September 16, 2025
In this recent master class hosted by the word-renowned VC firm, Village Global, Lindsay Pettingill, Investment Partner, sat down with Magna Sundstrom and Debbie Wissel to discuss one of the most critical decisions a founder makes: hiring the first go-to-market (GTM) leader.
Here are the highlights and key takeaways from the discussion:
Don’t Hire Too Senior, Too Soon
- Your first GTM hire shouldn’t be the person who only wants to build strategy and manage a team. Instead, look for someone who can roll up their sleeves.
- Think up-and-comer — someone who can “see around corners.” A leader who can see over the mountain may be too senior for what you need in the next ~18 months.
- A GTM hire cannot fix a product–market fit issue. That responsibility still sits with the founder and product team.
Process Matters More Than Perfection
- Hiring is about making decisions with incomplete information. At some point, you have to take the leap.
- Use a Missions, Outcomes, and Competencies framework to get clarity on what you’re really hiring for. This exercise can extract more clarity than a typical job description. (Ask SwingSearch for a template! ((link to contact us form))
- Assign someone on the interview team to play the skeptic role so you don’t get swept away by charisma.
- Remember: hiring is never “done.” It’s like laundry or saving money, an ongoing goal and task.
What to Look For in Sellers and Marketers
- Great sellers are often “coin-operated”: motivated by goals and disciplined in execution.
- The bestsellers know their metrics cold — quotas, rankings, conversion rates — and can talk about them with rigor.
- Be clear upfront: are you hiring a growth marketer (analytical, engineer-like) or a product marketer (brand and messaging)? Very few can do both well, so understand what you want their “major” to be.
Tools and Early Stacks
- The GTM tech-stack you choose shapes your pace and progress.
- A great litmus test for candidates: are they curious and experimenting with new tools in life outside of work?
The Founder’s Role in Hiring
- Start by asking: what am I not good at? Your early hires should balance out your weaknesses.
- Early-stage hiring is about potential, not polish. You’re betting on someone’s ability to grow into the role.
- Documentation and training are critical. You can’t delegate expectations that aren’t clear. If you can’t write it down, you can’t delegate it.
- If you’re ready to hire an AE, be prepared to hire two. If you’re hesitant, you may still have a product challenge to solve.
- Thanks to Lindsay, we could improve upon our analogy; SwingSearch acts as a spear, not a fishing net. Engage a retained search firm when the role you need is specific-enough or urgent enough that a catch-all fishing net won’t suffice.
Final Thought
Founders are always recruiting; recruiting investors, customers and talented teams. Get good at the process early; your long-term role will be that of talent magnet.
Would you like us to publish future Founder Session recaps? Let us know and contact us.