Head of Demand Generation and Growth

Overview

The Role At Pilot, we're building something special in the fintech space—removing the headache from back-office financial operations for startups and SMBs. As we scale, we’re seeking a strategic and hands-on leader to build a scalable, AI-powered growth engine that fuels predictable, high-quality pipeline across self-serve and sales-led motions. This role is ideal for a senior marketing leader with a proven track record in scaling demand generation programs at fast-growing companies. You’re equal parts strategist, operator, and systems thinker—AI- and data-forward, with a sharp understanding of what it takes to drive sustainable growth in a competitive market. You’ll join at a pivotal moment, with strong marketing foundations in place, a highly capable team of senior marketers, and the opportunity to lead our next chapter of growth on the path to $100M in revenue. This is a hybrid position with the expectation to work in the San Francisco or our Nashville office on Monday s, Tuesday s, and Thursday s.

What You\'ll Do

Strategic Growth Leadership

• Develop and execute omni-channel strategies to increase brand awareness and attract new customers in the startup and small business sectors.
• Prioritize efficiency, experimentation, and repeatable pipeline creation across self-serve and sales-led motions.
• Align closely with Sales and RevOps on pipeline goals, ICP focus, and campaign strategy.
• Use AI, automation, and data-driven tooling to accelerate execution and scale personalization.
• Utilize analytics to measure the effectiveness of demand generation campaigns, identify trends, and make data-driven decisions, adjusting strategies as needed for optimal results.

Acquisition Strategy and Oversight

Lifecycle & Funnel Acceleration

Marketing Operations & Tech Stack

Team & Agency Leadership

Cross-Functional Collaboration

About You

$50M >

$100M ARR

Ready to build a modern demand engine with precision, velocity, and buyer-first strategy? Join us.

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 base pay range target for the role seniority described in this job description is $185k - $250k 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, recruitment agency policy, recruitment scam notice, and important E-Verify information. You may view our job candidate privacy policy here.

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