Founding Accountant — Tax & Product

Cherry (trycherry.ai) is building AI tax and accounting for founders. We handle the full stack: incorporation, bookkeeping, filings, franchise tax, Form 5472, sales-tax nexus, and reporting.

We're looking for an ambitious accountant who wants more than a conventional accounting career.

This is a chance to help build the system that makes tax and accounting work, not just operate within someone else's process. You'll work directly with our founders, early customers, product, and engineering team to turn real accounting judgment into software that helps every future customer.

What you'll do

• Help own the bookkeeping, reconciliations, closes, and compliance calendar for customers.
• - Work on filings and entity-specific requirements, including Delaware franchise tax, 1099s, Form 5472, and nexus-related workflows.
• - Partner with product and engineering to turn accounting rules into product logic, including categorization, double-entry treatment, and exception handling.
• - Review messy real-world cases—such as Stripe payouts, intercompany transfers, and personal-business expense overlap—and help improve the system every week.
• - Support early customers through onboarding and questions, then bring what you learn back into the product.
• - Help create accounting policies, quality checks, and review process.

You will have support and escalation paths for complex technical matters. We do not expect you to know everything on day one; we do expect you to be thoughtful, rigorous, and eager to learn fast.

What we're looking for

• 1.5–4 years of hands-on U.S. accounting and/or tax experience.
• - Experience with bookkeeping, reconciliations, closes, tax filings, or supporting client accounts.
• - Interest in startups, automation, and how software can improve accounting work.
• - Strong attention to detail and sound judgment about when to ask for help.
• - Clear written communication—you can explain a complex issue in plain language.
• - Comfort with ambiguity and working directly with founders and customers.
• - CPA or EA is welcome but not required.
• - Experience with Delaware entities, Form 5472, Stripe, sales-tax nexus, or foreign-owned entities is a plus, not a requirement.

Why this role
You'll build a rare skill set at the intersection of tax, accounting, product, and AI.
As we grow, this role can grow into leading the accounting and tax function, owning larger parts of product strategy, and building the team behind it. Your judgment will not be spent one client at a time—it will be built into the product.

What it's like to work here
This is early. The product is still being built, priorities will move, and there will be busy stretches around launch and filing deadlines.
If you want a fixed, highly structured role, this may not be the right fit. If you want a steep learning curve, real ownership, and a front-row seat to building a new kind of accounting company, we'd love to hear from you.

How to apply
Skip the cover letter. In a few paragraphs, tell us about a tax or accounting judgment call you found interesting. What were the facts, what did you decide, and what information would a system need to make that decision well?
Email: [email protected]