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

Set strategy and goals for digital acquisition across channels like Google and Bing Ads, LinkedIn, Meta, YouTube, and OTT.

Drive creative testing, landing page optimization, and media mix planning in collaboration with senior marketers and agency partners.

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.

Leverage AI and automation to generate personalized campaigns at scale while maintaining message relevance and quality.

Lifecycle & Funnel Acceleration

Guide full-funnel lifecycle strategy to increase conversion across all funnel stages.

Oversee nurture programs, retargeting, and behavior-triggered sequences to engage and advance prospects.

Own lead scoring frameworks, funnel diagnostics, and handoff processes in collaboration with Sales and RevOps.

Drive measurable impact on lead-to-opportunity conversion and deal velocity.

Marketing Operations & Tech Stack

Oversee marketing operations and reporting infrastructure, ensuring accurate attribution and funnel visibility.

Manage and optimize tools including Salesforce, Marketo, Bizible, GA4, Unify, Influ2, and others.

Partner with RevOps and Data teams to ensure clean data flow, align on reporting infrastructure, funnel metrics, and automation systems.

Team & Agency Leadership

Lead a small but mighty team of senior marketers—providing strategic direction, coaching, and prioritization.

Oversee relationships with agencies and contractors to augment execution across paid, ops, and outbound programs.

Establish clear KPIs, workflows, and feedback loops across internal and external partners.

Cross-Functional Collaboration

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.

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.

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?

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.

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