Pilot.com
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The Role 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:
Bookkeeper or accountant who loves teaching financial concepts.
Creator (YouTube, TikTok, Shorts, Reels, LinkedIn) who enjoys breaking down complicated topics.
Writer, educator, or operator who wants to translate real‑world knowledge into approachable content.
This is a hybrid role based in San Francisco or Nashville, with in‑office days on Monday, Tuesday, and Thursday.
Who You'll Create For
Startup founders and small business owners who feel overwhelmed by their finances and need clarity.
Bookkeeping firms who want better tools, better workflows, and a modernized practice by partnering with Pilot.
What You'll Do Make Finance Clear & Relatable
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.”
Hands‑On Content Creation
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.
Use AI to Work Smarter, Not Harder
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.
Learn Directly From Experts
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.
Experiment & Improve
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.
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.
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 might be a former bookkeeper/accountant/operator, a social media creator, a writer/educator, or something in between.
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.
About Pilot Pilot launched in 2017 to bring the back office into the modern era. Pilot provides small businesses with dedicated finance experts—who are full‑time, U.S.‑based employees—who 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—Meet Fintech’s Newest Unicorn.
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, Headspace, One Medical, Aaptiv and Rightway.
Parental leave for birthing or non‑birthing parents—100% pay for 12 weeks.
401(k) plan.
Compensation & Benefits The base pay range target for the role seniority described in this job description is $127,000 – $172,000 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.
EEO Statement 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, marital status, 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 policy here.
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Get AI-powered advice on this job and more exclusive features.
The Role 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:
Bookkeeper or accountant who loves teaching financial concepts.
Creator (YouTube, TikTok, Shorts, Reels, LinkedIn) who enjoys breaking down complicated topics.
Writer, educator, or operator who wants to translate real‑world knowledge into approachable content.
This is a hybrid role based in San Francisco or Nashville, with in‑office days on Monday, Tuesday, and Thursday.
Who You'll Create For
Startup founders and small business owners who feel overwhelmed by their finances and need clarity.
Bookkeeping firms who want better tools, better workflows, and a modernized practice by partnering with Pilot.
What You'll Do Make Finance Clear & Relatable
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.”
Hands‑On Content Creation
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.
Use AI to Work Smarter, Not Harder
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.
Learn Directly From Experts
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.
Experiment & Improve
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.
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.
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 might be a former bookkeeper/accountant/operator, a social media creator, a writer/educator, or something in between.
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.
About Pilot Pilot launched in 2017 to bring the back office into the modern era. Pilot provides small businesses with dedicated finance experts—who are full‑time, U.S.‑based employees—who 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—Meet Fintech’s Newest Unicorn.
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, Headspace, One Medical, Aaptiv and Rightway.
Parental leave for birthing or non‑birthing parents—100% pay for 12 weeks.
401(k) plan.
Compensation & Benefits The base pay range target for the role seniority described in this job description is $127,000 – $172,000 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.
EEO Statement 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, marital status, 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 policy here.
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