Bookkeeper (Founding Member)

<p>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.</p> <p><strong>About This Role</strong></p> <p>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.</p> <p>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.&nbsp; Ambiguity here isn't a bug; for the first year or two, it's the job.</p> <p>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.</p> <p><strong>*Location Requirement: </strong>This position requires 2 days per week on-site at our Boston office (located in the Seaport).&nbsp;</p> <p><strong>A day in the life (Responsibilities)&nbsp;</strong></p> <ul> <li>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.</li> <li>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.</li> <li>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.</li> <li>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.</li> <li>Work directly with restaurant operators to understand their businesses, set expectations, and deliver a service that earns their trust.</li> <li>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.</li> <li>Move fluidly between hands-on bookkeeping work and higher-leverage building work as priorities shift — comfort wearing both hats is essential.</li> </ul> <p><strong>What you'll need to thrive (Requirements)</strong></p> <ul> <li>5+years of bookkeeping experience, with meaningful time spent on restaurant or hospitality clients specifically.</li> <li>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.</li> <li>Fluency with modern bookkeeping and accounting software, and genuine enthusiasm for adopting new tools.</li> <li>Experience building a process or practice from scratch.&nbsp;</li> <li>Genuine comfort with ambiguity and undefined scope; you'd rather help define a role than be handed a finished one.</li> <li>Strong communication skills — able to translate accounting complexity into plain language for both restaurant operators and internal product/engineering partners.</li> <li>Sharp attention to detail and the organizational discipline to manage multiple clients' books accurately and on schedule.</li> </ul> <p><strong>What will help you stand out (Nonessential Skills/Nice to Haves)&nbsp;</strong></p> <ul> <li>Experience at a tech startup, in professional se