Who decided it was their responsibility to solve it?
Who did they bring along the journey?
These questions reveal whether a candidate is a self-starter with high agency and a collaborative mindset, which are essential qualities for early-stage hires.
Interviewing is a Two-Way Street
Jenny also highlighted a subtle but important shift: in today’s market, high-quality candidates are interviewing companies just as much as companies are interviewing them. Founders should create space in interviews for real conversations, not just rigid Q&A. Talk shop. Invite candidates to problem-solve with you. Look for curiosity and shared vision.
Align the Role with the Stage
Finally, Jenny warned against one of the most common traps: over-hiring. It can be tempting to chase a big-name candidate introduced by a board member – someone who’s scaled a 50-person team or seen an IPO. But if you’re a Series A startup still figuring out product-market fit, you likely need a player-coach, not a polished executive who’s far removed from the trenches.
Ask candidates early on about their own career criteria. What are they looking for in their next role? Why does going “early-stage” appeal to them? If their only motivation is equity, that’s probably not enough. Look for alignment in scope, motivation, and the willingness to build from the ground up.
At York IE, we’re incredibly grateful to Jenny for sharing her hard-earned wisdom with our community. Her insights remind us that hiring isn’t just about checking boxes. It’s about finding people with the mindset, motivation, and agility to help shape the future.
