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Added 4 mins ago
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Customer Success Manager (AMER)
ApprovalMax
Toronto, ON
- Full-time
ApprovalMax is on the lookout for a motivated Customer Success Manager to join its dedicated Toronto team. In this role, you will act as a trusted advisor to our customers, helping them…
Added 4 mins ago
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Retail Sales Associates- Lime Ridge
Lovisa
Hamilton, ON
- Part-time
We're seeking an energetic and customer-focused Sales Associate to join our retail team. The ideal candidate will provide exceptional customer service while supporting store operations and…
Added 4 mins ago
JI
Paid Media Specialist
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- Full-time
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Added 4 mins ago
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Retail Store Manager - Stone Road
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Guelph, ON
- Full-time
We're seeking a dynamic and results-driven Retail Store Manager to lead our store operations and drive business growth.
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Manager, Cybersecurity
KPMG
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- Full-time
Our Calgary team is looking for highly motivated Cyber Security professionals at the Manager level to join our team! As a member of KPMG Canada’s cross-functional Cyber team, you will be…
Added 20 mins ago
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Lumber Sales Associate Part-Time - 7180 Winnipeg North
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- Part-time
Sales Associates provide fast, friendly service by actively seeking out customers to assess their needs and provide assistance. Sales Associates have an emphasis on department and product…
Added 34 mins ago
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Added 34 mins ago
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Finance and Administrative Coordinator
The University of British Columbia
Vancouver, BC
- $4,719 to $4,960 CAD / month
- Full-time
The purpose of the Finance and Administrative Coordinator is to provide support for for core internal College activities such as financial processing and membership processes. They process,…
Added 34 mins ago
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Senior Wealth Associate
National Bank of Canada
Medicine Hat, AB
- Full-time
…You will work closely with investment advisors, a portfolio manager and other professionals, playing an important role in client service, financial planning, business development and the…
Added 34 mins ago
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Senior Wealth Associate
National Bank of Canada
Toronto, ON
- Full-time
…work closely with investment advisors to ensure exceptional customer service and smooth branch…
Added 34 mins ago
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Senior Analyst - SSI Expert
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Montreal, QC
- Full-time
Support business partners by resolving complex operational issues and delivering professional, efficient, and solution-oriented service.
Added 34 mins ago
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BANKING ADVISOR
National Bank of Canada
Sainte-Thérèse, QC
- Full-time
Support your clients through the mortgage renewal or renegotiation process.
Added 34 mins ago
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Wealth Associate
National Bank of Canada
Winnipeg, MB
- Full-time
Support wealth advisors in providing superior client service and be available to respond to client requests in a timely and professional manner.
Added 34 mins ago
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Wealth Associate
National Bank of Canada
Calgary, AB
- Full-time
Support investment advisors in providing superior customer service and be available to meet client requests
Added 34 mins ago
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Wealth Associate
National Bank of Canada
Calgary, AB
- Full-time
…will help wealth advisors to stand out by offering exceptional customer service that will have a positive, long-term impact on our…
Added 1 hour ago
AH
Administrative Support III
Alberta Health Services
Wetaskiwin, AB
- Part-time
…working opportunity. Reporting to the CAS Area Coordinator/Manager, this position supports community health programs (Home Care, Allied Health) operating at the Community Health Centre by:…
Added 1 hour ago
TH
Lumber Sales Associate Part-Time - 7255 Cranbrook
The Home Depot Canada
Cranbrook, BC
- Part-time
Sales associates provide fast, friendly service by actively seeking out customers to assess their needs and provide assistance. Sales associates have an emphasis on department and product…
Added 1 hour ago
GE
Little Chief Restaurant Evening Server
Grey Eagle Resort & Casino
Calgary, AB
- Full-time
Under the direction of the Hotel Food & Beverage Manager or Shift Supervisor, the Server is responsible for adhering to all policies and procedures within the Hotel and for making each…
Added 1 hour ago
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Hospitality F&B Assistant Manager
Grey Eagle Resort & Casino
Calgary, AB
- Full-time
…Restaurant” as an Indigenous experience for our customers through a ‘customer comes first’ attitude by providing hands-on, timely quality service, exceptional value, and a superior…
Added 1 hour ago
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Program Specialist
Niagara Region
ON · Niagara, ON
- Full-time
…recognizes the value of having flexible work arrangements to support better work-life balance for our employees. Hybrid work arrangements may vary from one employee to another and may also…
Added 1 hour ago
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Bilingual Customer Success Manager (French/English-Speaking)
Salesforce Partner Canada
Montreal, QC
- Full-time
The Customer Success Manager (CSM) is a versatile expert responsible for ensuring high-value customers who purchase the Signature Success Plan achieve a significant return on their…
Added 1 hour ago
BV
CUSTOMER SERVICE ASSISTANT
Bureau Veritas | Marine & Offshore
AB · Edmonton, AB
- Full-time
Team Development: Train new staff, participate in cross-training, and support overall Customer Service team success
Added 1 hour ago
AH
Supervisor
Alberta Health Services
AB · Greater Edmonton Metropolitan Area
- Full-time
…committed to providing nutritious, healthy, high-quality meal service to patients, staff, visitors, and the community. This Regular Full-Time position will work within a supervisory team to…
Added 1 hour ago
PM
Project Manager
POD Marketing
Calgary, AB
- $57,000 to $65,000 CAD / year
- Full-time
As our Project Manager, you’ll lead website projects from initial planning through launch, helping turn client goals into websites that support their business. Reporting to the Team Lead of…
Added 1 hour ago
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Care & Support Representative (Temporary Contract)
Engaged
Remote, Canada
- $18 to $23 CAD / hour
- Full-time
- Remote
Uphold the highest level of Customer Service by being flexible, attentive, reliable and responsive with our clients and colleagues

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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