Pilot: A Smarter Back Office for Every Startup and SMB

Jan 26 · 3 min read
Pilot co-founders: Jeff Arnold, Waseem Daher, & Jessica McKellar

By Pat Grady and Michelle Bailhe on behalf of Team Sequoia

We first heard of Pilot’s founders, Waseem, Jeff and Jessica, one decade and two companies ago, when they were fresh out of MIT and working on their first company, Ksplice (which they sold to Oracle). We intersected with them more directly in 2016 when our partner Bryan was deployed to help persuade them to stay at Dropbox, which had joined forces with their second company, Zulip. Unfortunately, we failed in our mission, and Waseem, Jeff and Jessica left to start Pilot. Fortunately, we stayed in touch.

Fast forward to 2020. As we spent more time with the founders, we came to realize just how exceptional they truly are. In CEO Waseem’s words, “at MIT, we weren’t just computer science people, we were computer club people — so, the nerdiest of the nerds.” CTO Jessica is a world-renowned open-source developer, and COO Jeff is an elite computer scientist even by elite standards. But it was not just their technical prowess that caught our attention — it was their commitment to doing the right thing for the long term. Even pre-COVID, the team had not set out to maximize growth, but to maximize customer success. And thus, when the pandemic hit and the rest of the industry went reeling, Pilot emerged as the clear leader in tech-enabled bookkeeping. We fell in love with the team, and we fell in love with their dream of making the back office painless for every small and mid-sized business.

Pilot offers bookkeeping, tax and CFO services, but what it really solves is the perennial problems of too many questions and too little time. Bookkeeping is a must-have for every company, but while large companies have teams of accountants, small companies do not. Thus, most entrepreneurs face a choice: spend nights and weekends laboring over QuickBooks, or just outsource it. Neither of these options provides the delightful, tech-first approach we’ve all come to expect from our vendors. Pilot’s founders experienced this firsthand at their prior startups, and built Pilot to be the back-office solution they wished they’d had.

Pilot earned its customers’ trust by combining intelligent software with world-class accountants to deliver quality books at an affordable price. The engineering team is automating away all of the mundane work that’s not worthy of an accountant’s (or entrepreneur’s) valuable time, creating a better customer experience, and freeing up precious time and energy to create moments of delight. For example: Pilot is using the collective intelligence of 1,000+ customers to deliver insights and advice that traditional bookkeeping has never offered, such as: “You are paying 50% more for web hosting than peers of your size and industry, here’s how to reduce your bill using reserved instances” and “Based on your payroll and spend data your small business is eligible for a $60,000 government credit and we can help you claim it.” These are just two examples of the “wow” features Pilot is producing for its customers. Pilot has taken bookkeeping from tedious to painless, and is now taking it from painless to delightful.

The full potential of AI to alleviate rote cognitive labor won’t be realized overnight, but the transition is inevitable — and we believe Waseem, Jeff, Jessica and their team have the technical talent, operational rigor, customer-obsession and patience to build a legendary company. We are honored to partner with them on their journey to provide the back office they always wanted — and the one every startup and SMB deserves.

Sequoia Capital Publication

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