Trust Accounting Specialist

Guesty is the all-in-one platform helping hospitality businesses around the world automate, optimize, and scale their operations. We’re a fast-growing global startup that’s transforming how the industry works — from guest experience to business growth.

With a powerful suite of features and integrations with 150+ industry partners — including Airbnb, Vrbo, Booking.com, Expedia, Google Travel, and many more — Guesty empowers property managers to deliver top-tier guest experiences while running more efficient, data-driven operations.

We’re proud to have over 900+ team members across 16 countries worldwide, all working together to build the future of hospitality technology.

If you’re looking to grow your career in a dynamic, global, and impact-driven environment, we’d love to hear from you. 

We are looking for a Accounting Technical Program Manager to join our team. This role is open to candidates based remotely in Canada or the United States. Candidates located in the New York area will follow a hybrid schedule, with an expectation to work from our New York office two days per week.

We are creating a dedicated Trust Accounting Specialist position to act as the subject matter expert (SME) during high-stakes sales conversations. In this role, you will bridge the gap between complex financial practices and sales demos. You will own the narrative around how Trust Accounting functions primarily, but not limited to, the US vacation rental market, guiding prospective clients through step-by-step product capabilities—focusing on actual day-to-day operations and critical end-of-month financial flows.

• Sales Collaboration & Customer Demos: Partner with Account Executives and Market Managers during sales calls to lead deep-dive product demonstrations focused specifically on Guesty’s Trust Accounting features.
• Operational Flow Walkthroughs: Clearly present and explain day-to-day workflows (e.g., owner payouts, trust liability tracking, reservation split logic, management fee realization, bank reconciliation) and end-of-month closing/reconciliation processes.
• Domain Leadership: Serve as Guesty’s internal and external subject matter expert on US vacation rental trust accounting regulations, industry practices, and compliance standards.
• Objection Handling & Technical Translation: Address technical financial questions, objections, and compliance concerns from prospective clients' CFOs, operational managers, and accountants.
• Sales Enablement & Training: Develop pitch guidance, cheat sheets, and internal documentation to help the broader sales team confidently speak to basic trust accounting concepts and qualification questions.
• Product Feedback Loop: Partner with Product Management and Engineering by sharing real-time market feedback and customer pain points regarding trust accounting workflows.

• Industry Expertise: Deep familiarity with the US vacation rental, hospitality, or short-term rental industry.
• Financial Domain Knowledge: Strong understanding of Trust Accounting principles, regulatory standards in key US markets, trust bank reconciliation, owner payout structures, and month-end accounting cycles.
• Customer-Facing Experience: Experience in a solutions consultant, customer success, account management, sales enablement, or property management accounting role.
• Technical Aptitude: Comfort navigating complex software platforms and mapping real-world accounting processes to SaaS platform workflows without needing a software engineering background.
• Communication Skills: Exceptional ability to explain intricate financial mechanics in plain, persuasive language to both non-technical property managers and detail-oriented financial leaders.

Preferred Qualifications

• Prior experience with property management software (PMS) trust accounting modules (e.g., Guesty, Streamline, Track, Escapia, or similar platforms).
• Background as a property manager, trust accountant, or financial coordinator in the US vacation rental sector - bonus.

Why Join Guesty?

• Be a key strategic voice in transforming how Guesty demonstrates value to mid-market and enterprise property managers.
• Work closely with a global team in a fast-paced, high-growth prop-tech company.
• Competitive salary, benefits package, and opportunities for professional growth.

Guesty is proud to be an Equal Opportunity Employer. We provide equal employment opportunities to all employees and applicants regardless of race, color, religion, sex, age, national origin, disability, veteran status, pregnancy, sexual orientation, or any other characteristic protected by law.