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"As the head of risk and finance, I spent most of my time on risk and not a lot on finance because Pilot did such a great job."
Since 2022, Tola has been on a mission to build software and financial products that help the small business economy thrive, and they’ve been with Pilot since the early days. Anyone who’s ever worked at a startup knows that attention and bandwidth are at a premium in a small, fast-moving company. Evan put it this way: “As the head of risk and finance, I spent most of my time on risk and not a lot on finance because of what a great job Pilot did.”
At one point, Tola decided they would do their own books. The difference between working with Pilot and handling it in-house was so stark that they came back, and Evan says he’s “so [expletive] glad we did.”
As someone who sells software, there’s no greater compliment than a boomerang customer.
Evan always had someone to call at Pilot, and he felt like everyone he worked with at Pilot was helpful and responsive. During the acquisition process, his usual point of contact was out of office, and he was able to escalate the issue and have a member of the Pilot team join an important call with all of the parties involved the very next day.
Not only was the day-to-day and month-to-month stuff great, but when push came to shove, Pilot was on the money... It was a great experience.
After three years of operation, Tola was acquired by Square. As part of the acquisition process, Evan handed over the books generated by Pilot. As Evan said, “They had 135 people on our deal. The books stood up to real scrutiny.” As of Fall 2025, Tola has now been folded into Square.
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Tola is a Y Combinator and Sequoia-backed startup focused on helping businesses across the U.S. manage their cash flow with more confidence. It was acquired by Square in 2025.
Since 2022, Tola has been on a mission to build software and financial products that help the small business economy thrive, and they’ve been with Pilot since the early days. Anyone who’s ever worked at a startup knows that attention and bandwidth are at a premium in a small, fast-moving company. Evan put it this way: “As the head of risk and finance, I spent most of my time on risk and not a lot on finance because of what a great job Pilot did.”
At one point, Tola decided they would do their own books. The difference between working with Pilot and handling it in-house was so stark that they came back, and Evan says he’s “so [expletive] glad we did.”
As someone who sells software, there’s no greater compliment than a boomerang customer.
Evan always had someone to call at Pilot, and he felt like everyone he worked with at Pilot was helpful and responsive. During the acquisition process, his usual point of contact was out of office, and he was able to escalate the issue and have a member of the Pilot team join an important call with all of the parties involved the very next day.
Not only was the day-to-day and month-to-month stuff great, but when push came to shove, Pilot was on the money... It was a great experience.
After three years of operation, Tola was acquired by Square. As part of the acquisition process, Evan handed over the books generated by Pilot. As Evan said, “They had 135 people on our deal. The books stood up to real scrutiny.” As of Fall 2025, Tola has now been folded into Square.
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