Remote job description

The Role

Pilot's Customer Operations organization is responsible for delivering our suite of products (Bookkeeping, Controller Services, CFO, Tax, and Extended Services) to our customers in a way that maximizes customer satisfaction, net retention, and margin. As a Senior Manager, you will collaborate with our VP, Customer Operations to identify and implement programs and processes that will enable us to better deliver on those metrics and efficiently scale a high-performing operations team (think OKR planning, customer onboarding, L&D, and operational process improvement and implementation). You may also be tasked with high impact multi-quarter special projects. No day is the same and you will need to adeptly maneuver moving from collaborating with the VP, Customer Operations and cross-functional teams across Pilot (Operations, R&D, Sales, Customer Success, etc.) to getting your hands dirty with process and tool implementation.


  • Ideation: Be a thought partner with operational leaders by bringing bold ideas to the table ?" whether that is testing new processes or tools to improve the customer experience
  • Process Improvement: Identify the most significant operational gaps, inefficiencies, and risks by creating strong relationships with operational and cross-functional leaders and leading implementation of those solutions
  • Program/Project Management: Be comfortable owning programs and projects that will meaningfully improve the customer and employee experience by improving our operational processes
  • Analyze: Quantify everything you do. Utilize data-driven decision making to understand business trends, identify problems, and build solutions
  • Iterate: Find the best solutions through iteration. Identify operational weaknesses in the service delivery experience and build scalable processes. Be comfortable with getting your hands dirty and implementing solutions.
  • Stakeholder management: Create and develop collaborative relationships with key cross-functional partners (e.g., Customer Success, R&D, Sales, and Revenue Ops) to deliver the most meaningful impact
  • Thought partnership: Act as thought partner and trusted advisor to the VP, Customer Operations on topics ranging from operations strategy to culture building
  • People Management: If the need arises, being able to manage a small team


  • Minimum of eight years of professional work experience in consulting, investment banking, strategy, or operations. Accounting experience is a plus!
  • Ability to thrive in a fast-paced and ambiguous environment
  • Excellent organization, time management and prioritization skills; proven ability to balance multiple critical tasks and consistently delivering against hard deadlines
  • An analytical and data-driven decision making mentality
  • Experience with or strong excitement for a get-your-hands-dirty environment
  • Impeccable verbal and written communication skills
  • Obsessively obsessed with attention to detail and leaves no stone unturned
  • Adept cross-functional partner who thrives on creating a delightful customer experience with other functional partners
  • Solid people manager who has managed small teams

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

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.

Company name: Pilot
Remote job title: Senior Manager, Operations Strategy & Implementation
Job tags: Investment Banking, Data-driven Decision Making, Prioritization Skills

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