Shield Program Lead

Responsibilities: Program Operations: — Manage daily operations of the Shield program across all active markets ensuring clear processes, accountability, and consistent service delivery. — Establish reporting, controls, escalation procedures, and resolve recurring operational issues. — Drive automation and process improvements to enable efficient program scaling. — Maintain visibility into program performance, risks, and action plans. Team Leadership and Claims Oversight: — Lead and develop the internal claims team including workload allocation, coaching, performance management, and quality assurance. — Oversee the claims process from submission to decision and payment, coordinating with insurers and claims partners. — Establish and monitor service levels to ensure timely customer communication and payment. — Resolve overdue claims and complex escalations, holding partners accountable. — Ensure claims are handled accurately and consistently with coverage terms. Customer Retention: — Own Shield retention performance and lead initiatives to reduce churn in partnership with Customer Success. — Identify cancellation drivers and early dissatisfaction signs, translating findings into corrective actions. — Address retention issues related to pricing, coverage, claims experience, and service delivery. — Differentiate Shield-specific cancellations from broader Guesty churn and monitor coverage reductions. Commercial Partnerships and Program Economics: — Manage ongoing relationships with insurers, claims administrators, and program partners. — Lead commercial discussions, renewals, performance reviews, and escalations in coordination with Finance and Legal. — Negotiate improvements to commercial terms, service levels, and operating processes. — Track program revenue, margins, and operating costs with Finance, identifying profitability improvement opportunities. — Manage partner transitions ensuring continuity of service. Requirements: — Prior experience in short-term rental/vacation rental industry with strong understanding of property manager operations and protection needs. — 5+ years relevant experience in program management, insurance or protection programs, operations, or related fields. — Proven experience managing and developing operational teams. — 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 ability to use data to improve retention, profitability, and service quality. — 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. Preferred 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. Benefits: — Remote position. — Compensation range: 120-140K OTE annually, exact compensation varies based on skills, experience, and location. Guesty is an Equal Opportunity Employer providing equal employment opportunities regardless of race, color, religion, sex, age, national origin, disability, veteran status, pregnancy, sexual orientation, or any other protected characteristic.