Building Your First B2B Sales Pipeline as a Solo Founder
Today’s advice post is by Dan Lesley, Founder of Homestar. Dan has over 20 years building, growing, and selling SaaS tech startups.
Building a B2B sales pipeline solo has been quite the journey. After countless late nights and way too much coffee, I’ve learned to balance product work, support tickets, and sales outreach without completely losing my mind. Through my experience with Homestar CRM in the real estate space, I’ve discovered some hard-won insights about what moves the needle.
I spent my first few months immersed in the real estate world, showing up at open houses and having candid conversations with agents about their daily challenges. Not the glossy marketing survey kind - real talks about what frustrated them most about their current tools and workflows. Those unfiltered discussions shaped Homestar’s core features and messaging.
Understanding our ideal customer profile changed how we approached prospecting. Rather than casting a wide net, I zeroed in on agents who matched specific criteria we knew would benefit most from our solution. Our early prospecting efforts included:
- Use LinkedIn to search for real estate agents.
- Attend industry events and collect business cards.
- Dive into forums and online communities where agents hang out.
- Research competitors’ clients to understand their market strategy.
Cold outreach became our primary channel, though it took plenty of refinement to get it right. I learned to ditch the formal sales speak and write emails that addressed their specific pain points. Sometimes a simple “ noticed you’re using [competitor] - ran into any issues with their contact sync?” opened more doors than any polished pitch.
The follow-up process was honestly uncomfortable at first. Nobody wants to feel like they’re pestering prospects. But data showed most of our closes came after 5-7 touches, so I developed a follow-up system that felt natural. Quick check-ins referencing previous conversations worked better than generic “just checking in” messages.
I tracked everything in Homestar (eating our own dog food). Having a clear view of every interaction helped identify patterns in what resonated with different segments. The data revealed some surprising insights - features we thought were major selling points often weren’t what closed deals.
Customer feedback shaped both our sales approach and product roadmap. When multiple prospects mentioned struggling with the same workflow, we’d adjust our solution so. Some of our most popular features came directly from casual conversations during demos.
Eventually, I incorporated automation tools to handle repetitive tasks, but always maintained that personal touch in key interactions. The goal was to scale efficiently without losing the relationship-building aspect that drove our early success.
Looking back, consistency and iteration were more valuable than any “growth hacks.” Understanding our customers deeply, targeting intentionally, and maintaining genuine engagement through the sales process created sustainable growth. Still learning and refining, but those fundamentals haven’t steered me wrong yet.
Remember that each interaction teaches you something valuable about your market and product. No shortcuts exist, but staying focused on delivering real value while continuously improving your process builds something lasting.