What we’re building

Every company needs to keep track of its finances, and most hire a bookkeeping firm to help do so. But there's no Stripe, Gusto, or Google Apps of this world—no clear best-in-class firm that everyone uses because it delivers a service of unmatched quality and integrates with the tools and workflows to run your business as it grows. Pilot is building a first-of-its-kind, software-centric solution to tackle the financial back office (including bookkeeping, tax, CFO, etc.) so that founders and business owners don't have to.
 
Our approach is to use software to automate as much of the heavy lifting as possible and giving those software superpowers to a team of finance experts. This means that our customers, business owners, can focus on the reasons they started their businesses in the first place, instead of worrying about whether their bookkeeping is being done well.
 

The role

We are looking for an experienced engineering manager to lead our Infrastructure team. This team’s mission is to empower the Engineering, Product, and Design (EPD) teams with the tools they need to confidently ship, test, measure and learn from the products they build
 
The Infrastructure team has the opportunity to build the foundations for Pilot’s growing product suite. The team’s portfolio of work spans security, reliability, product infrastructure, and performance. We prioritize projects that focus on security and reliability, as well as projects that have cross-organizational impact on engineering velocity. 
 
The responsibilities of this role include:
  • 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 Infrastructure team’s strategy.
  • Participate in reviews of technical or product specs to provide your perspective on the features we want to build. This team does not currently have a Product Manager (though we’d like to open up this role in the future!) so we currently rely heavily on the Engineering Manager and engineers themselves to play this role.
  • Work across teams to shape development at Pilot (e.g. defining best practices, choosing technologies, evolving our tech stack).
 

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 one year of experience in an official managerial role, and you can demonstrate experience with most of the following:
  • Managing engineers’ performance: This could include managing out, performance corrections, giving continuous feedback, identifying goals and stretch assignments, 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.
  • DevOps or Infrastructure technology: For this role, we are preferring managers with a technical or management background in the DevOps or Infrastructure space. The team is also responsible for infrastructure security, and while we expect to build security-specific domain expertise over the next year (and split product security into its own team down the road), past experience with product security is a bonus.

About us

Our 25-person Engineering org is divided into three separate teams, each with their own missions and charters. We work collaboratively: we pair with each other (often across teams), we work on projects in groups, and we meet with our customers to inform what we build.
 
Pilot’s backend is written in fully typed Python 3.8, 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 Postgres as our database. While we have a smattering of other services, we believe deeply in infrastructure simplicity and strive to maintain a simple, streamlined set of infrastructure components. 
 
Overall, Pilot is about 135 people split across our San Francisco and Nashville offices. Our Engineering team is located in San Francisco, and our SF office is located right next to the Montgomery Street BART stop — though of course right now we are all working from home. We are currently only considering managers who live in or will relocate to the San Francisco Bay Area post-COVID.
 
Our seasoned founding team has led companies through two prior successful startups and acquisitions (by Oracle and Dropbox), and our engineering managers have a breadth of experience at companies of varying sizes. We invest in managers via peer mentorship and forums that meet at least quarterly across all functions.
 
We offer competitive benefits, including medical, dental, and vision coverage, as well as a 401(k) program.
 
At Pilot, we are enthusiastically pursuing and hiring a diverse workforce. We do not make hiring or employment decisions on the basis of race, color, religion or religious belief, ethnic or national origin, nationality, sex, gender, gender-identity, sexual orientation, disability, age, military or veteran status, or any other basis protected by applicable local, state, or federal laws. However, we do encourage applicants of all backgrounds and identities to apply.
 
Pilot also welcomes the opportunity to consider qualified applicants with prior arrest or conviction records. Pilot’s demonstrated commitment to diversity extends to hiring talented individuals in spite of a prior criminal history in accordance with local, state, and/or federal laws, including San Francisco’s Fair Chance Ordinance.

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