Guesty: Shield Program Lead

Headquarters: Canada

URL: https://www.guesty.com

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 Shield Program Lead to take end-to-end ownership of the operations and ongoing performance of Guesty Shield globally. You will lead the internal claims team, manage commercial relationships with insurers and program partners, and ensure customers receive a reliable experience from enrollment through claims resolution and payment. You will drive improvements in customer retention, operational efficiency and program profitability, while leading new product launches and improvements alongside Product and other internal teams. This is a hands-on role for someone with experience in the short-term rental/vacation rental industry who can manage people, lead commercial discussions and follow through on operational details.

01Responsibilities

Program Operations

Own the day-to-day operation of Shield across all active markets, with clear processes, accountability and consistent service delivery. Establish reporting, controls and escalation procedures, and resolve recurring operational issues. Drive automation and process improvements that enable the program to scale efficiently. Maintain visibility into program performance, risks and action plans.

Team Leadership and Claims Oversight

Manage and develop the internal claims team, including workload allocation, coaching, performance management and quality assurance. Oversee the claims journey from submission through decision and payment of approved claims, in coordination with insurers and claims partners. Establish and monitor service levels, ensuring timely customer communication and payment. Resolve overdue claims and complex escalations, holding partners accountable for agreed commitments. Ensure claims are handled accurately and consistently with applicable coverage terms.

Customer Retention

Own Shield retention performance and lead initiatives to reduce churn in partnership with Customer Success. Identify cancellation drivers and early signs of dissatisfaction, and translate findings into corrective actions. Address retention issues related to pricing, coverage, claims experience and service delivery. Distinguish Shield-specific cancellations from broader Guesty churn, and monitor reductions in coverage among existing customers.

Commercial Partnerships and Program Economics

Own ongoing relationships with insurers, claims administrators and other program partners. Lead commercial discussions, renewals, performance reviews and escalations, coordinating with Finance and Legal. Negotiate improvements to commercial terms, service levels and operating processes. Track program revenue, margins and operating costs with Finance, and identify opportunities to improve profitability while maintaining service and coverage quality. Manage partner transitions and ensure continuity of service.

02Requirements

Must

Prior experience in the short-term rental (STR) / vacation rental industry, with a strong understanding of property manager operations, guest-related damage and protection needs. 5+ years of relevant experience in program management, insurance or protection programs, operations, or a closely related field. Proven experience directly managing and developing an operational team. Experience managing insurers or insurance partners, including commercial negotiations and service performance. Strong understanding of claims workflows, customer service and operational controls. Commercial and analytical judgment, with the ability to use data to improve retention, profitability and service quality. A track record of leading cross-functional initiatives from planning through implementation. Strong communication, negotiation and problem-solving skills. Ability to work across markets and time zones and take ownership in a fast-moving environment.

03Preferred Qualifications

Experience in embedded insurance or property protection programs. Experience managing international programs and partner relationships. Experience implementing workflow automation, operational dashboards or claims management systems.

Please note that this is a Remote position __________ Compensation range: 120-140K OTE annually Exact compensation may vary based on skills, experience, and location.-

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. To apply: https://weworkremotely.com/remote-jobs/guesty-shield-program-lead