The Relationship Hire
A founder just spent 8 months courting a VP of Sales. The lesson isn't that great hires take forever. It's that the best ones start with a relationship.
In the announcement, the founder wrote: "I first met him in 2025 and spent the next 8 months courting him to join us." They did the work of building that relationship from scratch, and it paid off.
But here's what I'd tell any founder reading that post and wondering whether they have eight months to spare: you shouldn't have to start from zero. Relationship-building is essential. Doing all of it yourself, from a cold start, is not.
1. The best candidates aren't looking.
The executive in that post had spent years at Citi and Stripe, where he grew from account executive into the leader the company tapped whenever it needed to build something new. People like that aren't refreshing job boards. They're busy winning, and their current employer works hard to keep them.
That's why a great GTM hire rarely starts as a transaction. It starts as a relationship, often one that began well before either side was thinking about a move. Founders who treat recruiting as "post the role, review the applicants, make an offer" will mostly meet the people who are available, and those are rarely the people who are exceptional.
2. Motion fit beats industry knowledge.
On paper, he looks like an industry hire: years spent selling to the office of the CFO, now joining a company that sells finance software. But what really makes him a fit is the kind of sale he's mastered: complex, high-stakes deals with long cycles, multiple stakeholders, and a buyer who has to be convinced the risk is worth it. That's a very specific motion, and it happens to be exactly the one his new company runs.
We see founders over-index on industry experience all the time ("they were at a competitor, so they'll be great here"). In our experience, industry knowledge can be learned in a few months. In fact, many of the most successful salespeople are naturally curious and energized by the challenge of learning something new to sell. Motion is much harder to learn on the job. A brilliant PLG leader can struggle in a top-down enterprise sale, and someone who's spent a career closing seven-figure deals may not know how to build a high-velocity inbound engine. So the better questions are: what's my deal size, how long is my sales cycle, who's in the room when the deal closes, and has this person won in that environment before?
3. Hire the builder, not the maintainer.
Look at what he actually did at Stripe: led the push into enterprise, helped scale a business line toward $1B, and built an AI-native segment from nothing. That's a builder's track record.
Early-stage companies don't need someone to optimize a mature machine. They need someone who has walked into a blank page and come out with a repeatable motion. When we assess sales leaders, zero-to-one and one-to-ten experience is one of the first things we pressure-test, because leading at scale and building for scale are different skills.
4. The quiet trait that matters most.
My favorite part of the post wasn't about revenue at all. The founder described him as analytical, down to earth, and "the type of leader who always lets everyone else shine."
That trait rarely shows up on a resume and almost always determines whether a sales leader succeeds. The best VPs of Sales we've placed aren't the loudest people in the room. They build teams people want to join, make their reps better, and stay out of the spotlight so the people doing the work can step into it.
Business is a team sport. Great leaders know their success came from their own skill and effort, and also from their teams, their cross-functional partners, market tailwinds, and the competitive landscape at the time. I look for leaders who see that bigger picture, rather than the ones who tell their story as if they did it all alone.
At an early-stage company, where your first sales leader sets the culture for every hire after them, that self-awareness matters even more. It's also exactly the kind of thing you only learn about someone over time, through real conversations rather than a single interview loop.
5. The courting can start before you need it, and it doesn't have to start with you.
That founder's eight months were well spent, but much of that time went into finding the right person and earning their trust from a cold start. That's the part a good search partner should already have underway.
At Will Reed, we spend our days in ongoing conversations with GTM leaders who aren't on the market. We learn what they've built, which buyers they know, what kind of company and founder would actually move them, and when the timing might be right.
So how do we know these people? Many of us came to search after years as operators at companies like Box, Square, Brex, Flexport, Mural, and Google, where we worked alongside a tremendous pool of exceptional GTM talent. Some of our strongest relationships started there: shipping a launch together, pushing through a hard quarter, figuring out a new market with no playbook. That builds a different kind of trust than you get over coffee as a recruiter, and it tends to last.
Those networks grew quickly as our former colleagues went on to become standout leaders at companies like Databricks, Segment, Snowflake, and Looker. They’re now moving to leading AI natives like OpenAI, Anthropic, Cognition, Lovable, Legora, Clay, and many more. Through them, we know their colleagues too. That means warm introductions, and it also means an insider's view of who was truly great, who really moved the needle, and who was along for the ride. That last part is something you'll never find on a LinkedIn profile. As I like to say, “game recognizes game”.
So when a founder calls us, we usually already have a few people in mind. Often they're people we know well, who are open to the right conversation, and who've heard a credible, honest version of the opportunity before the first meeting.
The founder still matters enormously. Top candidates want to know who they'll be building with, and no one can tell your story like you can. But your time should go into the conversations only you can have, rather than months of cold outreach to get there.
The takeaway
If you're starting to think about your next sales leader, even if it's a year out, call me. That's exactly the right time to start the conversation.
Will Reed partners with founders and investors to place GTM executives at seed through Series C companies across AI-native, vertical SaaS, fintech, cybersecurity, and healthcare tech. If you're thinking about your next sales leader, we'd love to talk, and we may already know who you should meet.
