I’ve been in the room when the first deal closed.
I’ve also been in the room when the first salesperson was let go.
And again when the next one was let go, too.
Same product. Same company. Same mistakes.
After 20+ years leading revenue teams as VP Sales, CRO, and now as a GTM Board Advisor to early-stage startups, I can tell you with confidence:
Most sales problems at startups aren’t really sales problems.
They’re go-to-market design failures.
And they’re expensive.
Here are the 7 deadly mistakes I’ve seen (and felt):
1. No clear ICP — selling to whoever shows interest
You can’t grow if you don’t know exactly who you’re solving for. “Anyone who bites” is not a strategy.
2. Misalignment between ICP, product, and GTM motion
You’ve built a product for enterprise but hired a team that knows how to sell to SMB. You’re doing outbound when your buyer prefers referrals. Strategy and execution are playing different games.
3. Chasing low-hanging fruit
Early-stage teams often go after immature companies because they’re easy to access. But those customers don’t stick, can’t expand, and drain resources.
4. First sales hire = lone wolf
You drop a seller into chaos without enablement, messaging, or clear targets. Then expect them to “scale.” It’s not fair to them—or to you.
5. Firing sales without fixing the root cause
Swapping reps without fixing ICP, pitch, motion, or process is like changing tires on a car with no engine.
6. Burning through seed money before validating repeatability
The most dangerous phase is when you’ve raised enough to look busy but haven’t earned real signal yet. Money hides the mess—for a while.
7. Not bringing in GTM expertise early enough
Founders are brilliant builders. But GTM is its own craft. You don’t need more opinions—you need someone who’s done this before and knows where to shine the light.
💡 Here's what I’ve learned:
GTM isn’t magic.
It’s not hustle.
It’s a system.
A system that starts with defining who you're selling to, how they buy, and what real success looks like—and only then scaling it.
If you're a founder feeling stuck in early sales, or a VC watching portfolio burn without results, I’d love to help.
I partner with early-stage companies to build the GTM foundations before the chaos compounds:
✅ ICP clarity
✅ Messaging that resonates
✅ Pipeline models that reverse from targets
✅ Coaching and team building
✅ Alignment across sales, marketing, and product
📩 DM me or comment below if this hits close to home.
You're not alone. And it’s fixable.