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Added 27 mins ago
M
Program Manager, Investigation Services
Manulife
Halifax, NS · Kitchener, ON · Toronto, ON · Waterloo, ON · Montreal, QC
- Full-time
We are looking for someone who brings a strong foundation in insurance investigations and can help strengthen investigative thinking, practices, and capabilities across the team. Previous…
Added 27 mins ago
MD
Compliance Supervisor/Workers' Compensation Program Supervisor
Minnesota Direct Care and Treatment
Saint-Paul, NB · St.-Paul, NB
- Full-time
…(CRT). The compliance team monitors all workers’ compensation claims filed with DLI to ensure the timely and accurate delivery of benefits to injured workers, including auditing and the…
Added 27 mins ago
NC
Client Assistant, Commercial Insurance
NFP Corp
Grande Prairie, AB
- Full-time
…in our offices, on a call, out in the field or anywhere you can find us in the world, we’re starting the conversations that create a more secure future for…
Added 28 mins ago
KH
Accounts Payable Specialist
Kids Help Phone
Toronto, ON
- $50,000 to $57,000 CAD / year
- Full-time
Are you motivated by the chance to help ensure all young people in Canada can access mental health support and Feel Out Loud? Kids Help Phone (KHP) is Canada’s Unlock The Hope Youth…
Added 1 hour ago
G
Insurance Advisor, Sales & Service
Gallagher
Toronto, ON
- Full-time
…Year 2025, Proptech30 2025, Insurance Business Canada’s 5-Star Claims 2024, Insurance Business Canada’s Top Insurance Employer 2022 & 2021 and Digital Innovator of the Year 2022,…
Added 1 hour ago
T
TD Insurance, Legal Assistant III
TD
Saint John, NB
- Full-time
As a candidate, you are encouraged to ask compensation related questions and have an open dialogue with your recruiter who can provide you more specific details for this role.
Added 2 hours ago
FD
Logistics Account Executive, Freight & Carrier Sales
Fil Delivery
Mississauga, ON
- Full-time
…team - so Account Managers and Business Development Managers can spend their time winning business instead of managing operational fires. It doesn't carry a revenue book, but it carries…
Added 3 hours ago
A
Future Opportunities: SR&ED Consultant
Ayming
Toronto, ON
- Full-time
Planning, organizing and executing SR&ED claims, including interviews of technical personnel, and structuring projects according to government criteria
Added 7 hours ago
G
Shield Program Lead
Guesty
Canada
- Full-time
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…
Added 9 hours ago
TS
Development Coordinator
TalentSphere Staffing Solutions
Toronto, ON
- Full-time
Responsible for day-to-day departmental administrative tasks, including processing expense claims and file maintenance.
Added 9 hours ago
TS
Project Manager
TalentSphere Staffing Solutions
AB · Edmonton, AB
- Full-time
Prepare monthly progress claims and submit to the Owner for payment
Added 10 hours ago
HT
Test Engineering Technologist
Husky Technologies
Bolton, ON
- Full-time
…understanding of the developmental engineering process. This role can therefore also be a great foundation for future…
Added 11 hours ago
TO
Senior Advisor, WSIB & Return To Work
The Ottawa Hospital
Ottawa, ON
- Full-time
Added 11 hours ago
T
General Counsel
Techo-Bloc
Longueuil, QC · Saint-Hubert, Quebec
- Full-time
Review active legal files, disputes, warranty claims, insurance, employment, and other open matters; prioritize issues, make recommendations, and establish a clear handoff process.
Added 11 hours ago
AC
Senior Actuarial Analyst, Personal Pricing
Aviva Canada
Markham, ON
- Full-time
Collaborate with Product, Underwriting, Distribution, Claims, and Business Development partners on pricing and broker initiatives.
Added 11 hours ago
L
Executive Assistant II
lululemon
Vancouver, BC
- Full-time
…department expenses, including the review of employee expense claims for accuracy and adherence to policy on behalf of…
Added 12 hours ago
HT
Test Engineering Technologist
Husky Technologies
Bolton, ON
- Full-time
…understanding of the developmental engineering process. This role can therefore also be a great foundation for future…
Added 12 hours ago
WC
(CAN) Consumables Associate
Walmart Canada
Markham, ON
- Full-time
Ensures proper handling of claims and returns, secures merchandise, identifies high shrink items and maintains a safe work environment as per Company policies and procedures.
Added 12 hours ago
WC
(CAN) Consumables Associate
Walmart Canada
North Sydney, NS
- Full-time
Ensures proper handling of claims and returns, secures merchandise, identifies high shrink items and maintains a safe work environment as per Company policies and procedures.
Added 12 hours ago
LH
Manager, Legal Services and General Counsel
London Health Sciences Centre (LHSC)
London, ON
- Full-time
…offering expert legal counsel and representation on complex claims, litigation risks, regulatory matters, and high-risk patient issues. The Manager will also lead comprehensive legal…
Added 12 hours ago
SC
Personal Lines Senior Underwriter
SPG Canada
Vancouver, BC
- Full-time
…value to our partners is further enhanced through our in-house claims management team, Specialty Claims…
Added 13 hours ago
S
Consultant (CAN) - Inventory and Procurement Specialist
Slalom
Toronto, ON · Greater Toronto Area, Canada
- Full-time
…purpose, flexibility, connection, and recognition, so our people can thrive and love what they do, most…
Added 13 hours ago
MS
Personal Injury Law Clerk
Minted Search Group
Toronto, ON · Greater Toronto Area, Canada
- Full-time
…opportunity for a clerk who understands the full lifecycle of a file, can move matters forward proactively, and enjoys taking meaningful ownership of sophisticated client…
Added 13 hours ago
CI
Litigation Associate Lawyer – Class Action & Insurance Litigation
Cartel Inc.
Toronto, ON · North York, ON
- Full-time
…insurance litigation files, including Motor Vehicle Accident (MVA) claims, this role offers the unique chance to work on class action cases retained on behalf of a government…
Added 13 hours ago
WI
Renewal Retention Specialist
Westland Insurance Group Ltd.
Regina, SK · Greater Regina Metropolitan Area
- Full-time
Westland is committed to continuous learning where employees can grow their potential and write the stories of their careers. Financial assistance is available for approved work-related…

Guesty

Shield Program Lead

Canada

Full-time

Apply About employer

Applications open in a new tab.

Job details

Job type: Full-time
Experience: 5+ years of relevant experience in program management, insurance or protection programs, operations, or a closely related field.
Posting language: English
Posted: Oct 30, 2026

Original job description

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.

Responsibilities

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.

Requirements

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.

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.

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.

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More about this job

Responsibilities

The Shield Program Lead will own the end-to-end operations, performance, and commercial relationships for the Guesty Shield program globally. This role involves managing the internal claims team, driving program profitability, and implementing process improvements to ensure high-quality service delivery.

Requirements

Candidates must have at least 5 years of experience in program management, insurance, or operations, with specific expertise in the short-term rental industry. Proven ability to lead operational teams, manage commercial partnerships, and utilize data for decision-making is essential.

Skills

Program Management
Insurance Operations
Claims Management
Team Leadership
Commercial Negotiation
Customer Retention
Short-term Rental Industry
Operational Efficiency
Data Analysis
Process Improvement
Stakeholder Management
Risk Management
Workflow Automation
Performance Management
Strategic Planning

Visa sponsorship

Not detected in the job text

Keywords

Guesty Shield
Short-term Rental
Vacation Rental
Insurance
Claims Processing
Program Management
Operational Controls
Customer Success
Churn Reduction
Commercial Partnerships
Profitability Analysis
Automation
Service Level Agreements
Property Management
Risk Mitigation
Cross-functional Leadership
Hospitality Technology
Embedded Insurance
Performance Metrics
Quality Assurance

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