PitchMeAI Jobs
Toast

Bookkeeper (Founding Member)

Toast · Boston, MA

Posted about 2 months ago

or apply directly on Toast's site. We never take the application ourselves.

Is this posting real?

This role has been open
53 days
Toast's roles stay open a median of 51 days
Reposted
No
Salary listed
No
0% of Toast's roles list one
Ghost-job risk at Toast
high
189 stale, 57 reposted of 346 open
Hiring momentum
625 roles opened in the last 90 days
↑ up vs. the prior 90 days
Last confirmed on the employer's board
2026-09-26

Measured from postings appearing on and disappearing from Toast's own greenhouse board since 2026-08-03. Full hiring picture for Toast.

About this role

As a Bookkeeper at Toast, you'll manage the bookkeeping for a portfolio of restaurant clients, handling everything from chart of accounts setup to delivering financial statements. This role involves collaborating closely with product and engineering teams to shape the bookkeeping service and define processes from scratch, all while navigating the unique challenges of the restaurant industry. You'll need to be comfortable with ambiguity and enjoy building new systems rather than following established ones.

Our read on this posting2.2out of 5
benefits
2/5
freshness
1/5
career value
4/5
role clarity
4/5
pay transparency
0/5

Scored from the posting itself — how clearly the role is described, how much it says about pay and benefits, and how recently it was listed. Not a judgement of Toast as an employer.

What you need

  • 5+ years of bookkeeping experience, specifically with restaurant or hospitality clients
  • Deep working knowledge of restaurant accounting mechanics including COGS, prime cost, and multi-location consolidation
  • Fluency with modern bookkeeping and accounting software
  • Experience building a process or practice from scratch
  • Genuine comfort with ambiguity and undefined scope
  • Strong communication skills to translate accounting complexity

Nice to have

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

What you get

  • Competitive compensation and benefits programs
  • Cash compensation including overtime, bonus/commissions if eligible
  • Equity opportunities
  • Flexible benefits to meet changing needs

Worth weighing

  • Role involves significant ambiguity and undefined scope
  • Position requires 2 days per week on-site in Boston
  • No specific mention of a structured onboarding process or existing playbook
  • Work may involve a mix of hands-on bookkeeping and higher-leverage building tasks

Summarised from Toast's posting. Read the full original.

Listed by Toast on their greenhouse job board, last confirmed open on 2026-09-26. PitchMeAI is not the employer.

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