Pilot’s mission is to be the back office for every small business in America, and we’re hiring an engineering manager to help play a part in making this future a reality.

All of our teams have unique charters to collectively build the software, services and systems that enable Pilot to deliver a high-quality experience, profitably, at scale. We are building the modern financial back office for every SMB in America: giving every SMB the superpowers of a full finance team at a fraction of the cost. These superpowers include having a deep understanding of the financial health of the business, the machinery to constantly improve it, and the predictive abilities to thoughtfully plan for the future. We do this at a fraction of the cost a large company would pay for this, by delivering these capabilities through powerful software.

We’re looking for caring, empathetic engineering managers with a technical background that are excited to build and ship software iteratively. We value being close to our customers, iterating quickly, and learning from what we ship. Our teams operate on high trust, and we prioritize ownership over the outcomes you’re responsible for: building great products that move the needle for our customers.

From a technical perspective, Pilot’s backend is written in fully typed Python 3.11, and our frontend is JavaScript, TypeScript, and Vue.js. We use Terraform to manage our production infrastructure, and deploy Docker containers to ECS. AWS CodeDeploy powers our deployments and we rely on Honeycomb for our monitoring and Postgres as our database.

Key Responsibilities

Lead a team of talented engineers who like to ship code and tackle hard engineering problems.
Mentor and guide the professional and technical development of your team members. Help develop their careers, and assign them to projects tailored to their skill levels, personalities, work styles, and professional goals.
Create a team environment that values collaboration, inclusion, and respect.
Provide continuous feedback, address underperformance, and recognize the individual strengths and contributions of your team members.
Create plans for prioritizing technical and resourcing challenges within the team, within the context of the larger Engineering organization.
Instill a spirit of continuous improvement in the team’s code, architecture, and processes.
Grow the team thoughtfully by understanding business needs, addressing team skill gaps, and prioritizing a diverse top of funnel.
Work with your engineers and stakeholders to maintain a prioritized backlog and create short term and long term goals.
Help your team build relationships across Engineering, Operations, and any other stakeholders who are relevant to the team’s strategy.
Work across teams to shape development at Pilot (e.g. defining best practices, choosing technologies, evolving our tech stack).
Think medium- to long-term. We are building for Pilot’s future accelerated growth and need someone with strong foundations who will set us up to scale

About You

In order to successfully fulfill the responsibilities outlined above, we have a small set of requirements. As our ideal candidate, you will have at least two years of experience in an official managerial role, and you can demonstrate experience with most the following:

Managing engineers’ performance: This could include managing out, performance corrections, giving continuous feedback, and investing in strong performers.
Growing teams: You can identify the need for headcount, define hiring criteria, and act as an owner throughout the entire recruiting lifecycle.
Technical execution and dependency management: Your teams have shipped complex features with dependencies or stakeholders from outside the team, and you’ve played a significant role in their execution.
Team dynamics: You’ve diagnosed a number of issues affecting morale or execution and found various solutions.
Fostering inclusion within a diverse team: We are a diverse team representing a variety of identities and experiences. Our managers must show an ability to understand and support the needs of marginalized individuals.
Relationship building: Whether it’s with your engineers, peers, customers, or vendors, you invest in relationships that benefit your team.
Technical design and strategy: While we expect little to no code output from our Engineering Managers, we look for folks with strong technical backgrounds who can hold their own in technical design discussions and represent the details of their team’s technology to others.

Note: while we do look to hire Engineering Managers with prior engineering management experience, even if you don’t exactly fit all of the requirements above, we’re always interested in talking to great managers, so get in touch!

About Pilot

Pilot launched in 2017 to bring the back office into the modern era. Pilot provides small businesses with dedicated finance experts - which Pilot hires as full-time, U.S.-based employees - who learn the ins-and-outs of their business. Pilot integrates directly with the billing, banking, expense, and payroll systems customers already use. With a special blend of custom software and expert bookkeepers, Pilot delivers accurate, consistent bookkeeping and financial management and tax services that give entrepreneurs the freedom to focus on their business.

Pilot has over 1,000 customers and has raised over $170 million in financing from Sequoia, Index Ventures, Stripe, Bezos Expeditions, and Whale Rock. Our investors also include a long list of world-class entrepreneurs, including Patrick and John Collison, Drew Houston, and Diane Greene. Our most recent funding round doubled our valuation to $1.2 billion – Meet Fintech’s Newest Unicorn.

Why Pilot?

We invest in our employees’ development and happiness because our employees are the keys to our success and ensuring happy customers
The opportunity to join a seasoned founding team that has led companies through two prior successful startups and acquisitions (by Oracle and Dropbox).
Flexible vacation/time-off policy
All federal holidays are observed
Competitive benefits package including wellness benefits such as Modern Health, Headscape, One Medical, Aaptiv and Rightway
Parental leave for birthing or non-birthing parents – 100% pay for 12 weeks
401(k) plan

The base pay range target for the role seniority described in this job description is $145,00 - $247,000 in most remote locations, and between $182,000 - $247,000 in San Francisco, CA and New York City, NY. Final offer amounts depend on multiple factors such as candidate experience and expertise, geographic location, total compensation, and market data. In addition to cash pay, full-time regular positions are eligible for equity, 401(k), health benefits, and other benefits; some of these benefits may be available for part-time or temporary positions.

Pilot commits to provide a work environment free of discrimination and harassment, as well as equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or Veteran status. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements. You may view all of Pilot’s recruiting notices here, including our EEO policy, recruitment agency policy, recruitment scam notice, and important E-Verify information.

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