101 - 250 employees
11 - 25 engineers
$100m+ funding
Series c

Every business in the world has to keep track of its bookkeeping, and it's a terrible, expensive, and slow process. Pilot solves that problem: by pairing a nimble engineering team with a small team of world-class experts, we do extremely high-quality bookkeeping work, so they can focus on growing their business. (Think: if Stripe or Gusto started a bookkeeping company)

Pilot.com photo 1 Pilot.com photo 2

Why join us?

  • This is the third startup for Pilot’s founding team, having sold the previous companies to Oracle (Ksplice) and Dropbox (Zulip). The engineering team has deep technical expertise, with ex-Dropbox, Stripe, and Apple engineers, including the original author and maintainer of the Twisted networking framework. This is a rare opportunity to get the experience of an early-stage startup without the dysfunction (either management or engineering) of your average early-stage startup.

  • We're solving a problem every single company has (and is legally required to solve): maintaining its financial records. We’re already serving hundreds of companies, generating seven figures of revenue, and following a very consistent exponential growth curve every single month. Product-market fit has been established, and it’s time to scale the business. (Which is why we raised a $40M Series B from Stripe and Index Ventures a few months ago.)

  • We ship fast and iterate in a tight loop—the team is small and lean, which means we can move really quickly (several deploys a day). At the same time, we also invest heavily in writing clean code, building good infrastructure, and paying down technical debt. On top of the ex-Dropbox, Stripe, and Apple team mentioned above, our CTO, Jessica McKellar, previously managed a 150-person engineering team at Dropbox and is widely recognized as an engineering leader throughout the industry.

Engineering at Pilot.com

Engineering team and processes

Our engineering priorities are drawn from two sources: direct product feedback from our bookkeeping team, and engineering projects that serve to constantly uplevel our technical infrastructure.

Our engineering planning cycle roughly looks like this: The first two weeks of a month, our bookkeeping team closes our customers' books. We track their time, and use the generated data to understand the highest priority areas in our product that we want to improve: our goal is to drive up the efficiency of the process by building software that allows our users to close our customer's books more effectively.

The data-driven output from the close informs our product roadmap and prioritization: since we are able to base our prioritization on up-to-date hard data, we know we are working on the highest impact projects we can be. Additionally, we integrate infrastructure projects into our roadmaps that will set us up for success down the line — to make sure we're not simply working on short-term improvements.

One out of every four weeks is a Polish Week — a week where engineers have the freedom to work on improvements they think are vital to our codebase and engineering quality: this might be paying down tech debt, re-architecting a system that has been painful to use, or fixing particularly annoying bugs for our users.

Technical Challenges
  • Our problem domain is complicated: financial record keeping is a complex topic, and we deal with customers who have sophisticated financial needs. Understanding and designing the best UI/UX for handling complex financial workflows is a core part of our everyday technical challenges.

  • As we work with our customers' existing financial stack, we already have challenges with handling significant volumes of financial data. We are constantly designing and planning ways to continue to scale along with the growth of our customers.

  • We strive to maintain a clean and simple codebase, and are willing to invest time in building abstractions to simplify our engineers' lives. For example, we've fully embraced Python 3, static types, and asynchronous programming paradigms in order to increase our developer productivity and happiness. We consistently challenge ourselves to uplevel our infrastructure and developer experience.

Tech stack

Working at Pilot.com

Our team is small and tight knit: we each lunch together every day and celebrate success together.

We value diversity and inclusion: over half of our engineering team is comprised of women.

We don't feel forced to stay late, and we don't drink alcohol in the office.

Perks & benefits
  • Generous Vacation

    We have unlimited PTO, and we actually use it. Everyone, from the CEO down, has taken at least one week contiguous time off multiple times in a year.

  • Free Food

    We provide breakfast and lunch.

  • Flexible Hours

    Our core hours are 10am-6pm, but there is no expectation that you work exactly those hours. Some engineers prefer to come in early and leave early, while others arrive late and stay late. Some team members also work from home to avoid commuting every day of the week.

  • Health Insurance

    We provide full medical and dental coverage.

  • Work from Home

    We let engineers work from home when it makes sense, up to one or two days per week.

  • Company Retreats

    We celebrate revenue milestones: in the past (2018) we've gone to Hawaii, and more recently (2019) spent a few days as a company at a retreat in Santa Cruz.

  • Relocation

    We offer a relocation bonus for candidates moving to San Francisco.

Our Team by the Numbers

Interested in this company?
Skip straight to final-round interviews by applying through Triplebyte.