Bookkeeper (Founding Member)

About the 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'll own end-to-end bookkeeping for a portfolio of pilot restaurant customers, serve as Toast's in-house expert on restaurant-specific accounting, and embed directly with product and engineering to shape the service, tooling, and workflows.

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.
• Design and document the SOPs, controls, and QA processes a bookkeeping function needs to run reliably.
• 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.

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 including experience working with AI tools, Claude, GPT, Gemini, etc.
• An entrepreneurial track record — you've 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; 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

• 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.

Benefits

Our total rewards package includes base salary, cash compensation (overtime, bonus/commissions if eligible), equity, and benefits. You can learn more about our benefits at https://careers.toasttab.com/toast-benefits.

Pay Range

The base salary range for this role is $79,000—$126,000 USD.

How Toast Uses AI In Its Hiring Process

We use AI tools to support our recruiters and interviewers with tasks like note-taking, summarization, and documentation of interviews to ensure they can be fully focused on your conversation. All hiring decisions are made by people.

Our Approach to Hybrid Working

We embrace a hybrid work model that fosters in-person collaboration while valuing individual needs. Our goal is to build a strong culture of connection as we work together to empower the restaurant community.

Diversity, Equity, and Inclusion

We embrace diversity, equity, and inclusion with authenticity, inclusivity, respect, and humility. By embedding these principles into our culture and design, we create equitable opportunities for all and raise the bar in delivering exceptional experiences.

Apply Today!

Toast is committed to creating an accessible and inclusive hiring process. If you need an accommodation to access the job application or interview process, please contact candidateaccommodations@toasttab.com. For roles in the United States, it is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment.