Head of Strategic Marketing

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The Role

Most marketing leaders inherit a playbook. This one gets to write and scale it.

The motion is enterprise B2B—longer cycles, multiple stakeholders, relationships that close deals. Pilot has that motion working. Your job is to point it at 3 distinct segments and build everything behind it. The segments are distinct:

• Strategic accounts are growing businesses with significant annual revenue or institutional funding and real operational complexity—and have been Pilot's bread and butter for years. This segment doesn't need to be proven. It needs more behind it.
• Franchisors are corporate buyers whose vendor decisions cascade across entire franchise systems—win one, and you've won dozens of locations.
• Franchisors are corporate buyers whose vendor decisions cascade across entire franchise systems—win one, and you've won dozens of locations.
• And Mid-market accounting firms adopting Pilot as the platform they run their clients' books on, at scale.

We’re building a partner-led growth model that scales through relationships rather than ad spend. This role is about extending that model across new segments in a way that drives consistent, measurable pipeline.

This role is ideal for a senior marketing leader who has built and scaled demand programs in complex B2B environments and is ready to take on broader ownership. You’re equal parts strategist and experimenter—excited to unlock new growth channels, test bold ideas, and deepen a partner ecosystem as a meaningful driver of acquisition.

You'll report to the VP of Marketing and manage two senior direct reports: a Senior Demand Generation Manager and a Partner Marketing and Events Lead. You'll also work with a shared team of senior specialists across lifecycle marketing, marketing operations, product marketing, and content—giving you the support to build full-funnel programs without building a large team from scratch.

This is a hybrid role requiring presence in our San Francisco office on Mondays, Tuesdays, and Thursdays.

What You’ll Own

• Segment strategy. Each segment requires a distinct motion—but all three share the same enterprise foundation. You’ll define how we approach each and make that strategy actionable.
• Pipeline. You’re accountable for what these segments produce. In close partnership with sales, you’ll align on account prioritization and build programs that move the right prospects from first impression to signed contract.
• Partner pipeline. You’ll build on and scale our partner-led motion—working with our Partner Marketing and Events Lead to turn relationships into a consistent source of pipeline through referral programs, co-marketing, and field engagement.
• Messaging. You’ll shape how Pilot speaks to each of these audiences—externally and in the materials our sales team uses every day.

What Success Looks Like in Year 1

• A clear, defensible go-to-market strategy across all three segments
• Repeatable demand and partner programs in market
• Growing, measurable pipeline contribution
• A team aligned around a clear roadmap and direction for year 2

About You

You’ve marketed to complex B2B buyers before—multi-stakeholder, longer sales cycles, relationships that matter. You understand the difference between selling to a partner and selling through one, and you’re comfortable building programs that support both. You’re ready to take on broader ownership across segments, pipeline, and strategy—and operate through a team to make it happen.

More specifically:

• 10+ years of B2B marketing experience, including time in enterprise or multi-stakeholder sales environments
• Experience managing and developing direct reports
• Strong foundation in demand generation and/or account-based marketing (ABM), including pipeline ownership and conversion metrics
• Experience partnering closely with sales leadership on account prioritization and pipeline goals
• Exposure to partner or channel marketing (direct ownership or close collaboration)
• Writes and communicates clearly

Nice to have: experience marketing to franchisors or accounting firms, or familiarity with bookkeeping, tax, or CFO services.

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 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 $159,000 - $250,000 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.