pilot customer case study woebot

From Spreadsheets to Series A Funding: How Pilot Supported Woebot During Fundraising

with Alison Darcy, CEO & Founder

Woebot Labs created a novel chatbot to help those with anxiety and depression.


CEO and founder Alison Darcy had a lot on her plate. Between raising a round and building out her team, there wasn’t any time left to take care of bookkeeping.


Pilot was able to take bookkeeping off her plate, and was able to deliver key reports that investors wanted to see.


Woebot Labs got the hands-on support they wanted with the reports they needed to fuel their growth.

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The Woebot Labs Story

Woebot Labs is on a mission to make the best psychological tools and make them radically accessible for everyone. They have created a chatbot that can provide emotional assistance while also teaching core concepts based on cognitive behavioral therapy. While they are focused on helping those with anxiety and depression, they do not have time to be worried about bookkeeping and back-office tools.

Alison Darcy, CEO, and founder of Woebot Labs spoke to us about the journey of scaling her startup and the importance of having clear visibility into the numbers, even when you are not a finance expert. She told us, “I’d been in the academic world for a really long time, and bookkeeping is just not something that has ever been part of my role.” Given this, handling the bookkeeping was not something that would be practical, or even logical, to take on herself.

The Pilot team understood what I was going through and it was clear from the beginning they knew how early-stage startups operate. I did not have to spend hours explaining why I did or did not do something. The entire bookkeeping process - from start to upkeep - has been effortless.

Alison Darcy

CEO, Woebot Labs

Darcy reached out to Pilot while Woebot Labs was still in stealth mode. As the company was preparing for their launch, it was a hectic time for Darcy. “I was doing a press tour in New York, Washington, and San Francisco. I was overseeing all the hiring, and to top it all off, I was also fundraising. Mind you, I was doing this solo, so the last thing I wanted on my plate was bookkeeping,” she said.

Which is exactly where Pilot came in.


Woebot Labs’ growth was quickly accelerating, and Darcy needed to make sure that the books were in great shape for their investors. Fundraising is a make-or-break moment for startups, and she wanted to be sure they had built the right foundation that would let them successfully raise money and hire great people on the team.

In need of an expert that could scale with the company

Woebot Labs was preparing to scale, but still wanted to keep the team lean. Darcy explains, “We needed some serious bookkeeping. We didn’t want to find, hire, and manage an in-house finance person, but we needed to get our books in order.” This meant that it was time to pursue external solutions that met their needs—that also specialized in tech startups—which is how they came across Pilot.

Freeing time for high-leverage activities.

As the CEO and founder, Darcy does not have extra time on her hands. And if she did, it certainly would be put towards high-leverage growth activities, not keeping the books in order.

Darcy shares, “It is not about having the time to do the bookkeeping myself. It’s about prioritizing the bigger tasks at hand and having the wherewithal to lean on the experts, like Pilot, to help with overseeing the areas that are not my specialty.”

For Darcy, her time and efforts were on the most critical things: raising money, building a great team, and growing the business. That can’t happen if you’re spending all your time on bookkeeping and back-office maintenance.

pilot customer case study woebot

Paying off earlier bookkeeping debt

Looking back, Darcy shares that during the early days, there was no business account set up, many of the operations were going through her personal account, and things were being managed in Google Sheets. Darcy quickly realized that the lack of bookkeeping would become hazardous to the health of the company. She states, “We started to have expenditures of a real company, and we started making bigger and more consistent purchases. It all got too cumbersome to manage on our own.”


Woebot Labs was setting up their books for the first time, and that meant they needed some extra support to get everything set up and running smoothly.

With Pilot, they got a dedicated bookkeeper who was able to learn the ins and outs of their business. Darcy explains, “There was just so much attention from the Pilot team to help us go through that transaction by transaction. It was a beneficial process that got our books on track.”

Pilot is changing how bookkeeping is done. It’s the bookkeeping service of the 21st century.

Alison Darcy

CEO, Woebot Labs

Industry knowledge and expertise

Darcy reflects on this expertise, saying, “The Pilot team understood what I was going through and it was clear from the beginning they knew how early-stage startups operate. I did not have to spend hours explaining why I did or did not do something. The entire bookkeeping process - from start to upkeep - has been effortless.”

Pilot specializes in bookkeeping for high-growth startups. We know intimately the kinds of challenges these companies face as they raise funding and hire at a rapid rate. This knowledge was essential to Woebot Labs as they chose their bookkeeping provider.

A great value

Cost and value were the top factors for Darcy. She says, “We are a startup. We need to be frugal in our spending. Working with Pilot, there has been an obvious ROI.” At Pilot, we know how important it is to spend money wisely as your business grows. High-quality bookkeeping is a smart investment — but it should not cost an arm and a leg.

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