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Head of Product Marketing

Paid time off
Parental leave
This job offer is closed.
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The Role

Pilot provides finance, accounting, and tax prep services for startups and growing businesses. We run the financial back office for thousands of businesses of all sizes and stages, and we’re partners in helping our customers build enduring businesses. When our customers work with Pilot, they’re paired with a dedicated team of Pilot experts that focus on helping their business succeed. Pilot’s magic is that we take this amazing team (of US-based full-time Pilot employees), and equip them with software superpowers—think the “Iron Man” suit of accounting—developed by our internal R&D team.

Our customers buy Pilot because they trust that we understand them and will take good care of them—in short, they buy because of our brand and messaging. Which is why this role is so critical.

The Head of Product Marketing will own the overall messaging and positioning strategy and execution for Pilot—establishing us as the trusted back-office partner for business owners everywhere. The role will report directly to the CMO and will own product marketing for all of the services offered by Pilot.

Pilot has been covered recently in leading publications such as CNBC, CNBC Broadcast, TechCrunch, Fortune, Business Insider (1) , (2), and others.

Key Responsibilities

  • Ultimately, your job is to build and run a high-performing product marketing team, focusing largely on three key areas: (1) messaging, positioning, and category creation, (2) sales enablement, and (3) expanding into new offerings or new verticals. Simply put, you and your team will help us tell our story to our customers, making sure that we’re reaching them authentically and compellingly.
  • You’ll work closely and collaboratively with the rest of the marketing team, our sales team, and our EPD teams to drive growth and develop product marketing strategies with real measurable, quantifiable impact on Pilot’s business
  • You’ll help us tell our story and ultimately define our category: what is Pilot? Why should you trust us? What can we do for you that no one else can do for you? Tactically, this will look like messaging and positioning work, mapping the buyer’s journey, and helping refine personas—as well as the creation of marketing tools: e.g., demos, website content,  demand gen assets, videos, webinar content, etc.
  • You and your team will represent the voice of the customer, working closely with the sales team to develop sales collateral, case studies, presentations, customer success stories, and other sales tools that allow us to improve our win rate, and enhance the productivity of the sales team
  • As we launch new offerings, or launch into new verticals, you and your team will drive plans for those launches, communicating our value proposition and helping us win new business
  • Of course, none of this is a solo effort—you’ll need to build a strong product marketing team: one that’s data-driven and focuses deeply on analysis of customer pain points and the buyer’s journey. You’ll need to hire, guide, and mentor top product marketing talent, and foster a cohesive, high-performing team. 

About You

  • You’re a compelling storyteller with a strong strategic and analytical mindset, and you’re excited to own outcomes end-to-end, continually refining and delivering the company’s narrative.
  • You have 10+ years of relevant work experience in B2B SaaS product marketing
  • You’re a proven leader who has worked cross-functionally and been directly responsible for important business outcomes
  • You have a demonstrated ability to clearly communicate a unique value proposition through messaging frameworks, website experiences, etc.
  • You have a deep passion for engaging with customers and prospects
  • You’re analytical—you know that you can’t manage what you can’t measure. You prefer data to anecdata, but you also know when to thoughtfully lean on each.
  • You’re not afraid to roll up your sleeves and go deep when it’s needed to get to the right outcome
  • You’re an experienced people leader who has built, developed and retained high performing teams

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 1,000 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
Recruitment fraud is a sophisticated scam offering fake job opportunities. This type of fraud can occur through false websites, impostor LinkedIn profiles, fake job postings on job boards, phishing e-mails claiming to be from the company, etc. The fraudsters often request recipients to provide sensitive personal or financial information (SSN, bank account, etc.) and/or to make payments.  
Please note that employment offers and any requests for information will always be made by a Pilot employee with a email address.  If you are receiving an employment inquiry or employment offer from a non email address, please assume it is not genuine.  Pilot never asks job seekers to make any payment as part of the recruiting process. If you have any questions about the authenticity of the Pilot recruitment process or an offer that you have received, please contact us by email at [email protected].  If you have provided monies or other sensitive personal information and suspect you are the victim of fraud, please contact your local authorities or the Federal Trade Commission at 1-877-382-4357 or online at


Pilot does not accept agency resumes.  Please do not forward resumes to our jobs alias, employees, or any other company location.  Pilot is not responsible for any fees related to unsolicited resumes.


Pilot is an equal opportunity employer committed to providing employees with a work environment free of discrimination and harassment.  We base employment decisions on business needs, job requirements, and individual qualifications, without regard to race, color, religion, or belief; national, social, or ethical origin; age; physical, mental, or sensory disability; sexual orientation; gender identity and/or expression; martial, civil union, or domestic partnership status; past or present military service; HIV status; family medical history or genetic information; family or parental status including pregnancy; or any other status protected by the laws or regulations in the locations where we operate.  Pilot will not tolerate discrimination or harassment based on any of these characteristics. 

Pilot welcomes the opportunity to consider qualified applicants with prior arrest or conviction records.  Pilot’s demonstrated commitment to diversity extends to hiring talented individuals in spite of prior criminal history in accordance with local, state, and/or federal laws, including San Francisco’s Fair Chance Ordinance and the California and Tennessee ban-the-box laws. 

If you are a qualified individual with a disability and need a reasonable accommodation in the job application process, please reach out to [email protected].


Federal law requires Pilot to confirm the identity and employment eligibility of all persons hired to work in the United States, and Pilot participates in the E-Verify program for this purpose.  Pilot will provide the Social Security Administration (SSA) and, if necessary, the Department of Homeland Security (DHS), with information from each new employee’s Form I-9 to confirm work authorization.

Please read the attached notices, available in English and Spanish, for important information.

Questions & answers for this position
  • What is the type of contract for this position?
    The contract for this position is a Full-time contract
  • Is telecommuting possible for this position?
    No, telecommuting is not possible for this position
About Pilot
Pilot takes care of your bookkeeping from start to finish so you can focus 100% on making your business succeed.
Accounting, Financial Services
251-1000 employees

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