Bookkeeper + Tax Help

About BostonSpeaks BostonSpeaks helps professionals overcome public speaking anxiety through coaching, courses, workshops, and digital education. We're a growing, financially disciplined small business, and we're looking for a reliable bookkeeper who can also keep us on top of our S-corp tax obligations and give us confidence in our numbers. This is an ongoing, part-time contract role. We value people who take ownership, communicate clearly, and treat our numbers with the same care we'd give them ourselves. What You'll Do You'll own our day-to-day bookkeeping and help us stay ahead of our tax obligations. Bookkeeping (QuickBooks Online) - Categorize transactions and reconcile accounts monthly - Keep income, expenses, and owner activity accurately recorded - Deliver clean monthly financials (P&L, balance sheet, cash flow) we can actually trust - Keep our chart of accounts organized and consistent - Flag discrepancies, unusual activity, or anything that doesn't look right, before it becomes a problem S-Corp Quarterly Estimates (and potential future Tax work) - Calculate and prepare quarterly estimated tax payments for our S-corp (one entity), so there are no year-end surprises - Help us understand our estimated tax liability throughout the year so we can plan cash flow - Review reasonable owner compensation (W-2 salary vs. distributions) and flag anything that needs attention - Make sure owner payroll and distributions are accounted for correctly - Coordinate with our tax preparer at year-end (or file/coordinate the 1120-S if you're qualified) - Answer our finance and S-corp tax questions in plain English Who We're Looking For - Solid bookkeeping experience, ideally with U.S. small businesses - Strong working knowledge of QuickBooks Online - Experience with S-corp taxes and quarterly estimated payments (reasonable comp, distributions vs. payroll, etc.) - Detail-oriented and accurate—you double-check your work - Clear, proactive communicator who responds promptly - Trustworthy and discreet with sensitive financial information - Comfortable working independently and managing recurring deadlines Nice to Have - CPA, EA, or bookkeeping certification (QuickBooks ProAdvisor a plus) - Experience with coaching, education, or service-based businesses - Familiarity with Profit First or similar cash-management frameworks - Experience working with an external tax preparer / collaborating on year-end filings We're looking for a long-term partner, not a one-off project. To Apply Step 1: Reply to us here on Upwork with a short message telling us: Your experience with QuickBooks Online and S-corps Your availability and quote for work. Any relevant certifications Step 2: Record a short Loom video (about 2 minutes) answering these questions: Briefly introduce yourself and your bookkeeping/tax background. Why you? What do you know about us? Paste the Loom link in your Upwork reply. Applications without a Loom video won't be considered. We review every application and reply to those who are a strong fit. We look forward to hearing from you.