Is your founder guilty? Are YOU the guilty founder? Let’s be honest – all founders commit these sales crimes. The only question is: how many are YOU guilty of?
When I first wrote about the Top 16 Crimes Founders Commit When Transitioning From Founder-Led Sales, I had no idea how many more transgressions I’d uncover. Turns out, the rap sheet is much longer.
My hypothesis remains unchanged: Founder led sales is critical to the success of any new start up. However, every founder is guilty of at least 51% of these sales atrocities. Your employees would convict you in a heartbeat if they served on your jury. And frankly, your opinion doesn’t matter – you’re biased because your mom told you that you’re special.
The Indictment List
So, you’re doing founder led sales. You’ve got what, 10, maybe 20 clients and you think you’re ready to scale? Well, maybe you are, and maybe you aren’t. Let’s see how this goes for you.
30. GUILTY! You believe hiring that fancy sales leader from BigCorp (who’s never actually built a process or team from scratch) is your golden ticket.
29. GUILTY! You’re delusional about equity – thinking a microscopic sliver of ownership and some distant IPO fantasy will hypnotize top talent into working 80-hour weeks. This isn’t founder led sales, this is indentured servitude.
28. GUILTY! Your expectations are divorced from reality – believing sales reps should ramp in two weeks and turn profitable within 30 days on a $100K ACV product. This isn’t founder led sales, this is called smoking hope-i-um.
27. GUILTY! You demand forecasts to be crystal ball accurate, 100% of the time.
26. GUILTY! You claim to treat employees “like family” – but forget you’re actually the crazy uncle we tolerate for exactly four hours at Thanksgiving before we’ve had enough until next year.
25. GUILTY! You believe that hiring a hotshot AE with a list of previous clients will magically bring immediate business. Spoiler alert: it rarely brings ANY business.
24. GUILTY! You think you’re being fiscally responsible by keeping VC money in the bank while forcing your team to do everything manually. This isn’t founder led sales, this is simply stupidity.
23. GUILTY! You obsess over building the perfect CRM sales process before you even have 20 customers. This isn’t founder led sales, this is indication you are a micro-manager.
22. GUILTY! You think you’re ready to go up market with 15 SMB or MM customers and maybe 1 Enterprise logo. This isn’t founder led sales, this is ego led sales.
21. GUILTY! You fail to recognize your founder title opens doors that regular sales titles simply can’t.
20. GUILTY! You don’t understand delegation means actually LETTING GO, not continuously jumping back in because you think you’re the Virgin Mary and created this company through immaculate conception.
19. GUILTY! You believe your horizontal solution should target every vertical simultaneously instead of dominating 2-3 key verticals early-on. This isn’t founder led sales, this is ego and greedy led sales.
18. GUILTY! You refuse to accept that sales will never, ever move as fast as your fantasies suggest. Your projections are hallucinations with Excel formulas.
17. GUILTY! You think you’re the exception to rule #18. You’re not. Direct that energy elsewhere.
16. GUILTY! You read one sales book over a weekend and suddenly think you created the 4-Week NEAT Selling Program. Hint, you didn’t, I did.
The Value Proposition Crimes
15. GUILTY! Your value prop focuses on what you DO, not what PAINS you SOLVE. Nobody buys words, they buy pictures. You gotta Bob Ross this stuff through storytelling. When I say “Tylenol,” you don’t picture a white pill – you visualize someone clutching their throbbing red forehead (the same red as the bottle, by the way).
14. GUILTY! Your value prop reflects what YOU think it should be, not what customers tell you. When’s the last time you asked clients why they purchased and then actually used their words in another discovery call?
13. GUILTY! Your value prop relies on meaningless buzzwords: Effective, Efficient, Fast, AI-powered, World-Class. Newsflash: your competitors use identical language. That’s not founder led sales, that’s copy cat selling.
12. GUILTY! Your value prop lacks concrete examples. It should always follow with “…and this is good because [insert specific use case that makes prospects nod in recognition].”
The Team Building Felonies
11. GUILTY! You underestimate how EXPENSIVE building a revenue team truly is. SDRs, AEs, CS, Account Management – it all adds up fast.
10. GUILTY! You hire salespeople one at a time because you think that’s better for your budget. That’s not founder led sales, that’s stingy led leadership.
9. GUILTY! You hire Sales Operations and Revenue Operations too late. They should come first alongside your Head of Sales.
8. GUILTY! Your AE count exceeds your SDR count – another red flag you’re guilty of most crimes here.
7. GUILTY! You keep new reps chained to their desks instead of meeting clients to truly understand the value your solution delivers.
6. GUILTY! You haven’t documented your success stories beyond Zoom recordings. Where are the transcribed, digestible versions?
The Capital Crimes
5. GUILTY! You obediently follow VC advice about needing “someone who’s done it before.” Here’s the truth: hire for “can do” versus “has done.” Look for hustle, grit, and that chip on the shoulder.
4. GUILTY! You treat sales teams as disposable while giving product teams an endless runway for missed deadlines and marketing teams forgiveness for missed lead goals.
3. GUILTY! You expect VCs to provide this guidance when most haven’t been in the trenches for years. Not their fault – just reality.
2. GUILTY! You undermine your sales team by caving on discounts after deadlines, then blame them – despite never giving them negotiation training on pricing strategy or negotiation tactics.
1. GUILTY! You’re panicking because you now realize you’re guilty of 70% of these crimes, not just the hypothesized 51%.
If you or someone you know may be guilty of these crimes please contact us directly so we can hopefully reduce your bail.
