About the role

About Pilot

Pilot provides bookkeeping, tax, and CFO services powered by software—helping companies operate with better financial visibility and confidence. We’re building the modern finance back office. We’re early in building our franchise channel and are looking for someone to help us figure it out from the ground up.

About the Role

We’re hiring a Growth Lead to build Pilot’s franchise channel from scratch. This is a high-ownership individual contributor role. You’ll operate like a mini–GM, staying deeply hands-on—running experiments, talking to operators and franchisors, launching campaigns, and driving pipeline yourself. This role is a strong fit for someone early in their career who wants to own a real business problem end-to-end.

What You’ll Do

Figure Out the Franchise Motion (0 → 1)

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)

Run Fast Growth Experiments

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

Be Close to Customers

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

Execute End-to-End

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

Own Pipeline

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

Build Early Partnerships

Identify and engage franchise ecosystems (POS systems, franchise consultants, associations)
Run co-marketing or co-selling experiments
Help Pilot become relevant within franchise networks

What We’re Looking For

You Might Be a Fit If:

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

Experience

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

How You Work

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)

Why This Role

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

What Success Looks Like (First 6–12 Months)

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

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 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 w

Skills & Tags

ai data product design marketing sales

Aplyr's read

Pilot is a tech-driven financial services firm, ideal for those passionate about simplifying financial processes for startups and small businesses.
Synthesized from recent postings & public sources

What's promising

•Pilot offers a tech-focused approach to traditional financial services, appealing to innovative professionals.
•The company supports startups, providing employees with exposure to dynamic and fast-paced environments.
•Pilot's recent hiring in strategic roles suggests growth and expansion opportunities.

What to watch

•Limited public information about Pilot's long-term financial stability.
•The niche focus on startups may limit broader industry experience.
•Potential high-pressure environment due to the fast-paced nature of client industries.

Why Pilot

•Pilot combines technology with expert teams to streamline financial management.
•The company's focus on startups differentiates it from traditional financial service providers.
•Pilot's strategic hiring indicates a commitment to expanding its market influence.

Aplyr’s read is generated by AI from public sources. Was it useful?

About Pilot

Pilot

pilot.com

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Pilot is a financial services company that specializes in bookkeeping, tax, and financial management for startups and small businesses. By leveraging technology and expert teams, Pilot aims to simplify financial processes, allowing entrepreneurs to focus on growing their businesses.