Content Marketing & Creative Lead

Content Marketing & Creative Lead

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 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.

We're looking for a Content Marketing & Creative Lead who can bring this story to life across modern marketing channelsespecially social-first short-form video, editorial content, and structured formats for live panels, roundtables, and thought-leadership moments.

Your work will engage two core audiences:

• Startup founders and SMB operators who should be using Pilot.
• Bookkeeping firms who should partner with or join Pilot.

This role is perfect for a content marketer, creative strategist, or editorial storyteller who thrives in a hands-on, maker-first environment and is excited to blend brand storytelling, thought leadership, and performance-centric content. This is a hybrid role based in San Francisco or Nashville, with on-site presence required on Mondays, Tuesdays, and Thursdays.

What You'll Do

Build & Evolve Pilot's Content Narrative

• Shape the overarching story for founders and SMBs about how Pilot's AI + human experts deliver elite financial operations at an accessible price.
• Craft positioning and messaging that helps bookkeeping firms understand the value of partnering withor joiningPilot.
• Develop narrative frameworks that ecosystem partners (CDFIs, SBDCs, trade associations) can confidently adopt when referring businesses to Pilot.

Drive Full-Funnel Content Strategy

• Build content that moves founders from "my books are overwhelming" to "Pilot has this handled so I can grow."
• 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."
• Build a roadmap across formats: short video, live event scripts, written explainers, templates, and partner assets.

Hands-On Content Creation Across Channels

• Concept and script social-first short-form video.
• Develop outlines for panels and roundtables to highlight subject-matter experts and generate repurposable content.
• Write long-form content such as guides, teardowns, and playbooks about margins, cash flow, and modern back-office operations.
• Produce simple visual storyboards and repeatable content series.

AI-First Content & Creative Ops (Scrappy by Design)

• Use AI for research synthesis, outlining, summarization, and first drafts.
• Turn signature content moments (live events, deep dives) into multi-asset content families.
• Build scrappy systems and workflows that enable high output with minimal resourcing.

Deeply Understand SMEs, Customers & Partners

• Extract insights from Pilot's internal finance experts, customers, and ecosystem partners.
• Translate interviews, calls, and raw data into structured narratives and market-facing content.

Measure, Learn & Optimize

• Define simple, clear KPIs for your work, such as: Engagement and conversion on founder-, firm-, and partner-focused assets. Content-influenced leads and opportunities from SMBs and bookkeeping firms. Partner with Demand Gen, Marketing Ops, RevOps, and Product Marketing to understand what's working and adjust your roadmap accordingly. Experiment with different hooks, lengths, visuals, and formats for each audience and double down on the ones that consistently build trust and drive action.

Why You'll Love Working with Pilot's Marketing Team

You won't be doing this alone in a corner. You'll be joining a small but mighty marketing team that cares about both craft and impact.

• 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.

About You

• 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 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 expertswhich Pilot hires as full-time, U.S.-based employeeswho 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 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 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.

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 - $200,000 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, 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, recruitment agency policy, recruitment scam notice, and important E-Verify information. You may view our job candidate privacy