Bookkeeper (Founding Member)

What you'd do

• Own end-to-end bookkeeping for a portfolio of pilot restaurant customers: chart of accounts setup, monthly close, bank/POS reconciliations, accruals, and delivery of clean financial statements.
• Serve as Toast's in-house expert on restaurant-specific accounting — prime cost, COGS, labor and tip reporting, multi-unit consolidation, high-volume daily transaction reconciliation, and multi-jurisdiction sales tax.
• Embed directly with product and engineering, translating real client workflows and pain points into product requirements that shape our roadmap — you'll be in the room when we decide what to build next, not just told what shipped.
• Design and document the SOPs, controls, and QA processes a bookkeeping function needs to run reliably — since none of it exists yet, you'll build the foundation others will scale on.
• Work directly with restaurant operators to understand their businesses, set expectations, and deliver a service that earns their trust.
• Help define what “great” looks like for this function as it grows, including future hiring needs, tooling choices, and where automation should (and shouldn't) replace judgment.
• Move fluidly between hands-on bookkeeping work and higher-leverage building work as priorities shift — comfort wearing both hats is essential.

What they want

• 5+years of bookkeeping experience, with meaningful time spent on restaurant or hospitality clients specifically.
• Deep working knowledge of restaurant accounting mechanics: COGS and prime cost, tip pooling and reporting, multi-location consolidation, and reconciling high-volume POS transaction data.
• Fluency with modern bookkeeping and accounting software, and genuine enthusiasm for adopting new tools.
• Experience building a process or practice from scratch.
• Genuine comfort with ambiguity and undefined scope; you'd rather help define a role than be handed a finished one.
• Strong communication skills — able to translate accounting complexity into plain language for both restaurant operators and internal product/engineering partners.
• Sharp attention to detail and the organizational discipline to manage multiple clients' books accurately and on schedule.
• Experience at a tech startup, in professional services, or inside an embedded finance / fintech environment.
• Prior exposure to Toast POS or other restaurant management systems.
• Experience working with AI tools (ie - Claude, GPT, Gemini, etc.)

About Toast · Customer Success : Customer Care : Supplier & Accounting

We're hiring the first Bookkeepers on our Financial Management team — a founding, hands-on role at the intersection of real client bookkeeping and 0-to-1 product building. You won't be joining an established practice with a mature playbook; you'll be writing it. You'll do the actual books for our earliest restaurant customers while working shoulder-to-shoulder with product and engineering to shape the service, tooling, and workflows that will define how Toast delivers bookkeeping at scale. This…