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 Vertical Strategy Director at Pilot. You will report to the VP & GM, Strategic Verticals. Your role will focus on identifying how we expand into new markets. 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

  • Help identify new markets, conduct initial research and help align resources across Pilot. Work with Sales, Marketing, and Partnerships to determine where and how we should expand. This person will help lead new market growth exploration, acting as a cross-functional leader to ideate market entry, score potential returns and provide recommendations to leadership.  
  • Market sizing and analysis: thoughtfully identify and aggressively execute a plan to grow in the verticals we think are most promising
  • Conduct primary and secondary research to identify market opportunities and develop both tactical and strategic solutions
  • Analyze internal business practices and how they impact new vertical growth, providing executive-level recommendations on how we can improve & optimize. In this role, this person will work closely with department heads and executives to understand our current operations, identify inefficiencies, model proposed outcomes, and make executive recommendations. 
  • Prepare and deliver persuasive, data-driven arguments and presentations to senior management to allow for informed strategic decision-making
 

About You

  • 8 to 12 years of experience in management consulting, investment banking or corporate strategy. 
  • Undergraduate degree required, preferably in a business or quantitative field. MBA is a plus. 
  • Strong analytical, strategic thinking, and problem-solving skills with the ability to define complex business problems, synthesize data, and provide and execute tactical and strategic solutions
  • Ability to work in a fast-paced environment, both independently and as part of a team, and under strict and changing deadlines
  • Self-starter with a strong sense of ownership, accountability, and work ethic
  • Strong project management, organizational, communication, and analytical skills
  • A track record of success and a demonstrated ability to exercise good judgment and discretion
  • Strong communication skills with the ability to distill complex issues into structured frameworks and concrete action plans

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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