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

Were 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 wont be joining an established practice with a mature playbook; youll be writing it. Youll 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 isnt a bug; for the first year or two its the job.

If youre the kind of person who reads a messy set of restaurant books and sees an interesting puzzle and whod rather build the recipe than follow one wed 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 Toasts 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 youll 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 youll 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 shouldnt) replace judgment.
• Move fluidly between hands-on bookkeeping work and higher-leverage building work as priorities shift comfort wearing both hats is essential.

What youll need to thrive (Requirements)

• 5years 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 including experience working with AI tools Claude GPT Gemini etc.
• An entrepreneurial track record youve built a client base a process or a service from scratch before rather than only operating inside an existing one.
• Genuine comfort with ambiguity and undefined scope; youd 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.
• A CPA CB or equivalent bookkeeping/accounting credential.

AI at Toast

At Toast one of our company values is that were 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; its 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 base salary range for this role is listed below. The starting salary will be determined based on skills experience and geographic addition to base salary our total rewards components include cash compensation (overtime bonus/commissions if eligible) equity and benefits. You can learn more about how we align pay with local labor markets in our Geographic Pay Zone Philosophy.