Bookkeeper

Topkey is a pioneering financial automation platform specifically designed for vacation rental managers. Our platform seamlessly integrates with property management systems (PMS) and accounting software, offering a unified solution that automates financial processes including expenses, bookkeeping, receipts, banking, corporate cards, accounts payable, and bill payments. Backed by prominent investors such as Felicis Ventures, Andreessen Horowitz (a16z), and Y Combinator, Topkey is a leading emerging startup in the vertical SaaS space with a rapidly growing trajectory. We address the unique financial management needs of the $110 billion hospitality market, helping property managers increase profitability by reducing cash leakage and streamlining workflows. Our solutions have been featured in Axios, Wall Street Journal, Fortune, and other media outlets.

About the role

We are seeking a detail-oriented and proactive Bookkeeper with experience in short-term rental or property management to join our dynamic team. In this role, you will manage day-to-day financial records at the property level, ensuring accuracy and timeliness in bookkeeping processes. You will collaborate with our product development team to improve accounting workflows and assist with financial tasks that support our clients’ operational efficiency. This position is ideal for someone early in their career who is familiar with short-term rental books, eager to develop their skills within a growing fintech environment, and interested in modern accounting tools. Your contributions will directly impact the accuracy of financial data and the overall success of our platform’s automation capabilities.

Responsibilities

• Categorize transactions accurately and reconcile accounts regularly to ensure books are current
• Process accounts payable and receivable efficiently
• Assist with month-end closing activities, including ledger reviews and anomaly detection
• Maintain owner ledgers and property-specific financial records
• Prepare owner statements and supporting financial reports
• Perform data entry, documentation, and organize files meticulously
• Identify recurring issues or workflow friction points for continuous improvement
• Collaborate with senior accounting team members on cleanup and onboarding projects

Requirements

• 1-3 years of bookkeeping experience, preferably within short-term rental, vacation rental, or property management sectors
• Proficiency with QuickBooks Online
• Some experience with property management software (PMS) such as Guesty, Track, Hostaway, Streamline, OwnerRez, Rentvine, Hostfully, or similar platforms (preferred)
• Strong Excel skills
• Exceptional attention to detail and organizational abilities
• Responsive and proactive communication style
• Willingness to ask questions and learn quickly
• Fluent in English (B2+ level)
• Availability during U.S. business hours
• Ability to work as an independent contractor

Benefits

• Competitive compensation based on experience
• Remote work flexibility
• Paid time off to support work-life balance
• Opportunity for meaningful growth alongside experienced accountants and a technical team developing next-generation property management financial tools