Asking for a Friend: Should I Be Leading This Team?
Are you a wizard pretending to be a builder?
Fun fact: commercial airline pilots are required to log 1,500 hours of flying time — and that’s just to qualify for one type of aircraft. Want to switch to a different jet? Great, start from scratch.
Meanwhile in Go-To-Market land: “You scaled a SaaS company? Fantastic — now go lead sales in industrial manufacturing.” Because clearly, switching industries is just like switching seats on the same flight… right?
This isn’t another LinkedIn pep talk about impostor syndrome or how feeling “out of your depth” is a beautiful sign of personal growth. No. This is about something more foundational: Are you even remotely qualified to lead your sales team in this industry — or are you just hoping the turbulence goes away?
So I Asked ChatGPT: What Kind of GTM Leader is Needed to Succeed?
Yes, you can outsource a plethora of existential crisis to AI. Productivity win.
First up: What kind of GTM leader thrives in the safety industry?
The answer was alarmingly reasonable: it’s a mature, commoditized industry, where the secret sauce is process discipline, fast response times, and making customers feel like they’re not being ignored. Also, if you manage to upgrade the tech stack beyond “Dave’s Spreadsheet v4,” you’re basically a prophet.
Then I asked the same question for the additive manufacturing industry.
This time, the advice boiled down to: Hire Gandalf.
Apparently, you need someone who can navigate market chaos, sniff out the one promising tech from the dumpster fire of LinkedIn hype posts, and cast spells to convince skeptical buyers to adopt something nobody fully understands yet. Less Six Sigma, more storytelling. Charisma over process. Big vision over consistent execution.
Same job title. Completely different DNA.
We Hire for Culture Fit. We Fire for Personality Mismatch.
We spend hours obsessing over culture fit, industry experience, and the sparkle on someone’s track record. Then someone with a “Top 50 Under 50 While Skydiving” award joins your team… only to crash and burn within 12 months.
Why? Because we hired for pedigree, not sales personality fit.
There’s a brilliant little book called Selling the Wheel by Jeff Cox and Howard Stevens. It breaks down four classic sales archetypes — and once you know them, you’ll start seeing them everywhere.
🚪 The Closer
Lives for: High-stakes, high-velocity sales. Quotas are a love language.
Strengths: Aggressive, decisive, allergic to silence.
Weaknesses: Will absolutely try to close the deal before the prospect finishes saying “Hello.”
🧙 The Wizard
Lives for: Cutting-edge innovation. Selling the dream — even if the product isn’t quite awake yet.
Strengths: Charisma. Vision. Gets customers to buy PowerPoint decks like they’re finished products.
Weaknesses: CRM hygiene is a myth. Follows up… eventually. Maybe.
🏗️ The Builder
Lives for: Building territories from scratch, designing process flows, color-coding their calendar.
Strengths: Reliable, scalable, and low-drama.
Weaknesses: Will spend six weeks planning instead of selling. Chaos gives them hives.
📚 The Researcher
Lives for: Product knowledge, documentation, and fixing the internal mess others leave behind.
Strengths: Knows more about the product than the product team. Actually reads release notes.
Weaknesses: Selling? Oh no, no thank you.
Why This Actually Matters for GTM Leaders
You might think: “We’ll just train them.”
But here’s the thing — these aren’t just skills. These are personalities. You can’t train a marathoner to win the 100-meter dash. You’ll just end up with a tired and frustrated sprinter and no medals.
Same goes for GTM leaders. If your VP of Sales built her career pitching bleeding-edge SaaS with visionary decks and a half-working beta, don’t expect her to dominate in a margin-sensitive market where the buyer wants a quote, not a TED Talk. And vice versa.
Worse — products evolve, and your GTM org needs to evolve with them. The same way CEOs in some industries cycle out every 3–5 years, your sales org might need a different dominant personality depending on your product’s life stage.
There was a time when selling insurance required a Wizard to convince people it wasn’t a scam. Now? Visit a website and you’ll get four voicemails, three emails, and a LinkedIn connect request before you click “quote.” It’s a Closer’s world now.
So… Should You Be Leading This Team
Maybe.
But only if you’re not a Wizard trying to fly a Closer’s plane. Or a Builder stuck in a startup that needs pyrotechnics, not process maps.
Because leadership isn’t just about logging hours and working hard. It’s about knowing whether you’re on the right damn flight in the first place.
The better question isn’t just “Am I good at this?” — it’s: Does your GTM org — from top to bottom — have the right sales personalities for the market you’re in today?
Because if not? No amount of Salesforce dashboards is going to save you from a crash landing.