Head of Demand Generation and Growth

What You’ll Do

• Build and scale a partnerships-led growth strategy—identifying, nurturing, and optimizing relationships with key platforms, communities, influencers, and strategic partners.
• Develop and execute high-impact, creative growth plays that elevate brand awareness and drive net-new pipeline across the startup and SMB markets.
• Champion a culture of experimentation—rapidly generating hypotheses, testing unconventional approaches, and scaling what works.
• Collaborate closely with Sales and RevOps on ICP alignment, opportunity modeling, and pipeline targets.
• Apply AI, automation, and data tooling to move faster, personalize at scale, and amplify team output.
• Use analytics to measure program performance, uncover insights, and guide strategic pivots.

• Lead creative ideation—develop bold concepts, new experiments, standout messages, and differentiated media strategies.
• Set strategy and goals for digital acquisition across channels like Google and Bing Ads, LinkedIn, Meta, YouTube, and OTT.
• Monitor CAC efficiency and ROI, ensuring acquisition efforts are performance-driven and attributable.
• Build outbound programs grounded in deep buyer research and problem-based messaging—not just persona or industry assumptions.
• Use technographics, firmographics, and behavioral triggers to develop scalable hypotheses about customer pain points.
• Use AI and automation to deliver personalized campaigns at scale without sacrificing message quality.

• Maintain oversight of lifecycle, nurture, and funnel diagnostics—but prioritize experiments, outbound, and partner-led activation over heavy lifecycle ownership.
• Ensure clean processes for lead scoring, handoff, and conversion optimization in collaboration with Sales and RevOps.

• Oversee marketing operations and performance infrastructure to ensure strong attribution, reporting fidelity, and funnel visibility.
• Partner with RevOps and Data teams to ensure alignment on reporting frameworks, data hygiene, and marketing automation.

• Lead and mentor a high-performing team of senior marketers—providing direction, coaching, and strategic prioritization.
• Manage agency and contractor partnerships to expand creative, paid, and operational capabilities.
• Establish clear KPIs, experimentation frameworks, and feedback loops across internal and external partners.

• Partner with the broader marketing team to activate content, campaigns, and cohesive buyer journeys.
• Collaborate closely with Sales, Product Marketing, RevOps, CFO Services, and R&D to align on GTM priorities and share funnel insights.
• Continuously refine messaging, segmentation, and positioning based on cross-functional input and performance data.

About You

• 8–10+ years in B2B demand generation with 2+ years managing teams
• Proven track record of developing and executing successful marketing strategies that drive growth - scaling organizations from $25M > $50M > $100M ARR
• Deep understanding of startup ecosystems and the specific challenges of selling to small businesses, including bookkeepers/bookkeeping firms.
• Highly analytical and data-driven—comfortable using metrics to guide strategy, forecast performance, and optimize programs.
• Experienced in building, mentoring, and influencing senior marketers in a collaborative environment.
• Fluent in modern demand gen approaches including ABM, intent-based targeting, trigger-based messaging, personalization, and predictive analytics.
• Excellent communicator and cross-functional leader—you collaborate effectively with Sales, RevOps, Data,  and R&D.
• AI-forward mindset—you leverage automation to scale quality, reduce manual lift, and move fast.

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?

• 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 wellness benefits such as Modern Health, Headscape, One Medical, Aaptiv and Rightway
• 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 $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.