Job Description

The Role

At Pilot, we believe access to the right financial resources and expertise can change the trajectory of a business. Our combination of AI and human experts gives startups and SMBs a level of insight that used to be reserved for companies with fulltime finance teamsan experience that feels boutique, but is actually affordable and scalable. In doing so, we help founders and operators find their flow by taking the burden of the financial back office off their plate.

Were looking for a Finance Content & Storytelling Lead who can explain financial concepts clearly, creatively, and crediblyespecially through short-form video , live discussions and educational content .

You do not need to come from a traditional marketing background. You might be:

• A bookkeeper or accountant who loves teaching financial concepts.
• A creator (YouTube, TikTok, Shorts, Reels, LinkedIn) who enjoys breaking down complicated topics.
• A writer, educator, or operator who wants to translate your realworld knowledge into approachable content.

If you can make complex ideas simple and engaging, this role is for you.

This is a hybrid role based in SanFrancisco or Nashville , with inoffice days on Monday, Tuesday, and Thursday .

Who Youll Create For

1. Startup founders and small business owners who feel overwhelmed by their finances and need clarity.
2. Bookkeeping firms who want better tools, better workflows, and a modernized practice by partnering with Pilot.

What Youll Do

Make Finance Clear & Relatable

• Explain how Pilots AI + human experts take the weight of the financial back office off founders shoulders.
• Break down bookkeeping, cash flow, margins, and growth concepts in ways that feel human, useful, and nonintimidating.
• Use content to move founders from my books are a mess and I dont want to think about them to Pilot has my back office handled so I can focus on growing.
• Design parallel content journeys for bookkeeping firms and ecosystem partners, from why would I work with Pilot? to this makes me more effective at serving my community/clients.

HandsOn Content Creation

• Script and record socialfirst short videos that simplify financial topics and showcase real stories.
• Build outlines for panels and live discussions that make experts shine and produce reusable content.
• Write explainers, guides, and playbooks on SMB finance topics based on realworld problems customers face.
• Create simple storyboards and content series that help founders and bookkeeping firms learn in repeatable, bingeable formats.

Use AI to Work Smarter, Not Harder

• Turn Zoom calls with experts, customer stories, and partner insights into scripts, outlines, and drafts.
• Repurpose a single conversation or panel into multiple assets (clips, explainers, templates, partner resources).
• Use AI tools to brainstorm, structure ideas, and iterate quicklywhile keeping your strong human voice.

Learn Directly From Experts

• Interview Pilots bookkeepers, controllers, CFOs, and customerfacing teams.
• Pull insights from partners like CDFIs, SBDCs, and trade associations about what local businesses struggle with.
• Turn real conversations into content that feels grounded, helpful, and authentic.

Experiment & Improve

• Test hooks, formats, visuals, and topics to see what resonates with founders and firms.
• Track simple performance metrics like engagement, watch time, and contentinfluenced leads.
• Adjust your content strategy based on whats actually helping people.

Why Youll Love Working with Pilots Marketing Team

You wont be doing this alone in a corner. Youll be joining a small but mighty marketing team that cares about both craft and impact.

• Senior, collaborative teammates Youll work with experienced demand gen, social media, product marketing, partner/local programs, and ops folks who know their craft and respect yours. You bring the stories and creative formats; they bring distribution, data, and GTM alignment.
• Tight partnership with leadership Youll be close to decisions and able to see your work turn into real programs quickly, not stuck in layers of approvals.
• Room to experiment The team values testing and learning. Youll have space to try new formats, angles, and ideas as long as were learning and getting sharper each time.
• Access to rich raw material 3,000+ customers, deep finance expertise inhouse, and a growing partner ecosystem mean youll never be short on stories, data points, or realworld examples.
• Mission that actually matters Youll help make highquality financial operations accessible to the kinds of businesses that usually get left behind through content that genuinely helps them.

About You

• You have a strong portfolio of work that shows you can explain complex topics in a clear, engaging way.
• You might be a former bookkeeper/accountant/operator, a social media creator, a writer/educator, or something in between.
• Youre excited by the idea of living in the bookkeeping / SMB finance / small business ecosystem and turning that world into content that founders, bookkeeping firms, and partner organizations actually want to watch and read.
• Youre comfortable being both the thinker and the doer. You like owning the idea and making the thing.
• Youre scrappy: you enjoy figuring out how to make a lot with a little, using AI, systems, and creativity more than large budgets.
• Youre curious about AI tools and already use them (or want to use them) to move faster and be more creative.
• You care that your work helps real people: founders, small business owners, bookkeeping firms, and the ecosystems that support them to get to better outcomes.

About Pilot

Pilot launched in 2017 to bring the back office into the modern era. Pilot provides small businesses with dedicated finance experts Pilot hires them as fulltime 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 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 worldclass entrepreneurs, including Patrick and John Collison, Drew Houston, and Diane Greene. Our most recent funding round doubled our valuation to $1.2billion Meet Fintechs 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/timeoff policy.
• All federal holidays are observed.
• Competitive benefits package including wellness benefits such as Spring Health, Headscape, One Medical, Aaptiv, and Rightway.
• Parental leave for birthing or nonbirthing 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 $215,000 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, fulltime regular positions are eligible for equity, 401(k), health benefits, and other benefits; some of these benefits may be available for parttime 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 Pilots recruiting notices here, including our EEO policy, recruitment agency policy, recruitment scam notice, and important EVerify information. You may view our job candidate privacy policy here.

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