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Chloe described a shift in how she engaged with prospects, moving away from pitching toward active listening. She framed it as “approaching things from a diagnostic approach, which I personally feel is a much more authentic way of just understanding your customer’s problem.” The goal was to resist the instinct to lead with her own perspective and instead follow the customer’s. “That doctor-patient approach has been really helpful in being able to really listen and actively listen to what the other person is saying instead of trying to be understood first.” Founders who enter sales conversations focused on being understood close fewer deals and learn less about their market. Listening first is both a sales technique and a discovery method.
Tom spent years as a civil engineer and field engineer before founding Civ Robotics, and that background became his primary sales asset. He framed his approach this way: “I don’t look at this as technology. I look at this as a tool and I speak the language as a civil engineer and field engineer that was in their boots literally a few years prior.” That positioning changed the nature of the conversation with buyers: “I can relate to them not as a sales rep, but as an industry colleague and speak their language and talk their pain points [and] that is something invaluable.” Founders who can sell from genuine domain fluency earn credibility that no sales training replicates.
In construction, buyers want to purchase from people who understand their problems, which kept Zach directly involved in sales well past the point where his team could close deals on their own. He stayed embedded through the first couple million in ARR and remained involved as executive support beyond that: “The industry likes to buy from people that understand their problems.” The threshold he identified for founder participation was clear: “Definitely through that first million, I think the founder needs to be on at least one call in every deal.” It was only somewhere between one and two million in ARR that deals started closing without him on the call. In industries where domain credibility drives trust, the founder’s presence in early deals is a sales asset, not a bottleneck to route around.
James and his co-founder personally executed the initial outbound campaign, going straight to the executives who owned development at major retail chains and restaurant groups. “We started cold emailing retailers. We cold emailed all of them, all the ones you can think of, the big restaurant chains, quick service restaurants, the big retailers in general.” The message was a single operational question with no product pitch attached. “When you send someone an email [asking,] are you missing your openings due to permitting? And they respond back, yeah, what do you got for me? That’s kind of magic the first couple times that happened, and that’s how it all started.” Founders who carry the first outbound motion themselves learn faster which message opens doors and which titles actually feel the pain.
SubBase’s outbound motion gained traction because the team could meet prospects on their own terms, with Eric crediting the results to “speaking the language of the contractors that we’re getting in front of.” Rather than leading with a product pitch, the team built their approach around education, recognizing that construction buyers want to understand why software that didn’t exist a few years ago is now worth adopting. Eric connected his own credibility directly to that approach: “I come from the industry. I love speaking about what we’re doing. [That] thought leadership approach has been very helpful.” In markets where buyers are skeptical of outside solutions, fluency in the buyer’s world is what earns the right to educate them in the first place.
Before Dextall had a track record as a company, Aurimas had one as an operator. “The first clients came in because I had some street credibility. I was able to deliver on the large projects. I was able to deliver and execute on very complex projects.” That credibility opened the door, but it did not close the deal on its own. The product still needed to prove itself, so the team started deliberately small: “We started with projects that are [nine] stories, 10 stories, relatively small footprint,” then kept adding from there. Your personal reputation in an industry is a sales asset that exists before your company has earned one of its own. Use it to get in the room, then let small wins build the proof that takes over from there.
Early access to a concentrated list of potential buyers is only useful if you work through it completely. When Anwar and his co-founder landed their first general contractor, it handed them a defined pool to pursue directly: “By selling this piece of software to the large [general] contractor, we got access to 300, 400 subcontractors on the platform. And then we started reaching out to them to highlight our early pay program and see if they were interested.” The outreach was as straightforward as it sounds. “At the beginning, Tony and I would just try to call every single subcontractor on the platform.” When your market is finite and in front of you, work the full list yourself before building anything more elaborate around it.