When it comes to hiring, especially in go-to-market roles, like heads of sales, marketing, customer success, one piece of advice Jenny Smith, partner at SwingSearch, recently shared with York IE’s portfolio founders is: don’t overhire too early.
It’s easy to fall for the shiny object: the senior executive with the impressive resume, the big-company background, and the big salary to match. But what often gets overlooked is that these candidates are accustomed to operating with scaffolding: the infrastructure, systems, and teams that support their success. They may never have built anything from scratch. Maybe they’ve never worked without a deal desk or without a full marketing team backing them. Maybe they’ve never had to write their own cold emails, set up their own CRM, or roll up their sleeves and do the hard work of early-stage building.
A common pitfall is hiring your first head of sales before you even have a product marketer with a few years under their belt. That’s a mismatch of needs and expectations. A better approach? Look for what Jenny calls the “hungry number two.”
These are people who have gone through the growth stage you’re about to enter. They’ve worked under a great leader, learned best practices, participated in important decisions—maybe even helped select and implement the tech stack. They’ve touched 70-80% of what you need done and now they’re eager for the chance to own it all. This is their opportunity to step into the number one role.
These candidates are typically more affordable, more motivated, and ready to prove themselves. Of course, there are trade-offs: they might not be as well-known or as skilled at recruiting talent yet. But that’s okay. Everyone in an early-stage company should be recruiting, networking, and evangelizing.
The key is to look for candidates who understand the opportunity, who’ve seen what good looks like, and who are ready to build something of their own. Ask them: what were they hired to do in past roles? Did they see it through? Did they stick around to finish the job or bail for the next shiny thing? Did they learn from mistakes, grow from challenges, and demonstrate the perseverance required to thrive in a startup?
Another tip from Jenny: be honest during the interview process. The best hires are the ones who say, six months in, “There are ten hard things about this job and you told me about nine of them.” No surprises, just aligned expectations and mutual belief in what you’re building together.
It’s okay to hire someone who might not be right for your company five years from now. Hire for the next 12-24 months. Hire the builder who’s aligned with your stage, not the big name who’s built something very different.
Startup success often comes down to timing. The right person at the right moment can change everything.
