He spent nearly three-quarters of his $16M in funding.
Not on bad hires. Not on a failed product. But on the wrong go-to-market playbook.
In the latest episode of Scaling Without Breaking, I sat down with Neil Cresswell, Founder & CEO of Portainer, who openly shares how chasing product-led growth in a market that didn’t buy that way nearly derailed his company.
Investors wanted PLG. The market needed enterprise sales.
And when you’re selling mission-critical infrastructure software, engineers don’t just swipe a credit card and hope for the best.
Neil finally pivoted: • Shifted from small $7K deals to true enterprise sales • Replaced transactional salespeople with engineers in pre-sales • Re-centered around founder-led sales • Raised prices • Doubled revenue within 12 months
We also unpack: • Why founders get out of sales too early (and why that’s dangerous) • The cost of being stuck in the “dead zone” of mid-sized deals • How to hire leaders who think like you — without creating tunnel vision • Why churn is more dangerous than missing revenue • How founder mode actually works in practice • And the unexpected hobby that helps Neil unplug (hint: it involves rappelling 2,000 feet underground into abandoned mines)
This is an honest conversation about expensive mistakes, painful pivots, and what it really takes to scale enterprise software.
If you’re building in SaaS, infrastructure, or enterprise tech — this episode will challenge how you think about go-to-market.
👍 Like if this changed how you think about founder-led sales 🔔 Follow for more honest conversations about scaling 💬 Comment with your biggest takeaway 🔗 Share this with a founder who needs to hear this
#ScalingWithoutBreaking #FounderLedSales #StartupLeadership #EnterpriseSales #SaaS #GoToMarket #FounderMode #BusinessGrowth
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