• Explain how Pilot’s 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 non-intimidating.
• Use content to move founders from “my books are a mess and I don’t 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.”

• Script and record social-first 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 real-world problems customers face.
• Create simple storyboards and content series that help founders and bookkeeping firms learn in repeatable, bingeable formats.

• 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 quickly—while keeping your strong human voice.

• Interview Pilot’s bookkeepers, controllers, CFOs, and customer-facing 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.

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

• Senior, collaborative teammates – You’ll 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 – You’ll 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. You’ll have space to try new formats, angles, and ideas as long as we’re learning and getting sharper each time.
• Access to rich raw material – 3,000+ customers, deep finance expertise in-house, and a growing partner ecosystem mean you’ll never be short on stories, data points, or real-world examples.
• Mission that actually matters – You’ll help make high-quality financial operations accessible to the kinds of businesses that usually get left behind through content that genuinely helps them.

• 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. 
• You’re 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.
• You’re comfortable being both the thinker and the doer. You like owning the idea and making the thing.
• You’re scrappy: you enjoy figuring out how to make a lot with a little, using AI, systems, and creativity more than large budgets.
• You’re 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 - 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 wellness benefits such as Spring 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 $127,000 - $172,000 in Nashville, TN. 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.