Bookkeeper (Founding Member)

Toast creates technology to help restaurants and local businesses succeed in a digital world, helping business owners operate, increase sales, engage customers, and keep employees happy.

About This Role

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 role is for someone who genuinely likes restaurant bookkeeping — the prime cost, the tip reporting, the multi-location chaos — and who also gets energy from questioning industry norms and building something new rather than maintaining something established.  Ambiguity here isn't a bug; for the first year or two, it's the job.

If you're the kind of person who reads a messy set of restaurant books and sees an interesting puzzle — and who'd rather build the recipe than follow one — we'd love to hear from you.

*Location Requirement: This position requires 2 days per week on-site at our Boston office (located in the Seaport). 

A day in the life (Responsibilities) 

• 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 you'll need to thrive (Requirements)

• 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.

What will help you stand out (Nonessential Skills/Nice to Haves) 

• 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.)
• A CPA, CB, or equivalent bookkeeping/accounting credential.

AI at Toast

At Toast, one of our company values is that we're hungry to build and learn. We believe learning new AI tools empowers us to build for our customers faster, more independently, and with higher quality. We provide these tools across all disciplines, from Engineering and Product to Sales and Support, and are inspired by how our Toasters are already driving real value with them. The people who thrive here are those who embrace changes that let us build more for our customers; it’s a core part of our culture.

Our Total Rewards Philosophy

We strive to provide competitive compensation and benefits programs that help to attract, retain, and motivate the best and brightest people in our industry. Our total rewards package goes beyond great earnings potential and provides the means to a healthy lifestyle with the flexibility to meet Toasters’ changing needs. Learn more about our benefits at https://careers.toasttab.com/toast-benefits.