Shield Program Lead

This is a fully remote position, open to applicants in Canada.

📋 Description

• Take charge of the daily operations of Shield across all active markets, ensuring clear processes, accountability, and consistent service delivery.

• Develop reporting, control measures, and escalation procedures while addressing recurring operational challenges.

• Propel automation and process enhancements that facilitate efficient scaling of the program.

• Maintain oversight of program performance, risks, and actionable plans.

• Lead and nurture the internal claims team, focusing on workload distribution, coaching, performance management, and quality assurance.

• Supervise the claims process from submission to the decision and payment of approved claims, in collaboration with insurers and claims partners.

• Set and monitor service standards to ensure timely communication with customers and prompt payment.

• Resolve overdue claims and complex escalations, ensuring partners adhere to their commitments.

• Guarantee accurate handling of claims in accordance with applicable coverage terms.

• Take ownership of Shield retention performance and spearhead initiatives to minimize churn in collaboration with Customer Success.

• Identify factors leading to cancellations and early indicators of dissatisfaction, converting insights into corrective actions.

• Address retention challenges related to pricing, coverage, claims experiences, and service delivery.

• Differentiate Shield-specific cancellations from overall Guesty churn, and monitor coverage reductions among existing clients.

• Maintain ongoing relationships with insurers, claims administrators, and other program partners.

• Direct commercial discussions, renewals, performance reviews, and escalations, coordinating with Finance and Legal departments.

• Negotiate enhancements to commercial terms, service levels, and operational processes.

• Collaborate with Finance to track program revenue, margins, and operating costs, identifying opportunities to boost profitability while upholding service and coverage quality.

• Manage partner transitions effectively to ensure service continuity.

⛳️ Requirements

• Previous experience in the short-term rental (STR) or vacation rental sector, with a solid understanding of property manager operations, guest-related damages, and protection needs.

• Over 5 years of relevant experience in program management, insurance or protection programs, operations, or a closely related domain.

• Demonstrated experience in directly managing and developing an operational team.

• Experience in managing insurers or insurance partners, including commercial negotiations and service performance oversight.

• Strong grasp of claims workflows, customer service, and operational controls.

• Commercial and analytical acumen, with the capability to leverage data for improving retention, profitability, and service quality.

• A history of leading cross-functional initiatives from inception through execution.

• Excellent communication, negotiation, and problem-solving abilities.

• Capacity to work across diverse markets and time zones while taking ownership in a fast-paced environment.

• Familiarity with embedded insurance or property protection programs (preferred).

• Experience managing international programs and partner relationships (preferred).

• Background in implementing workflow automation, operational dashboards, or claims management systems (preferred).

🏝️ Benefits

• Equal employment opportunities regardless of race, color, religion, sex, age, national origin, disability, veteran status, pregnancy, sexual orientation, or any other characteristic protected by law.