#138: Achieved Strategic Acquisition Just 2 Years After Launch - Brian Kesselman

#138: Achieved Strategic Acquisition Just 2 Years After Launch - Brian Kesselman

Author: Greg Head April 4, 2025 Duration: 1:00:15

Brian Kesselman is cofounder and now CRO of Skematic, a compliance management and workflow software for financial services firms. Brian was a lawyer for major financial services companies who helped manage internal compliance in this highly regulated industry. He took a job selling compliance software and broke sales records before starting Skematic with a coworker and launching in September 2022.

Skematic grew quickly by solving an acute problem for lawyers and compliance execs just like him in his industry. The company became profitable quickly as Brian focused on outbound selling with cold calls and savvy demos to busy compliance executives. They grew fast, were profitable in just over a year, and attracted attention from potential acquirers. 

In June 2024, Financial Recovery Technologies, a fintech legal software company, acquired Skematic for an undisclosed amount, including some cash and incentives. Brian and his cofounder still run Skematic and enjoy being part of a bigger software company owned by a private family office that is highly aligned with their culture and values.

Quote from Brian Kesselman, cofounder and CRO of Skematic

"My co-founder Charles and I had worked at a number of PE-backed software companies. And we had our own opinions about what it's like to work at a PE-backed company."

"The family office structure is very different from a private equity firm across the board. They're looking typically to build profitable cash-producing assets. And so that enables our team to think long-term, which benefits not only the founders and the people that are still participating in the upside of the business."

"That also means that the clients will benefit because you are going to do things that will benefit the clients every step of the way, one year, two years, five years, 10 years. And that was paramount to us, given that we've grown up in this very niche industry and our reputations to us are pretty much everything we have."

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Greg Head hosts the Practical Founders Podcast, a series dedicated to the often-overlooked builders in the technology and business landscape. Each week, the conversation focuses squarely on founders who have successfully scaled their software companies through means other than massive venture capital. You'll hear detailed, candid stories about bootstrapping, profitable growth, and the strategic choices that define a sustainable enterprise. These interviews dig into the real work of building a valuable company-the early decisions, the pivotal mistakes, the practical systems, and the personal resilience required. It’s for entrepreneurs and operators who are more interested in durable ownership and practical execution than in hype or fundraising rounds. By focusing on firsthand experiences, this podcast provides a grounded perspective on entrepreneurship. Listeners gain actionable insights and honest reflections from leaders who have navigated the complexities of building a business on their own terms. The discussions are in-depth and specific, offering a valuable resource for anyone looking to understand the tangible realities of creating a technology company without relying on external funding. This is where the conversation moves beyond theory into the applied lessons of proven founders.
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