Confessions of a Fractional VP of Sales
I've been a Fractional VP of Sales for two and a half years now - and trust me, I've seen it all 👀.
I've partnered with over 100 early-stage founders (all sub-€5 M ARR) across Italy, Spain, Germany, the US, and Ireland.
Today, with zero finger-pointing (you know I'm a bold Calabrian nice guy 😅), I'm pulling back the curtain on the three biggest, loudest mistakes I keep encountering.
No founders were harmed in the making of these confessions 😈.
Mistake #1 – Let It Go 👸
Greta's (my 4 y/o) favourite cartoon last year was Frozen. You know the song, right? "Let it go, let it go…" 🎶
Picture this: a founder calls me up, excitement in their voice - they've built a "groundbreaking" solution, have no product-market fit, zero inbound leads, and retention is a joke.
Yet they expect me to wave a magic wand and build a predictable sales process. I've seen this three or four times too many.
Symptom: You're pouring cash into ads, racing after every shiny prospect, but churn is above 30%.
Root Cause: No proof of concept, no early adopters begging for more.
Reality Check: Even the best sales playbook can't resurrect a product customers don't want.
If the product stinks, your sales engine becomes useless.
At that point, my work isn't just hard - it's pointless.
It is better to pivot, iterate, or park it before burning more cash.
Mistake #2 – Papa Don't Preach (Pitch) 📢
"Papa, don't preach…" Madonna said it better than I could! 🎤
We've all been guilty of crafting that "perfect" demo deck, where slide after slide shouts, "Look how awesome we are!"
The problem is that prospects only care about their pain points.
I once worked with a founder who kicked off every conversation by pitching their product. They didn't even ask questions.
They just pitched.
While busy preaching their merits, they never paused to ask, "What keeps you up at night?" and - surprise! - they kept losing deals.
If every call starts with your company stats and every demo is a feature parade, you're wrong, my friend.
Stop making it about you. Make it about them.
Mistake #3 – "Nice to Have" Is Not "Must Have" 🫠
"Nice to Meet Ya" might also be "Nice to Have Ya"
In the last few months alone, I've seen half a dozen AI "agents" for verticals like pet grooming, artisanal cheese distribution, cars, and boats.
All of them with zero competition, trying to address a large untapped TAM? 🤔
Big red flag: it usually means zero demand.
Warning Bell #1: Your roadmap is all "future features" with no immediate ROI.
Warning Bell #2: Demos feel like academic exercises, not tools solving real workflow pain.
Warning Bell #3: Prospects nod politely - "That's cool…" - but never pull out their credit cards.
If your product doesn't address a day-one pain - time wasted, money drained, or anything impactful - it stays on the "nice to have" shelf forever.
Must-have means mission-critical. Anything less is just neat tech.
The Real Takeaways 💪
These confessions aren't just entertaining stories but classic traps business owners - like me - fall into.
But you don't have to be doomed by them:
Kill what's not working. If traction is non-existent after a pilot, park it.
Disqualify fast. A prospect that's not fit wastes everyone's time.
Listen to the flags. Customer feedback, usage metrics, churn rates - these are your early warnings.
Stay emotionally detached. Falling in love with your product makes you blind to its flaws.
I've also witnessed jaw-dropping pivots: startups that went from zero traction to doubling response rates and closing deals in weeks.
That magic happens when you have the guts to slay bad ideas, laser-focus on real pain points, and build solutions people can't live without.
Thanks for sticking with me - your inbox deserves something this honest (and this fun), right? 😉
See you next week, folks!
– Matteo
