About this role.
Toast is hiring a founding Bookkeeper to own end-to-end accounting for pilot restaurant customers while helping design a scalable bookkeeping service. The role covers monthly close, bank and POS reconciliations, accruals, financial statements, multi-location consolidation, tip reporting, and sales-tax complexity. This person will work closely with restaurant operators as well as product and engineering teams to translate operational problems into workflows, tooling, and product requirements. Success requires deep restaurant-accounting expertise, meticulous client-service execution, and comfort building SOPs and controls in an ambiguous early-stage environment.
Role DNA
A quick view of the complexity, pace, ownership and collaboration implied by the job description.
Job Complexity
5/5Pace & Pressure
5/5Autonomy Level
5/5Communication Load
5/5Salary analysis
Estimated compensation compared with the broader US market for similar roles.
Core skills
Skills and capabilities most closely associated with this opportunity.
Sample interview questions
I would first establish the accounting periods, chart of accounts, source systems, bank and POS access, and outstanding-data gaps. I would prioritize reconciliations of cash, bank, credit card, POS settlement, payroll, and major liabilities, then document assumptions and corrections in a clear close checklist. Once the historical books are reliable, I would establish a repeatable monthly close calendar and client communication cadence.
Key controls include daily reconciliation of POS sales to payment processor deposits, separation of sales, tax, tips, discounts, refunds, and gift-card activity, and documented exception handling for timing differences. I would also reconcile delivery-platform settlements and chargebacks independently, retain audit-ready support, and use automated matching only with review thresholds for unusual variances.
I would describe the user, workflow stage, current inputs, decision points, exception paths, and measurable impact of the problem. For example, rather than asking for a generic reconciliation feature, I would specify how the system should ingest POS and processor data, identify expected settlement timing, surface unmatched transactions, and preserve an audit trail. I would validate the proposed workflow with bookkeepers and restaurant operators before treating it as complete.
I would explain that prime cost is the combined cost of food, beverages, and labor required to produce sales, and frame the variance in operational terms. I would show the period-over-period drivers, such as higher ingredient costs, overtime, waste, discounting, or sales mix, then identify the few actions most likely to improve the result. The goal is to make the financial statement actionable rather than simply technically correct.
I use standardized close checklists, clear ownership, documented deadlines, and risk-based review procedures for every client. I triage work by customer impact, reporting deadlines, and control risk, while communicating early when a dependency could affect delivery. I also document recurring exceptions and process improvements so that urgent work becomes less manual over time.
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.
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.
The base salary range for this role is listed below. The starting salary will be determined based on skills, experience, and geographic location. In 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.
Zone A
$91,000—$146,000 USD
Zone B
$79,000—$126,000 USD
Zone C
$72,000—$115,000 USD
How Toast Uses AI in its Hiring Process
Throughout the hiring process, our goal is to get to know you. 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. We ask that you complete interviews and assessments on your own, without real-time AI tools, recording, or transcription bots, unless we tell you otherwise in advance. To learn more: https://careers.toasttab.com/ai-in-hiring
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 hospitality community, regardless of location. Please visit the Locations page on our career site to learn more about our in-office expectations by region: https://careers.toasttab.com/locations-toast
People Are the Secret Ingredient in Our Recipe for Success
At Toast, our employees are our secret ingredient—when they thrive, we thrive. The restaurant industry brings together people with a wide range of backgrounds, experiences, and perspectives, and we value that same breadth at Toast. We strive to build a culture grounded in authenticity, respect, and humility, where every Toaster has a real opportunity to grow, contribute, and do their best work—raising the bar in delivering exceptional experiences for our customers and each other.
We Thrive Together
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. To learn more about how we work globally and regionally, check out: https://careers.toasttab.com/locations-toast.
Apply today!
Toast is committed to creating an accessible and inclusive hiring process. As part of this commitment, we strive to provide reasonable accommodations for persons with disabilities to enable them to access the hiring process. If you need an accommodation to access the job application or interview process, please contact candidateaccommodations@toasttab.com.
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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. An employer who violates this law shall be subject to criminal penalties and civil liability.
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