Senior Engineering Manager, Customer Experience

  • Location
    • San Francisco
  • Date Posted
  • May. 24, 2021
  • Function
  • Software Engineering
  • Sector
  • Business Applications

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 Pilot’s Customer Experience organization and shepherd the team through its imminent expansion into multiple customer-impacting teams. This role comes with additional headcount for engineers in the short term, and we expect to continue to grow and spin out additional teams in the back half of the year.

The Customer Experience org’s mission is to accelerate Pilot’s growth by building features in Pilot that attract prospects and delight our existing customers. They are responsible for all of the major end-customer touchpoints, our financial insights products, sales and marketing enablement (i.e. a traditional Growth team), as well as our tax product offering. Simply put this is a highly strategic role that interfaces with large portions of the business, from Sales and Marketing to Customer Success and GMs of key business units.

The responsibilities of this role include:

  • Lead a team of talented engineers who like to ship code and tackle hard engineering problems.
  • Grow the current team into a set of distinct product teams in the near term, and plan for their continued growth throughout the rest of the year. Build a strong leadership bench that will include hiring additional Engineering Managers in the medium-term.
  • 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. Develop a vision for your organization’s growth over the next 8-12 months and iterate on team’s overall yearly strategy.
  • 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, Product Manager, and cross-functional stakeholders to maintain a prioritized backlog and create short term and long term goals.
  • Help your team build relationships across Sales, Marketing, Customer Success, and any other stakeholders who are relevant to the team’s strategy.
  • Participate in reviews of technical or product specs to provide your perspective on the features we want to build.
  • 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 set of requirements. As our ideal candidate, you will have at least three 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.
  • Managing managers and/or senior leads: We expect to grow this org quickly, so our ideal candidate already has experience hiring managers and/or transitioning individual contributors to management. Alternatively, you’ve managed senior technical leads and can demonstrate thoughtfulness around succession planning and delegation.
  • 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 decision making: 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.
  • Setting long term strategy: You can communicate a strong vision that helps your team understand how they contribute to and further the business. You can demonstrate long-term strategic thinking and build or iterate on an organization’s long term strategy (in conjunction with your Product Management counterpart(s)).

About us

Pilot is a high growth software startup that automates much of the heavy lifting in financial services (e.g., bookkeeping, tax, CFO services, etc.) for SMBs. Since launching in 2017, Pilot has built highly advanced engineering to automate these financial services.

Our EPD (Engineering, Product, and Design) org began the year divided into three cross-functional teams, each with their own missions, charters, and internal stakeholders. We are expecting to grow both the business and our headcount significantly this year, aiming for roughly six teams by mid-2021. 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. Many of our projects start and end with detailed user research and input from Product Design.

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.

Pilot has raised over $120M in Series A, Series B and Series C financing from Sequoia, Index Ventures & Stripe. The company’s investors include a long-list of world-class entrepreneurs, including Patrick and John Collison, Drew Houston and Diane Greene.

Pilot’s seasoned founding team has led companies through two prior successful startups and acquisitions (by Oracle and Dropbox). Pilot is headquartered in San Francisco and has a second office in Nashville. The company is scaling rapidly and has 150 employees.

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.