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

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Apr 4, 2025

Brian Kesselman, co-founder and CRO of Skematic, shares his journey from lawyer to tech entrepreneur in compliance management. He discusses the rapid growth of Skematic within two years, focusing on solving core problems for legal and compliance professionals. Brian emphasizes the importance of proactive sales strategies, customer feedback, and independence in startup culture. He contrasts working in private equity with a family office model, and highlights the successful acquisition of Skematic, reflecting on the pivotal decisions that led to their remarkable success.

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ANECDOTE

From Lawyer to Sales

Brian Kesselman's background is in law, starting at a hedge fund and later JP Morgan.
He transitioned to selling compliance software, leveraging his legal and compliance experience.

ADVICE

Sell Early, Iterate Often

Don't wait for a perfect MVP to start selling.
Sell early versions or prototypes to gather feedback and iterate.

ADVICE

Prioritize Resources

Focus limited resources on essential tools like a database, CRM, and dialer.
Prioritize software development and sales efforts.

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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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