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Entrepreneur Relations Lead

Pilot

Pilot

Remote
USD 52-77 / hour + Equity
Posted on Oct 8, 2025
Apply now

The Role

Pilot helps small businesses thrive by delivering world-class bookkeeping, tax, COO and CFO services. We combine expert finance professionals with powerful software to give business owners the support they need to focus on growth.

We’re looking for a scrappy, enterprising individual to be Pilot’s boots on the ground in a specific market. This is a street-team style growth role: as Pilot’s Entrepreneur Relations Lead you’ll connect directly with small business owners, build trust, and create referral momentum within your community. The ideal candidate is already part of the small business world—whether you run your own business today or have in the past, and knows how to speak the language of entrepreneurs. If you bring the hustle, street smarts, and community connections, you’ll be empowered to make a big impact.

Key Responsibilities

  • Go out into the community—on the phone, online, or in person—and connect authentically with SMB owners.
  • Explain Pilot’s value in simple, practical terms that resonate with entrepreneurs.
  • Build credibility and relationships that turn into referral opportunities.
  • Tap into niche communities (including language- or culture-specific groups) and extend Pilot’s reach to audiences we couldn’t access otherwise.
  • Act like a growth engine: identify creative ways to expand the referral pipeline and build awareness.
  • Track your outreach and results, and share insights back to the team so we can double down on what works.

About You

  • A natural hustler with entrepreneurial drive—ideally a current or former small business owner.
  • Street smarts and resourcefulness; you know how to read people and situations.
  • Strong communicator who’s credible with business owners and comfortable leading real, unscripted conversations.
  • Deep ties to local or niche communities, especially if you speak a foreign language and can reach audiences others can’t.
  • Self-starter who thrives without a playbook and gets energy from making things happen.

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 2,000 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?

  • The opportunity to join a seasoned founding team that has led companies through two prior successful startups and acquisitions (by Oracle and Dropbox).
  • Drive impact and change the trajectory of Pilot - we’re small enough that your work makes a big difference in Pilot’s success.
  • All federal holidays are observed
  • 401(k) plan

The base pay range target for the role seniority described in this job description is $52 - $77 per hour in most remote locations, and between $64 - $86 per hour in San Francisco, CA and New York City, NY. Final offer amounts depend on multiple factors such as candidate experience and expertise, geographic location, total compensation, and market data. In addition to cash pay, full-time regular positions are eligible for equity, 401(k), health benefits, and other benefits; some of these benefits may be available for part-time or temporary positions.

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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