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Added 1 min ago
RH
Product Program Manager
Robert Half
Toronto, ON · Greater Toronto Area, Canada
- $100,000 to $110,000 CAD / year
- Full-time
Drive cross-functional delivery across membership, finance, and operations teams
Added 1 min ago
S
CRM Analyst
Sagard
Toronto, ON · Montreal, QC
- Full-time
Reporting to the Senior Manager CRM Strategy, this role will execute against the DealCloud roadmap and vision, translating requirements into configured outcomes, clean data and reliable…
Added 30 mins ago
LD
Program Manager- Supply Chain
Leonardo DRS
Bedford, QC
- Full-time
The Supply Chain Program Manager (SCPM) is responsible for leading supply chain execution for assigned programs and serving as the primary liaison between Supply Chain and Program…
Added 30 mins ago
S
Desktop Support Analyst
Stantec
Saskatoon, SK
- Full-time
…Functional Services Teams (FSTs) include Corporate Development, Finance, Human Resources, HSSE, IT, Legal, Marketing/Communications, Practice Services, and Real Estate and Procurement. By…
Added 1 hour ago
FR
Accounts Payable Associate
FirstService Residential Canada
Vancouver, BC
- Full-time
Ensure cheques are delivered according to the delivery instructions and coordinate couriers and pick-ups as required
Added 1 hour ago
PC
Financial Advice Manager
Provincial Credit Union
Charlottetown, PE
- Full-time
The Financial Advice Manager strengthens the delivery of consistent, high-quality financial advice across Provincial Credit Union. This role leads the onboarding, training and ongoing…
Added 1 hour ago
RM
Manager
Ross Memorial Hospital
Kawartha Lakes, ON · Lindsay, ON
- Full-time
The Unit Manager reports to the Director of Medicine, ICU, Respiratory and Post Acute Care. They promote, facilitate, and manage the unit environment in such a way that patients receive…
Added 1 hour ago
DA
Customer Sales Representative (No Auto Experience Required)
Davis Auto Group
Okotoks, AB
- Full-time
Work closely with the Sales Manager and Finance Manager to arrange for vehicle financing, applications and warranty
Added 1 hour ago
KC
Fleet Specialist
Kia Canada
Mississauga, ON
- Full-time
The role of the Fleet Specialist will be to provide support to both the Fleet Manager and Supervisor. The Specialist will report directly to the Fleet Supervisor. The incumbent will…
Added 2 hours ago
VA
Manager, Compensation and Benefits
Vancouver Airport Authority
Vancouver, BC
- Full-time
We have an opportunity for a permanent, full-time Manager, Compensation & Benefits on the People & Culture team. Reporting to the Director, People Operations, the Manager leads YVR’s…
Added 2 hours ago
JI
Paid Media Specialist
Jumbo Interactive
Calgary, AB
- Full-time
For more than 30 years, Stride has brought together the strategy, marketing, technology, customer service, finance, operations, regulatory expertise, and project management required to…
Added 3 hours ago
S
Healthcare IT Project Manager
Sectra
Vancouver, BC
- Full-time
…progress tracking, cross-functional collaboration, and timely…
Added 4 hours ago
KG
Property Manager (Oakville)
Kipling Group
Toronto, ON
- Full-time
Liaise with accounting team to ensure accuracy and timely delivery of all client reports.
Added 4 hours ago
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Shield Program Lead
Guesty
Canada
- Full-time
Own the day-to-day operation of Shield across all active markets, with clear processes, accountability and consistent service delivery.
Added 6 hours ago
ME
Senior Contract Administrator
Morson Edge (Canada)
Toronto, ON
- $60 to $75 CAD / hour
- Contract
Identify and advise on the resolution of a range of critical contract issues with the project delivery teams and vendors to resolve contractual inconsistencies, irregularities, and other…
Added 6 hours ago
RD
Technical Project Manager - AI
Randstad Digital
Montreal, QC · Greater Montreal Metropolitan Area
- $70 to $90 CAD / hour
- Contract
A top-tier financial institution is seeking an accomplished Senior Technical Project Manager to orchestrate high-impact technology initiatives across enterprise data platforms, financial…
Added 6 hours ago
RB
Relationship Manager, Business Market
Royal Bank of Canada
Ottawa, ON
- Full-time
Acquire, grow and deepen client relationships through delivery of value-added, tailored financial advice to meet their needs
Added 6 hours ago
CC
Manager – Acute Care/Emergency
Canadian College of Health Leaders - Northwestern Ontario Chapter
Rocky Mountain House, AB
- Full-time
The Manager – Acute Care/Emergency is responsible for key decisions and maintaining standards; ensuring a focus on consistency in the delivery of patient & family centered care and…
Added 6 hours ago
AI
Business Project Manager, financial field
Avanciers Inc.
Montreal, QC
- $90 to $100 CAD / hour
- Contract
Avanciers Incorporated is hiring a [Business Project Manager, financial field] for one of our clients.
Added 6 hours ago
J
Global Category Manager EMS - Business Line Analytical
Jobgether
Canada
- Full-time
…global analytical business environment. As Global Category Manager, you will drive strategic procurement initiatives, optimize the supplier base, and strengthen supply chain resilience…
Added 6 hours ago
A
Project Manager
Affinity
Vancouver, BC
- Contract
The Project Manager will work closely with HR, Finance, Technology, business stakeholders, other Project Managers, and a certified Workday Services partner. This is a highly…
Added 6 hours ago
A
Program Manager
Affinity
Vancouver, BC
- Contract
…interdependent workstreams. Each workstream will have its own project delivery structure, while the Program Manager will maintain the integrated program plan, manage cross-stream…
Added 6 hours ago
C
Test Manager
Cognizant
Toronto, ON
- Full-time
Cognizant is seeking an experienced Test Manager to lead quality assurance activities for FNZ platform releases, configuration changes, migrations, and upgrade cycles. The ideal candidate…
Added 6 hours ago
AC
Data Analytics Manager
Amphenol Communications Solutions
Markham, ON
- Full-time
We are seeking a Data Analytics Manager to lead our Enterprise BI and Analytics Service team and deliver trusted, actionable analytics that meet customer and business needs. This role will…
Added 6 hours ago
RI
Associate Product Manager (Accounting)
Remarcable, Inc.
Remote, Canada
- $90,000 to $120,000 CAD / year
- Full-time
- Remote
…rapidly scaling business, we’re looking for an Associate Product Manager (APM) who is excited to dive deep into our core Procure-to-Pay and accounting…

Guesty

Shield Program Lead

Canada

Full-time

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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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