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Added 12 mins ago
BT
Audit and Assurance Manager
Baker Tilly Canada
Cobourg, ON
- Full-time
We are looking for an Audit and Assurance Manager to join our team - a role where your expertise will drive meaningful outcomes and your ambition will help shape what comes next. Here,…
Added 12 mins ago
BR
Senior Manager, Accounting
Brookfield Renewable
Gatineau, QC
- Full-time
Reporting directly to the Director, Accounting, the Senior Manager, Accounting will provide hands-on leadership to accounting teams and act as a critical bridge between strategy and…
Added 12 mins ago
KG
Manager - Health and Safety Risk and Assurance
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Toronto, ON
- Full-time
Dress Code: Business Casual A Great Place to Work
Added 12 mins ago
Sales Associate, Sales & Partnerships - Scotia iTRADE (Cantonese)
Scotiabank
Toronto, ON
…the adequacy, adherence to and effectiveness of day-to-day business controls to meet obligations with respect to operational, compliance, AML/ATF/sanctions and conduct…
Added 12 mins ago
Senior Manager, Data Product Management
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Toronto, ON
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Added 12 mins ago
OEM Client Relationship Manager
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The OEM Client Relationship Manager is an automotive industry specialist in Dealer Finance who serves as a dedicated point of contact for a selected Original Equipment Manufacturer (OEM)…
Added 12 mins ago
A
Co-Op Student - Project Support (DA)
AltaLink
Calgary, AB
- Other
A Co-Op Student position is available in the Project Support team. The team includes project controls analysts (PCA), project accountant administrators (PAA), capital reporting analysts and…
Added 12 mins ago
Resource Governance Advisor
Government of Alberta
AB
The ESO branch is looking for two (2) Resource Governance Advisors. Reporting to the Manager, Project Standards and Controls, this position is responsible for leading the effective…
Added 27 mins ago
VC
Project Manager (Substation Construction)
Valard Construction
Calgary, AB
- Full-time
Our Substation group is currently looking to add a Project Manager to our team, based in Calgary, AB.
Added 27 mins ago
OT
Restaurant Manager
One Therapy Network
Victoria, BC
- Full-time
The Restaurant Manager is responsible for all aspects of restaurant operations including the quality and consistency of the customer experience, adherence to A&W standards, Provincial WCB,…
Added 28 mins ago
TI
General Sales Manager - Ottawa
Trane Italia
Ottawa, ON
- Full-time
Trane is looking for a dynamic and compassionate General Sales Manager for our Ottawa, ON office, committed to delivering business results and continually fostering employee engagement. You…
Added 28 mins ago
H
Assistant Manager - Food and Beverage
Hilton
Mississauga, ON
- Full-time
As an Assistant Food & Beverage Manager, you will help lead outlet operations while supporting banquet operations when needed. You will assist with daily service execution, Team Member…
Added 43 mins ago
WS
Manager IT Service Management (ITSM)
Workplace Safety and Insurance Board (WSIB)
London, ON
- Full-time
…continue to modernize our IT environment, we’re looking for a Manager, IT Service Management (ITSM) to help strengthen how reliable, effective and customer-focused technology services are…
Added 43 mins ago
Slot Technician Supervisor- Casino Brantford
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Brantford, ON
Under the general direction of the Manager, Operations, this position is responsible for the leadership and coordination all Slot Technician activities. The Slot Technician Supervisor…
Added 43 mins ago
MM
Global Financial Crime Screening Operations Manager
Marsh McLennan
Toronto, ON
- Full-time
…governance frameworks, working on projects to enhance screening controls and processes in conjunction with global business, Compliance and IT operations stakeholders. The role holder should…
Added 43 mins ago
Payroll Manager
Imperial Brady
Montreal, QC · Saint-Laurent, QC
The Payroll Manager is responsible for the leadership, administration, accuracy, and compliance of all payroll operations across Canada. This role oversees the day-to-day payroll function…
Added 43 mins ago
General Manager, Ontario
F12.net
Markham, ON
The Position: Reporting to the COO, the General Manager (GM) is responsible for F12’s financial and operational performance at the provincial or regional level with a focus on driving…
Added 43 mins ago
Payroll Manager, North America
Superior Plus Propane Talent Acquisition
Cambridge, ON
The Payroll Manager is responsible for leading and managing payroll operations across the United States and Canada. This role ensures accurate and timely payroll processing, compliance with…
Added 43 mins ago
HF
Automation Systems Operator
Hilton Food Group Plc
Brantford, ON
- $21.63 to $27 CAD / hour
…a 24/7 mission-critical environment. This role monitors and controls automation platforms, responds to system incidents and alarms, coordinates with cross-functional teams, and supports…
Added 43 mins ago
Warehouse Automation Specialist
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Brantford, ON
This role is at the heart of driving our business capability and building a fantastic environment for all our colleagues.
Added 43 mins ago
O
Manager, Corporate Reporting and Financial Services
OPTrust
Toronto, ON
- Full-time
…roles supporting OPTrust investment and pension activities. The Manager, Corporate Reporting and Financial Services supports accurate, timely, and compliant reporting for the Fund and…
Added 43 mins ago
B
Business Intelligence Specialist
Bevertec
Toronto, ON
- Contract
This is a hands-on role responsible for ensuring the stability, security, performance, and availability of a business-critical data platform that supports analytics, reporting, data…
Added 43 mins ago
A
Co-Op Student - Project Support (DA)
AltaLink
Calgary, AB
- Internship
A Co-Op Student position is available in the Project Support team. The team includes project controls analysts (PCA), project accountant administrators (PAA), capital reporting analysts and…
Added 43 mins ago
NP
Director, Internal Controls & Finance Transformation
Neo Performance Materials
Toronto, ON
- $140,000 to $170,000 CAD / year
- Full-time
Neo is seeking a Director to strengthen how we manage internal controls, policies and continuous improvement across its global business. This role combines ownership of the finance policy…
Added 58 mins ago
T
Treasury Analyst, Liquidity Measurement - Analytics & Reporting
TD
Toronto, ON
- Full-time
$69,700 - $98,400 CADThis role is eligible for a discretionary variable compensation award that considers business and individual performance.

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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