One question every GTM market plan must answer

The One Question Every GTM Plan Must Answer (But Rarely Does)

When early-stage tech companies show me their go-to-market plan, I ask one simple question: “Can a rep with no industry experience close a deal in 60 days using this story and these tools?” Most founders pause. Then nod. Then—more often than not—they realize the answer is no. That pause is the real test. Because if your GTM motion only works when the founder is in the room, or when the AE is a 20-year industry veteran, it’s not a repeatable strategy. It’s a fragile workaround disguised as momentum. After decades leading GTM teams and helping nearly 40 companies go from early traction to exit, I’ve developed what I call the “60-Day Litmus Test” for evaluating go-to-market strategy. It cuts through hype, slides, and sentiment to reveal if your playbook is actually built to scale. Let’s break it down.

🚦The 60-Day Litmus Test

Ask yourself: Can a freshly hired sales rep, with no industry background, close a deal in 60 days using only the narrative, tools, and process you’ve built? If the answer is yes, congratulations—you’ve operationalized product-market fit into a functioning revenue engine. If the answer is no, don’t panic. But do diagnose.

🛠️ What This Test Reveals

This one question surfaces weaknesses fast. Here’s what it’s really testing: – Narrative clarity – Is the story simple, specific, and sticky? If a rep has to “learn it by shadowing the founder,” it’s not a story. It’s tribal knowledge. – ICP precision – Can a junior rep identify who to call without needing a three-week onboarding on industry jargon? – Enablement & tools – Is your sales motion codified in a way that enables consistency? Can they demo? Handle objections? Get a contract out quickly? – Product readiness – If a deal closes, can the delivery team implement and support it without heroics? Too many early-stage companies build their GTM strategy around unicorn reps and founder-led sales. That may get you from $0 to $1M, but it won’t get you to $10M and beyond.

💡 Best Practices from the Field

Here’s how I help clients build GTM systems that pass the 60-Day Test: 1. Codify your messaging into a single source of truth. One-pagers, demo narratives, objection-handling guides—every company needs them earlier than they think. 2. Instrument your pipeline to flag bottlenecks. If reps are getting stuck at the same stage, it’s not them—it’s your process. 3. Shrink the ICP, don’t expand it. Early-stage founders often try to go broad. The sharper the ICP, the faster new reps find traction. 4. Test with a “cold rep.” Hire a smart, coachable AE with no prior domain experience. If they can’t close quickly, fix the system—not the person. 5. Get out of the founder’s shadow. Build systems that work without you. Your GTM shouldn’t depend on your charisma, network, or ability to jump in late-stage deals.

🔁 GTM is Not a One-Time Strategy

It’s a system. A loop. A series of plays and messages that must be learned, adapted, and refined continuously. The companies that win aren’t the ones with the most slides. They’re the ones that reduce the sales process to something that can be learned, executed, and repeated. The 60-Day Test isn’t about lowering the bar. It’s about designing a GTM motion that doesn’t rely on miracles.

🧠 Closing Thought

Next time you review your go-to-market plan, skip the spreadsheets and ask this:Could someone brand new close a deal in 60 days using this?If the answer is no, fix it before you scale it.If the answer is yes—build the machine and press play.

🚩 Ten Red Flags to Look for Before You Join, Invest In, or Represent a Startup

As someone who has been deep in the trenches of startup life—leading marketing transformations, advising founders, and recovering from a few spectacular crashes—I’ve learned the hard way that due diligence is not just for lawyers and VCs. Whether you’re considering joining a startup, investing in one, or taking it on as a client, these are the top ten red flags I’ve come to recognize. Ignore them at your peril. This isn’t theory. These are patterns I’ve seen play out in real time. Some I caught just in time. Others—like the stories I share in this article on two epic marketing failures—were disasters that could’ve been avoided if someone had asked the right questions sooner.

1. They Say They Have Product-Market Fit, but Can’t Prove It

If they’re claiming rapid growth or “pull from the market,” ask to see renewal rates, customer retention, or even direct references. Often, the early customer base is made up of friends and favors—not actual fit.

2. The Tech Doesn’t Work (Yet They’re Marketing It Anyway)

This one is more common than you’d like to believe. A sexy demo, a polished pitch deck, but no working product. If the “AI” is just a spreadsheet with smoke and mirrors behind it, run.

3. Funding Outpaces Traction

When the raise looks like a Series B but the customer traction looks like pre-seed, you have to wonder: is the company optimizing for PR or solving a real problem?

4. Customer Logos Without Customer Love

Beware the pitch deck adorned with Fortune 500 logos but no case
studies, no quotes, and no repeat revenue. This often signals
non-repeatable, one-off deals used to signal legitimacy.

5. Over-Polished Branding That Obscures the Truth

A beautiful website and killer pitch videos don’t mean the company is real. One of the worst frauds I saw had the best marketing materials. We found out the customer testimonials were fake.

6. Founders Who Won’t Let Go of the Narrative

If the story never changes—no matter what the data says—they’re more interested in preserving the myth than facing the reality. Dogmatic founders can burn millions chasing the wrong market.

7. No External Validation (or Fear of It)

Healthy startups encourage validation: analyst coverage, independent audits, customer interviews. If they resist external scrutiny, they may be hiding something.

8. The Culture Smells Like Chaos

Ask about turnover, especially in marketing, product, and engineering. A revolving door is often a sign of deeper dysfunction—and a management team in denial. Also, and this has affected me several times in my career, make sure there is diversity of relationships on the board and management team. Too often, I find management teams and the founder’s board made up of people with personally close relationships making it nearly impossible for “outsiders” to affect the trajectory of the company. It’s natural to have some previous relationships existing in the company, but be wary of a closed system or “cabals”.

9. Ethical Flexibility Framed as “Founder Hustle”

Be wary when bending the rules is considered a virtue. I’ve seen founders lie to investors, puff their numbers, or fake compliance “just until we close the round.” Don’t hitch your wagon to that.

10. They Want Advisors but Ignore Advice

If you’re being asked to join as an advisor, investor, or board member, but your counsel is routinely ignored, you’re a prop, not a partner. Get out before you’re blamed for the crash.

Final Thoughts

Startups are risky by design—but not all risks are worth taking. If even two or three of these red flags show up, it’s time to ask harder questions or walk away. Trust your instincts, do the work, and never confuse great storytelling for great execution. I’ve done both. One builds real companies. The other builds illusions.

🔍 Bonus: Due Diligence Checklist

Want a 1-page checklist version of this article to use in your next deal or job interview? DM me or leave a comment below, and I’ll send it to you.