Shield Program Lead

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

📋 Description

• Oversee the daily operations of Shield in all active markets, ensuring clear processes, accountability, and consistent service delivery.

• Develop reporting mechanisms, controls, and escalation procedures while addressing recurring operational challenges.

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

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

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

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

• Set and monitor service levels to ensure prompt customer communication and payment.

• Resolve overdue claims and complex escalations, holding partners accountable for their commitments.

• Ensure claims are processed accurately and consistently in line with applicable coverage terms.

• Take ownership of Shield's retention performance and spearhead initiatives aimed at reducing churn in collaboration with Customer Success.

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

• Address retention challenges associated with pricing, coverage, claims experience, and service delivery.

• Differentiate Shield-specific cancellations from broader Guesty churn and monitor declines in coverage among existing clients.

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

• Lead commercial negotiations, renewals, performance evaluations, and escalations, working closely 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 enhance profitability while ensuring service and coverage quality.

• Manage partner transitions to guarantee 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 damage, and protection needs.

• A minimum of 5 years of relevant experience in program management, insurance or protection programs, operations, or a closely related field.

• 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 to enhance retention, profitability, and service quality.

• Proven track record of leading cross-functional initiatives from planning to execution.

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

• Ability to navigate across markets and time zones while taking ownership in a dynamic environment.

• Experience in embedded insurance or property protection programs is preferred.

• Experience managing international programs and partner relationships is preferred.

• Familiarity with implementing workflow automation, operational dashboards, or claims management systems is preferred.

🏝️ Benefits

• Remote position.

• 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.