Shield Program Lead

Guesty

. Own the day-to-day operation of Shield across all active markets, with clear processes, accountability and consistent service delivery .

Posted 11/1/2026full-timeRemote • CanadaSeniorWebsite

Core Competencies

Role fit

Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates expertise in program management and operational leadership within the short-term rental industry, focusing on claims management, customer service, and process improvement. Proven ability to negotiate with insurers and manage partner relationships while driving retention and profitability.

Highest-signal resume keywords

Program ManagementClaims Workflow ManagementOperational ControlsNegotiation SkillsCross-Functional Leadership

ATS Keywords

Tailor your resume

Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills

Claims ManagementOperational ImprovementData AnalysisPerformance ManagementProcess Automation

Soft Skills

Strong CommunicationProblem-SolvingCoachingAccountability

Tools & Technologies

Claims Management SystemsOperational Dashboards

Industry Keywords

Short-Term RentalVacation RentalInsurance ProgramsProperty ProtectionCustomer Retention

About the role

Key responsibilities & impact

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
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
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
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

Requirements

What you’ll need

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

Benefits

Comp & perks

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