The Role

Pilot aims to be the financial back office for every company. We believe the best way to do this is by expanding in a vertical-specific way because each vertical has different buyer behavior, go-to-market motions, product needs, and willingness to pay.
 
We’re looking for a Strategic Verticals Planning & Operations Director at Pilot. You will report to the VP & GM, Strategic Verticals. Your role will focus on measuring, tracking, and planning how we grow in new verticals. Because this is greenfield expansion, we need to establish best practices and processes. You will be key in identifying and honing those. You’ll have the opportunity to flex both strategic and operational muscles, and think short- and long-term every day. 
 

Key Responsibilities

At the highest level, the objective is simple: help Pilot grow revenue in new verticals, ensuring that the customer experience is world-class. Of course, “simple” does not mean “easy,” and to do that will require some of the items below:
  • Financial & Operations Planning: Drive monthly, quarterly, and annual financial & operational planning metrics for our strategic vertical expansion. This includes translating our revenue targets into effort metrics before and after sales. 
  • Operations: Discover and document existing processes with the goal of determining bottlenecks to provide effective operations. Be the internal champion for our new verticals, identifying and articulating process changes needed to better serve our clients
  • Business Partnering: Build strong relationships across functions within the company and maintain an open flow of communication, to build a deep knowledge of current events in the business.
  • Reporting and analysis: Develop a framework to establish various KPIs to drive continuous process and service improvement. Develop and implement management dashboards, reporting, and presentations to company leadership for Strategic Verticals. Drive visibility into business performance and resource planning decisions. Analyze trends in revenues, costs, margins, pricing, and profitability across the Strategic Verticals company’s businesses.
  • Execute: Make progress even in ambiguous environments; create structure and drive impact with limited guidance or precedence.
 

About You

  • 10+ years experience in sales operations, accounting or finance
  • Bachelors/Master's degree in finance, accounting or other quantitative disciplines 
  • Advanced Knowledge of Excel, SQL 
  • Demonstrated knowledge of financial analysis and financial modeling
  • Ability to work under pressure of multiple projects and deadlines
  • Ability to effectively prioritize workload and manage changes in direction of the company
  • Ability to develop, interpret and apply required policies and procedures
  • Ability to motivate and encourage a team
  • Critical thinking and problem-solving skills
  • Resource management skills
  • Ability to make independent and sound decisions
  • Financial and budget competencies
  • Excellent verbal and written communication

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
  • 100% coverage of employee only (individual) benefits
  • 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.

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