Trust Accounting Specialist

Guesty•USA, NY

4h•Remote

About The Position

Guesty is creating a dedicated Trust Accounting Specialist position to serve as a subject matter expert during high-stakes sales conversations. The role bridges complex financial practices and sales demonstrations, owning the explanation of how trust accounting works primarily in the US vacation rental market. The specialist guides prospective clients through product capabilities step by step, with a focus on day-to-day operations and end-of-month financial flows. The position is open to candidates based remotely in Canada or the United States. Candidates located in the New York area are expected to work from Guesty’s New York office two days per week.

Requirements

Deep familiarity with the US vacation rental, hospitality, or short-term rental industry.
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 in a solutions consultant, customer success, account management, sales enablement, or property management accounting role.
Comfort navigating complex software platforms and mapping real-world accounting processes to SaaS workflows; a software engineering background is not required.
Exceptional ability to explain intricate financial mechanics in clear, persuasive language to non-technical property managers and detail-oriented financial leaders.

Nice To Haves

Prior experience with property management software trust accounting modules, such as Guesty, Streamline, Track, Escapia, or similar platforms.
Background as a property manager, trust accountant, or financial coordinator in the US vacation rental sector.

Responsibilities

Partner with Account Executives and Market Managers during sales calls to lead in-depth demonstrations of Guesty’s Trust Accounting features.
Explain day-to-day workflows such as owner payouts, trust liability tracking, reservation split logic, management fee realization, and bank reconciliation, as well as month-end closing and reconciliation processes.
Serve as Guesty’s internal and external subject matter expert on US vacation rental trust accounting regulations, industry practices, and compliance standards.
Address technical financial questions, objections, and compliance concerns from prospective clients, including CFOs, operational managers, and accountants.
Develop pitch guidance, cheat sheets, and internal documentation to help the sales team discuss basic trust accounting concepts and qualification questions.
Share market feedback and customer pain points about trust accounting workflows with Product Management and Engineering.