How We Landed Our First 10 Enterprise Customers in 180 Days
Today’s advice post is by Dan Lesley, Founder of Homestar. Dan has over 20 years building, growing, and selling SaaS tech startups.
Starting Homestar back in 2021 threw me straight into the deep end. We set an ambitious target - 10 enterprise customers in 6 months. Pretty nuts when I think about it now. Sitting here at my desk (still using that worn-out Herman Miller chair from my last startup), I can finally share the messy reality of how we pulled it off.
We started by nailing down what made Homestar different. The real estate CRM market was crowded, but agents kept telling us how frustrated they were with their existing tools. Lost leads, scattered communications, endless paperwork. These weren’t just bullet points in our pitch deck - they were daily headaches we heard about in every conversation.
My previous startup taught me a painful lesson about perfectionism. This time around, we stripped everything down to basics. Our MVP wasn’t pretty, but it worked. We spent countless coffee meetings with agents who didn’t hold back their opinions. Some feedback stung, but it shaped everything we built.
The enterprise sales meetings were interesting. I’d walk in with my pitch deck, but what really got through to customers was just talking about why we built this thing. Real estate tech is full of solutions looking for problems. We went the other way - started with their problems and built from there.
Getting involved in the real estate community meant a lot of early mornings at industry events. Got pretty good at balancing coffee and business cards. Made some genuine connections at conferences, wrote for industry blogs (even when nobody seemed to read them), and slowly built credibility.
Here’s what worked for us:
- Built detailed profiles of our ideal customers after dozens of conversations
- Crafted messages that spoke directly to their specific challenges
- Focused on building fewer but stronger relationships
- Really listened in meetings instead of just waiting to talk
The feedback from these conversations completely changed our approach. Sometimes what clients thought they wanted wasn’t what they needed.
Some days were rough. Had a particularly bad week in month four when three promising deals fell through. Budget freezes, endless decision loops, ghosting after weeks of talks. But we kept pushing, tweaking our approach, finding new angles.
Partnerships saved us more than once. Found a property management software company that complemented our offering perfectly. Their network opened doors we couldn’t have reached on our own.
The negotiation phase was tricky. Started offering pilot programs instead of trials - sounds small, but it made a huge difference in how enterprise clients perceived the commitment. Had to learn when to stand firm on pricing and when to flex.
Six months flew by. Hit our target with 10 enterprise customers - each one a completely different story. These weren’t just logos on our website; they became partners in improving our product.
Looking back, success came from building real relationships rather than just selling features. Those early customers still email me directly when they need something, and that’s how I want it.