Finance Content & Storytelling Lead

Pilot.com • Nashville, TN

7d • $127,000 - $172,000 • Hybrid

About The Position

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 full-time finance teams—an 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. We’re looking for a Finance Content & Storytelling Lead who can explain financial concepts clearly, creatively, and credibly—especially 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 real-world 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 San Francisco or Nashville, with in-office days on Monday, Tuesday, and Thursday

Requirements

• You have a strong portfolio of work that shows you can explain complex topics in a clear, engaging way.
• 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.

Nice To Haves

• You might be a former bookkeeper/accountant/operator, a social media creator, a writer/educator, or something in between.

Responsibilities

• 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.

Benefits

• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed
• Number of Employees: 51-100 employees