Bootstrapping Enterprise Software with Rob Kabera, CEO Sheltera
I used to this that any company selling to enterprise needed to raise venture capital. Rob Kabera proved me wrong.
In this chat, Rob shared his story of bootstrapping his enterprise software Sheltera, growing the deal size from a mere $100 to $60K (!) today all while keeping a sales cycle under 6 months.
How’d he do it? By simplifying his product, rapidly experimenting, cutting costs. Oh and, and last but not least, treating his end customers like human beings. Turns out b2b buyers have feelings too.
Probably my favorite of this talk though was at the end. When I asked Rob what he wants more of, he had a clear answer: community.
As the founder of Seeking Solutions Collective, that moment gave me a jolt of energy. I can’t wait to bust more myths, share our stories, and have a few great laughs along the way.
A full recording and transcript of this talk is available for SSC Members.
KEY TAKEAWAYS
Simple isn’t always bad: Robert started off building something super complicated but no one bought it. His breakthrough? switching to vegetation management product was far simpler to build, but crucially even simpler to sell.
Get paid first, build second: Robert’s first customer paid him a mere $100. That was enough though, to prove that someone was willing to pay. Chasing a larger existing budget, the deal sizes quickly ballooned, from $1500 to $10K and now $60K ACV.
Bootstrapper advantage: Not having money meant Sheltera’s tech was built for a fraction of the cost and delivery at a higher speed than VC backed competitors. Lean into what you can do well.
Enterprise buyers are human: Buying decisions are not just financial, they are emotional. Robert used humility to appeal to a buyer that was historically disrespected, and customization to appeal to their bespoke needs versus traditional package offerings.
Run parallel Experiments: Robert figured he had two key experiments to test: Could he shorten sales cycle to under 6 months? And Could he raise the 10x price point. He ran these sequentially but now is now testing “8 new revenue streams in parallel”.
It’s all about cutting costs: It’s easy to make money, but it’s had to keep it. Getting to breakeven was about obsessively cutting costs. For bootstrappers, this is easily almost as important as growing revenue!