Pilot.com · 1 month ago
Content Marketing & Creative Lead
San Francisco, CA
Full-time
Hybrid
Senior Level
$159K/yr - $250K/yrPilot is a company that provides financial resources and expertise to startups and SMBs through a combination of AI and human experts. They are seeking a Content Marketing & Creative Lead to develop and execute content strategies that engage startup founders and bookkeeping firms, showcasing the value of their services through various modern marketing channels.
AccountingArtificial Intelligence (AI)Bookkeeping and PayrollFinancial ServicesFinTechProfessional ServicesSoftware
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
Qualification
Required
Strong portfolio of work that shows the ability to explain complex topics in a clear, engaging way
Excitement about 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
Comfortable being both the thinker and the doer; likes owning the idea and making the thing
Scrappy; enjoys figuring out how to make a lot with a little, using AI, systems, and creativity more than large budgets
Curious about AI tools and already uses them to move faster and be more creative
Cares that work helps real people: founders, small business owners, bookkeeping firms, and the ecosystems that support them to get to better outcomes
Benefits
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
Company
Pilot.com
Pilot provides the most reliable accounting, CFO, and tax services for startups and small businesses.
Founded in 2016
201-500 employees
H1B Sponsorship
Pilot.com has a track record of offering H1B sponsorships. Please note that this does not
guarantee sponsorship for this specific role. Below presents additional info for your
reference. (Data Powered by US Department of Labor)
Distribution of Different Job Fields Receiving Sponsorship
Represents job field similar to this job
Trends of Total Sponsorships
2025 (61)
2024 (18)
2023 (21)
2022 (31)
2021 (11)
2020 (1)
Funding
Current Stage
Growth StageTotal Funding
$172.1MKey Investors
Akkadian VenturesIndex Ventures
2022-01-01Series Unknown
2021-06-01Secondary Market
2021-01-26Series C· $110.5M
Leadership Team
Jessica McKellar
Founder and CEO
Recent News
2025-12-18
SV Angel
2025-12-01
Company data provided by crunchbase