How To Build Your First Go-to-Market Team with Swing Search
Episode
42 min
Read time
2 min
Topics
Career Growth, Health & Wellness, Startups
AI-Generated Summary
Key Takeaways
- ✓Seniority mistake: Founders typically hire too senior for first go-to-market roles, bringing in VPs who want teams and infrastructure instead of hands-on sellers who can execute tactical work for the next eighteen months and drive immediate revenue without building foundations.
- ✓Timing error: Hiring go-to-market talent before achieving product-market fit creates an oil-and-water problem where sales skills become orthogonal to product discovery needs. Founders should stay in sales themselves until customer conversations consistently validate the product and buying motion.
- ✓Metrics test: Strong sales candidates know exact performance numbers like ranking third with 112.2% quota attainment, not vague statements about exceeding goals. This specificity reveals both competitive drive and intellectual discipline required for the 80% process-repetition nature of sales execution.
- ✓Two-AE strategy: Hiring two founding account executives simultaneously instead of one provides trenches companionship, creates healthy competition, and protects against single-hire failure risk. Hire complementary spikes covering different verticals or deal complexities to fill multiple gaps at once.
What It Covers
Magna Sundstrom and Debbie Whistle from Swing Search explain how early-stage founders should build their first go-to-market teams, covering when to hire, what roles to prioritize, and how to avoid common hiring mistakes.
Key Questions Answered
- •Seniority mistake: Founders typically hire too senior for first go-to-market roles, bringing in VPs who want teams and infrastructure instead of hands-on sellers who can execute tactical work for the next eighteen months and drive immediate revenue without building foundations.
- •Timing error: Hiring go-to-market talent before achieving product-market fit creates an oil-and-water problem where sales skills become orthogonal to product discovery needs. Founders should stay in sales themselves until customer conversations consistently validate the product and buying motion.
- •Metrics test: Strong sales candidates know exact performance numbers like ranking third with 112.2% quota attainment, not vague statements about exceeding goals. This specificity reveals both competitive drive and intellectual discipline required for the 80% process-repetition nature of sales execution.
- •Two-AE strategy: Hiring two founding account executives simultaneously instead of one provides trenches companionship, creates healthy competition, and protects against single-hire failure risk. Hire complementary spikes covering different verticals or deal complexities to fill multiple gaps at once.
Notable Moment
A CEO running a company with over one hundred million dollars in annual recurring revenue apologized for being late to a recruiting call because a sales call ran long, demonstrating that founders never stop selling regardless of company scale.
Episode Transcript
Hey, everybody. This is Ben Kesnoka, cofounder and partner at Village Global, a network driven venture firm. And this is our podcast where we go deep on all things business and technology with world leading experts. Welcome to our master class on building your go to market team. I'm Lindsay, a partner in Village Global. I'm joined today by two absolute maestros, Magna Sundstrom, who's a senior partner at SwingSearch, and Debbie Whistle, a president at SwingSearch. For nearly twenty years, they've specialized in go to market roles at the director, head of, and VP levels, the hires that really matter the most to scaling companies like all of yours. They've worked with several village global portfolio companies, including Multiverse, Growth Therapy, Mosaic Tech, Soarer Schools, and they're currently partnering with MetaView and Alembic. Let's get this started. Magna, what's one mistake that you are 99% sure founders will make with their go to market team? I'll start by saying mistakes will be made. Right? You'll hear me say this again, and I'll hit this note a lot. Perfection is the enemy of progress. And so what we really wanna focus on is progress. But the mistake that I see most founders make is when they're hiring those first go to market or early go to market members on their team, whether marketing sales, whatever the role is, they really default to going to senior. Yeah. It makes a ton of sense, right, because there's so much to get done. And oftentimes, you know, you're looking at mountains, and you wanna see somebody who can see over the mountain. But what I always like to say is, like, let's look for somebody who can see around corners, not necessarily over the mountain. And so you wanna bring that that profile down to somebody who can do the tactical takeaway work that you need over the next eighteen months. And so that's really where I see that mistake made is going to senior too many reps under their belt. Yeah. That's generally what I see. And it makes sense. Right? I think from a founder's perspective, you don't wanna miss. And so you aim really high assuming that this person has done all of this work before. They'll clearly get it done for me, but there's a disconnect there. Can you talk at all about what that disconnect looks like when you do hire the person who can see over the mountains? How do they overcorrect? What are some things you say? There's really two things that happen. You bring somebody in who's, let's say, hands on seller. Somebody's gonna come in, just drive revenue, execute deals, run and go. You bring in a VP of sales instead. Somebody who's been there, has seen the reps, has managed large teams. They're gonna ask for two things. And so they're gonna immediately ask for a team underneath them to do that tactical work. Early stage, cash is king. And so we wanna …
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