The board wants enterprise logos. Eighteen months and a handful of expensive hires later, the pipeline looks great in the deck and nothing has closed. Every Series A board has had some version of that meeting, usually right after someone says “the pipeline is really building.”
Justin Michael has watched that movie more times than he’d like. He spent 13 years selling in ad tech, MarTech and mobile, ran sales as a VP, and now coaches enterprise sellers at companies including Salesforce, HubSpot, Matterport and Proofpoint. He’s also the author of Tech-Powered Sales and, with Tony Hughes, Combo Prospecting. He joined me on MarTalks to walk through where the “go enterprise” decision goes wrong and what founders and boards should watch instead.
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1. Don’t throw out the motion that got you here
The typical failure, in Justin’s words: the company decides to go enterprise, hires “the guys in suits,” and throws burn rate at the problem. Then it meets a six-to-eighteen-month sales cycle before it has the product-market fit to survive one.
His advice is to keep a mid-market or product-led motion running while you move upmarket, budget for the longer cycle, and invest in outbound that finds accounts already in a buying window rather than waiting for them to show up.
2. Beware the Rolodex
The single biggest hiring mistake Justin sees at Series A and B: paying a very large package for a seller’s “Rolodex,” then watching it fail to pay off. Enterprise deals are decided by committees whose members change mid-deal, and repeatedly asking your network for introductions wears thin fast.
My own addition from the conversation: what does carry over is experience in the same sales motion, the same company size and a similar kind of problem being solved. A logo on a resume is not the same thing as knowing how that buyer actually buys.
3. Hire a VP of Sales before a CRO, and let go
Founders who close the first deals themselves are doing the right thing. Hiring a CRO as one of the first people in the building is usually not. Justin’s view: at seed or Series A, bring in a VP of Sales with meaningful ownership who can grow into the bigger role.
The harder part is the founder letting go. If every deal still runs through the CEO, there’s no engine, just a bottleneck with a very good closer in the middle of it. His Moneyball point lands: you may need three people whose combined strengths add up to what the founder does alone.
4. What an investor should look at in the first 30 minutes
Asked what he’d check before a Series B check gets written, Justin starts with a win analysis: where has this team actually been winning, and why? There’s a reason the company has traction, and reverse-engineering it beats bolting on a brand-new methodology.
His warning is over-reliance on automation. In his experience, most enterprise business is still driven by live conversations, so the question is whether the team is actually talking to humans, not how many sequences it’s running.
5. Use AI for the point of view, not the prose
Justin wrote a book on tech-powered selling and still calls himself “pushing the human thing.” AI is excellent at digesting filings, news and board commentary into a point of view. It is not good at sounding like a person, and executives spot the difference instantly.
His fixes are simple: validate the point of view instead of trusting it, write the way you talk, read it out loud, and test your executive outreach on your own company’s executives first. If your CFO wouldn’t reply to it, their CFO won’t either.
The takeaway for founders and boards
Going enterprise is a go-to-market decision before it’s a hiring decision. Keep what’s working, hire for the motion you’re entering rather than the logos someone has sold to, and judge the team by the conversations it’s having, not the size of the pipeline slide.
Justin has more tactics in the full episode, including his “swarm of bees” approach to finding the right owner inside a large matrixed account. Listen to the full conversation.
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