Pilot.com · 1 month ago
Finance Content & Storytelling Lead
San Francisco, CA
Full-time
Hybrid
Senior Level
$159K/yr - $215K/yrPilot is a company that provides startups and SMBs with financial resources and expertise through a combination of AI and human experts. They are seeking a Finance Content & Storytelling Lead to create engaging content that simplifies financial concepts and helps business owners understand their financial operations.
AccountingArtificial Intelligence (AI)Bookkeeping and PayrollFinancial ServicesFinTechProfessional ServicesSoftware
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
Qualification
Required
Strong portfolio of work that shows ability to explain complex topics in a clear, engaging way
Experience as a bookkeeper, accountant, operator, social media creator, writer, educator, or similar
Excitement about living in the bookkeeping / SMB finance / small business ecosystem
Comfortable being both the thinker and the doer
Scrappy: enjoys figuring out how to make a lot with a little using AI, systems, and creativity
Curiosity about AI tools and willingness to use them to move faster and be more creative
Cares that work helps real people: founders, small business owners, bookkeeping firms, and supporting ecosystems
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