About Topkey

Topkey 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 Role

This 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 Do

• Own full-cycle accounting work including AP/AR, bank and credit card reconciliations, and month-end close
• Prepare and review monthly financial statements, management reports, and cash flow analysis
• Handle property-level accounting workflows including owner ledgers, owner statements, and trust account activity
• Perform 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 processes
• Partner with product and engineering to surface workflow gaps, design better accounting logic, and pressure-test new features before they ship
• Serve as an internal subject-matter expert on STR and vacation rental accounting
• Ensure compliance with U.S. GAAP and relevant regulations

Qualifications:

• 3+ years of accounting experience, with direct experience in short-term rental, vacation rental, or property management accounting
• Strong working knowledge of QuickBooks Online; experience with Sage, Xero, or NetSuite a plus
• Hands-on experience with at least one major PMS (Guesty, Track, Hostaway, Streamline, OwnerRez, Rentvine, Hostfully, AppFolio)
• Familiarity with trust accounting concepts and owner statement workflows
• Advanced Excel
• Sharp, detail-oriented, and comfortable operating independently in a fast-moving environment
• Genuinely willing to operate across both advisory and execution work, not just one
• Fluent English (B2+)
• Availability during U.S. business hours
• Works as an independent contractor

Benefits:

• Competitive pay based on experience
• Remote
• Paid time off
• Direct exposure to a fast-growing AI-native fintech platform and the chance to shape how modern property management accounting gets done

How to Apply:

In 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.