- Understand how franchise systems buy (corporate vs franchisee vs both)
- Identify high-potential segments (e.g., QSR, fitness, home services, multi-unit operators)
- Test different entry points (top-down via franchisor vs bottom-up via operators)
- Launch scrappy tests across channels (events, outbound support, partnerships, content, paid)
- Try different GTM motions (corporate deals, multi-location bundles, pilot programs)
- Use results to determine what scales
- Talk directly to franchise owners, operators, and corporate teams
- Understand operational pain points (unit economics, reporting, cash flow, multi-entity complexity)
- Translate insights into messaging and acquisition strategies
- Build landing pages, write emails, run outreach, and launch campaigns yourself
- Stand up webinars or events tailored to franchise operators
- Move quickly with minimal process or support
- Be accountable for generating qualified opportunities and contributing to revenue
- Partner closely with Sales to refine positioning and improve conversion
- Focus on what drives deals across different buyer types
- Identify and engage franchise ecosystems (POS systems, franchise consultants, associations)
- Run co-marketing or co-selling experiments
- Help Pilot become relevant within franchise networks
- You’re early in your career but have strong business judgment
- You’ve taken ownership of something ambiguous before
- You’re excited to do the work yourself—not just design strategy
- You’re comfortable navigating messy, multi-stakeholder environments
- 2–5 years of experience in consulting, banking, startups, GTM roles, or similar
- MBA or equivalent experience is a plus, not required
- Exposure to SMBs, multi-location businesses, or operations-heavy industries is helpful
- High ownership: you take responsibility for outcomes, not just tasks
- Scrappy: you find ways to get things done with limited resources
- Analytical: you use data to guide decisions and prioritize
- Clear communicator: you can tailor messaging to different audiences (operators vs HQ)
- You’ll own a new growth channel with real revenue impact
- You’ll work across Sales, Partnerships, and Product
- You’ll gain exposure to complex GTM problems (multi-entity buyers, channel strategy)
- You’ll help define how Pilot wins in a large, underpenetrated market
- Clear signal on whether top-down (franchisor) or bottom-up (operator) motion works best
- 2–3 channels consistently generating qualified pipeline
- Early wins with franchise groups or multi-unit operators
- Initial repeatable plays for acquiring and expanding within franchise systems
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 3,000 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 additional wellness benefits
- Parental leave for birthing or non-birthing parents – 100% pay for 12 weeks
- 401(k) plan
The base pay range target for the role seniority described in this job description is $133,000 - $179,000 in San Francisco, CA. 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, information about requesting a reasonable accommodation in the job application process, recruitment agency policy, recruitment scam notice, and important E-Verify information. You may view our job candidate privacy policy here.
What We Do
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.
Why Work With Us
Pilot is truly a diverse company. We embrace people from all backgrounds including those who were formerly incarcerated. In addition, with our high growth environment we love to promote people within and offer them great career opportunities.
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