Content Marketing & Creative Lead

Pilot.com • Nashville, TN

7d • $127,000 - $200,000 • 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 Content Marketing & Creative Lead who can bring this story to life across modern marketing channels—especially 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.

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 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.

Responsibilities

• 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 with—or joining—Pilot.
• 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.

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