Customer Support — Financial Software

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

We're looking for a customer support specialist with strong English communication skills to join the team. You'll be the first point of contact for property managers who have questions, run into issues, or need help getting the most out of the platform — and you'll work closely with our CS and product teams to make sure those experiences are consistently excellent.

This is a strong fit for someone with a background in SaaS or fintech support who is organized, proactive, and genuinely invested in helping customers succeed. Experience with financial technology or property management software is a plus, not a requirement.

What You’ll Do

• Serve as the primary point of contact for inbound customer questions via chat and email
• Troubleshoot issues with transactions, integrations, card management, and accounting workflows — and escalate clearly when needed
• Document bugs and customer-reported issues in structured, actionable formats for the engineering and CS teams
• Maintain and improve internal and external help documentation so customers can self-serve common questions
• Monitor customer health signals and flag at-risk accounts before issues escalate
• Surface recurring friction points and patterns to help improve workflows at the product level

Qualifications:

• 2+ years in a customer support or customer success role, ideally at a SaaS or fintech company
• Excellent written and spoken English — this role requires clear, professional communication with U.S.-based customers (C1 level minimum)
• Organized, responsive, and proactive — you manage your own queue and follow up without being asked
• Comfortable breaking down technical issues and explaining them clearly to both customers and internal teams
• Experience with helpdesk or support tools (Plain, Intercom, Zendesk, Linear, or similar)
• Familiarity with financial technology, accounting workflows, or property management software is a strong plus
• Availability during U.S. business hours
• Works as an independent contractor

Benefits:

• Competitive pay based on experience
• Remote
• Paid time off
• Meaningful growth path alongside a CS and technical team building the next generation of property management financial tools

How to Apply:

In your application, include 2–3 sentences describing a customer issue you resolved that required technical troubleshooting, and what tools or process you used. Applications without directly relevant support 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.