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Route Service Supervisor - UniFirst Canada
UniFirst
Kingston, ON
- Full-time
At UniFirst, we Always Deliver - for our customers and our people. As a Route Service Supervisor you’ll lead and work alongside a team of Route Service Representatives who service a diverse…
Added 1 min ago
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Maintenance Manager
BGO Real Estate
Cambridge, ON
- Full-time
The Maintenance Manager is responsible for the effective delivery of maintenance and building operations within an assigned residential property or portfolio. The role ensures building…
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Design Engineer
RJC Engineers
Ottawa, ON
- Full-time
Lead with Purpose – You empower, support, and guide others, driving meaningful results.
Added 1 min ago
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Chairman's Club Supervisor, Rogers Place
Compass Canada
Edmonton, AB
- Part-time
Welcome guests in a professional and friendly manner and ensure delivery of consistently outstanding service by all associates
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Hospitality Manager - Retail
MAPLE LEAF LOUNGE
Toronto, ON
- Full-time
Lead all day-to-day unit operations, ensuring exceptional service delivery, operational excellence, and compliance with client and Compass standards.
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Technical Program Manager, Platform Services
Motive
Vancouver, BC
Lead end-to-end execution of complex, cross-functional technical programs across Platform Services Engineering, from definition and planning through delivery and adoption.
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Senior Revenue Enablement Specialist, Digital
Quadient
Markham, ON
- $90,000 to $100,000 CAD / year
- Full-time
…skills and make a real impact – help our future-focused business lead the way in powering secure and sustainable business connections through digital and physical…
Added 15 mins ago
Delivery Manager – Personalization and Marketing (7 months contract)
Sobeys Capital Incorporated or a Franchise/Affiliate / ou une franchise/société affiliée
Toronto, ON
As a Delivery Manager in Personalization and Marketing, you will lead the end-to-end delivery of multiple Advanced Analytics and AI/ML initiatives, overseeing planning, execution,…
Added 15 mins ago
Grocery - Manager Grocery
Sobeys Capital Incorporated or a Franchise/Affiliate / ou une franchise/société affiliée
Ottawa, ON
What began as a meat delivery business in Stellarton, Nova Scotia has grown to over 128,000 teammates at corporate-owned and franchised/affiliate store locations. Sobeys Capital…
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Coordonnateur des opérations - Operations Coordinator
Ice River Sustainable Solutions
Lachute, QC
Added 15 mins ago
Corporate Store Supervisor I
Bulk Barn
St. Albert, AB
Facilitate and assist with placing Warehouse and Direct Store Delivery (DSD) orders.
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Director, Individual Portfolio Management
Equitable
Waterloo, ON
…program oversight, and people leadership, driving the successful delivery of key initiatives and business value across the…
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TPSS Work Package Manager
Trillium Rail Partners
Mississauga, ON
- Full-time
TRP has a current vacancy for an OCS-TPSS Work Package Manager that will be responsible for the full lifecycle delivery of the Traction Power Supply System (TPSS) across the ECWE project.…
Added 16 mins ago
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Technology Lead Enterprise Platforms and Operations
Tundra Technical Solutions
Toronto, ON
- $140,000 to $145,000 CAD / year
- Full-time
As the Technology Lead, Enterprise Platforms and Operations, you will drive a holistic strategy to modernize our digital workplace, transforming disconnected processes and siloed…
Added 16 mins ago
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Director Of Sales
The Erb Group
Vaudreuil-Dorion, QC
- Full-time
The Erb Group is seeking a Director of Sales for Quebec and Eastern Canada. In this role, you will lead and coach the regional sales team, strengthen accountability, grow revenue across…
Added 16 mins ago
RD
Technical Project Manager
Randstad Digital
Toronto, ON · Greater Toronto Area, Canada
- Full-time
We are seeking an adaptable, results-oriented Project Manager to lead and support high-impact, multi-year enterprise automation initiatives. In this role, you will bridge the gap between…
Added 16 mins ago
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Scrum Master
Procom
Toronto, ON
- Contract
Lead execution of initiatives using adopted methodologies; assess and adapt for quality delivery.
Added 16 mins ago
QT
Building Science Lead
QEA Tech
Toronto, ON · Greater Toronto Area, Canada
- Full-time
The Building Science Lead will be responsible for maintaining the quality and consistency of technical deliverables, supporting the development of team members, helping coordinate…
Added 16 mins ago
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Manager, Data Integration
Prophix
Toronto, ON · Etobicoke, ON
- Full-time
Lead delivery of ETL solutions that connect customer source systems to Prophix, covering data imports, data transformations, and data modeling end-to-end
Added 16 mins ago
PC
Project Manager
Peters Construction Group
ON · Niagara, ON
- Full-time
We are seeking an experienced and results-driven Project Manager to lead the successful delivery of complex civil construction projects within the sewer and watermain sector. This role is…
Added 16 mins ago
OC
Implementation Consultant, Ivalua
Optis Consulting
Calgary, AB
- Full-time
…Toronto, Calgary, Montreal, or New York teams. Our Consultants lead the development of solutions by interviewing key stakeholders, gathering, and organizing information, analyzing data,…
Added 16 mins ago
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Lead, Forward Deployed Engineering
Deliverect
Toronto, ON
- Full-time
…evolving digital landscape, streamlining digital ordering for delivery and on-premise services. We are committed to creating user-friendly, dependable, and scalable technology that…
Added 16 mins ago
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Lead, Management Operating System (MOS) Design
Brunel
Vancouver, BC
- $122,000 to $150,000 CAD / year
- Full-time
Brunel is seeking an experienced Lead, Management Operating System (MOS) Design to support the design, development, documentation and continuous improvement of a Management Operating System…
Added 16 mins ago
SS
Head of Manufacturing
SkyCan Systems
Barrie, ON
- Full-time
THE ROLE This role owns SkyCan's entire manufacturing organization, from design release through delivery and sustainment. It is a ground-level operational build. You will stand up SkyCan's…
Added 30 mins ago
BG
Vice President, Business Operations
Brandt Group of Companies
Regina, SK
- Full-time
Lead the development and execution of the Clubs’ annual business plans, aligning departmental goals with organizational objectives and long-term strategy.

Guesty

Shield Program Lead

Canada

Full-time

Apply About employer

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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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