Accountant / Bookkeeper — Short-Term Rental / Property Management

About TopkeyTopkey is the leading financial automation platform built specifically for vacation rental managers. Integrating directly into your PMS and accounting software, Topkey provides a single, unified system that automates expenses, bookkeeping, receipts, banking*, corporate cards, AP/bill pay, and more.Topkey partners with numerous vacation rental property managers to increase profitability by eliminating cash leakage and automating time-consuming financial workflows. As the only expense platform in the property management industry with direct integrations to Visa, American Express, and Mastercard, Topkey delivers unmatched accuracy, flexibility, and confidence over your expenses. See what our customers say about using Topkey at topkey.io/customers.We’re backed by top-tier investors like Felicis Ventures, Andreessen Horowitz (a16z), and Y Combinator. Topkey is recognized as one of the top emerging vertical startups, and our trajectory is steep. We’re looking for driven individuals to join our team and help shape the future of financial infrastructure in the $110 billion hospitality market.We’ve been featured in numerous media outlets, including Axios, Wall Street Journal, Fortune, Phocuswire, Short Term Rentalz, and Fintech Global.About The RoleThis is a hybrid role with two sides to it.On one side, you'll work closely with our product and engineering teams as a subject-matter expert, helping us sharpen the accounting workflows we're building, from owner statements to trust reconciliation to revenue recognition. Your day-to-day experience with the real pain of STR accounting will directly shape what we ship.On the other side, you'll be in the work. That means hands-on accounting execution: reconciliations, close, owner ledgers, cleanup, edge cases. We believe the only way to build great accounting software is to stay close to the actual craft, and we need someone who's genuinely comfortable going back and forth between "how should this workflow function" and "let me just do the workflow."If you want to sit in a corner and only give opinions, this isn't the role. If you want to apply deep STR accounting expertise to both improve a product and deliver real work, keep reading.What You’ll DoOwn full-cycle accounting work including AP/AR, bank and credit card reconciliations, and month-end closePrepare and review monthly financial statements, management reports, and cash flow analysisHandle property-level accounting workflows including owner ledgers, owner statements, and trust account activityPerform revenue reconciliation across PMS platforms (Guesty, Track, Hostaway, Streamline, OwnerRez, and others) and accounting systems (QBO, Sage, Xero)Support trust accounting and three-way reconciliation processesPartner with product and engineering to surface workflow gaps, design better accounting logic, and pressure-test new features before they shipServe as an internal subject-matter expert on STR and vacation rental accountingEnsure compliance with U.S. GAAP and relevant regulationsQualifications3+ years of accounting experience, with direct experience in short-term rental, vacation rental, or property management accountingStrong working knowledge of QuickBooks Online; experience with Sage, Xero, or NetSuite a plusHands-on experience with at least one major PMS (Guesty, Track, Hostaway, Streamline, OwnerRez, Rentvine, Hostfully, AppFolio)Familiarity with trust accounting concepts and owner statement workflowsAdvanced ExcelSharp, detail-oriented, and comfortable operating independently in a fast-moving environmentGenuinely willing to operate across both advisory and execution work, not just oneBenefitsCompetitive pay based on experienceRemotePaid time offDirect exposure to a fast-growing AI-native fintech platform and the chance to shape how modern property management accounting gets doneHow To ApplyIn your application, include 2–3 sentences specifically describing your experience reconciling PMS data against a general ledger and any STR or vacation rental accounting work you've done. Applications without directly relevant experience will not be prioritized.Topkey is a financial technology company and is not an FDIC-insured bank. Banking services provided by Thread Bank, Member FDIC.