Digital Reasoning, a buzzy fintech valued at $270 million and backed by Goldman Sachs and Nasdaq, has lost its CEO and a handful of senior executives

Digital Reasoning

Former Digital Reasoning CEO Brett Jackson has left the $270 million AI company.

• Brett Jackson has recently resigned from his role as CEO at fintech Digital Reasoning, Business Insider has learned.
• Digital Reasoning, which is valued at $270 million and backed by Goldman Sachs, Barclays, and Nasdaq, uses AI technology to surveil employee communications to spot potential insider trader or rule-breaking.
• Besides Jackson, four other senior executives have left the buzzy AI firm in the last six months.

The chief executive of Digital Reasoning, a fintech valued at hundreds of millions of dollars and backed some of the biggest banks, resigned earlier this month.

Brett Jackson stepped down as CEO of the AI software firm on February 7, less than two years after joining the company, Business Insider has learned. Jackson departure from the Franklin, Tenn.-based company that is reportedly valued at $270 million is the latest in a long-line of senior departures from the company, whose investors include Goldman Sachs, Credit Suisse, Barclays and Nasdaq, among others.

Jackson departure is the latest exit from a senior Digital Reasoning executive in the last six months. Digital Reasoning's head of North American sales (Jon Flynn), head of product (William DiPietro), and its chief product officer (Marten den Haring) have all departed recently. Digital Reasoning's director of global sales operations (Lisa Smith) is also on her way out, people familiar with the matter told Business Insider.

Jackson did not return multiple requests for comment. The other departing employees either declined to comment or did not respond.

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Founded by Tim Estes and Dot Curry, Digital Reasoning uses machine learning techniques to surveil and analyze different forms of communication to suss out bad behavior. For banks, the software can be used to flag potential instances of insider trader of price fixing among employees. The startup, which also has offerings for healthcare and law enforcement, has raised $104 million, according to Crunchbase.

The recent departures were in part, the result of a culture clash between Jackson and Estes, who serves as president of the firm, according to people familiar with the matter. The decision to hire Jackson as CEO in 2017 was made by Digital Reason's board of directors, which felt more professional management should be brought in. Estes founded the company in 2000 when he was a senior in college and had run it ever since. Jackson, meanwhile, had led a number of tech companies, including analytics firm Logi Analytics and software company Digital Harbor.

Following his appointment, Jackson was tasked with growing the business and bringing on additional staff. Estes, did not always see eye-to-eye with all the changes Jackson was making, the people said.

Estes issued the following statement to Business Insider: "As a rapidly growing technology company, planning for and embracing change is essential and necessary. At Digital Reasoning, we've built the industry's most trusted enterprise AI solution for understanding human communications in financial, law enforcement and healthcare by not standing still. While we are proud of our ongoing and accelerating achievements, we have a strong leadership team and the best is yet to come."

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Digital Reasoning's board of directors is currently in the process of finding a replacement for Jackson, and is considering external candidates, according to sources. In the meantime, Kathy DeKam, Digital Reasoning's chief people officer, and Prakash Ramachandran, its chief financial officer, are handling Jackson's responsibilities, which were largely internal, sources said. DeKam and Ramachandran have both previously held executive roles at other companies prior to joining Digital Reasoning.