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Added 14 mins ago
EG
Business Development Manager - Power Transmission
EMAGE Group
Canada
- Full-time
Relevant experience in positions such as Project Manager, Project Director, Business Development Manager, BD Director, Commercial Director, or Business Director.
Added 15 mins ago
AH
Senior Project Manager
Alberta Health Services
AB · Greater Edmonton Metropolitan Area
- Temporary
The Senior Project Manager provides expertise, leadership and oversight on assigned capital and operating building infrastructure projects at healthcare sites and is responsible for all…
Added 15 mins ago
QR
Sales Representative - Industrial
Quincaillerie Richelieu
Mississauga, ON
- Full-time
Under the supervision of the Industrial Sales Manager, the Sales Representative will be responsible for all sales activities and management of customer accounts within a set territory. The…
Added 1 hour ago
KG
Multifamily Property Accountant (Toronto)
Kipling Group
Toronto, ON
- Full-time
…management companies. Our core focus is property management – both commercial and residential. With offices in Toronto, Kitchener-Waterloo, Calgary and Edmonton, Kipling currently manages…
Added 2 hours ago
Senior Consultant / Manager, Financial Advisory
Teneo
Toronto, ON
As a Senior Consultant / Manager you will have the opportunity to use your commercial awareness and professional expertise, along with leveraging the skills and expertise of others, to…
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RB
Financing Specialist
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- Full-time
As a skilled financing specialist supporting a high performing commercial banking team with portfolio management and compliance support you will contribute to an exceptional client…
Added 2 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 2 hours ago
Manager, Advisory Services
Affinity Credit Union
Watrous, SK
Lead a team of advisors as a Manager of Advisory Services at our Watrous, Strasbourg, Nokomis, & Colonsay locations. You’ll coach talent that delivers exceptional service & professional…
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MM
Customer Success Manager - Measure Marketing
Measure Marketing Results Inc.
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- Full-time
- Remote
B2B, law firms, signage, SaaS, and residential and commercial home improvement
Added 2 hours ago
DW
Intermediate Structural Engineer (P.Eng.)
Design Works Engineering
Grande Prairie, AB
- Full-time
Multi-family residential, commercial and institutional buildings across Alberta and Canada
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Intermediate Structural Engineer (P.Eng.)
Design Works Engineering
Calgary, AB
- Full-time
Multi-family residential, commercial and institutional buildings across Alberta and Canada
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Intermediate Mechanical Engineer (P.Eng.)
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Commercial, institutional, low- and high-rise, and multi-family residential buildings across Alberta and Canada
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Intermediate Mechanical Engineer (P.Eng.)
Design Works Engineering
Edmonton, AB
- Full-time
Commercial, institutional, low- and high-rise, and multi-family residential buildings across Alberta and Canada
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DW
Intermediate Mechanical Engineer (P.Eng.)
Design Works Engineering
Calgary, AB
- Full-time
Commercial, institutional, low- and high-rise, and multi-family residential buildings across Alberta and Canada
Added 3 hours ago
TS
Electrical Engineer Lead
TalentSphere Staffing Solutions
ON · Ontario, Canada
- Full-time
Related Titles: Electrical Engineer, Project Manager (Electrical), Electrical Designer, Building Systems Engineer
Added 3 hours ago
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Building Envelope/Restoration Project Manager
TalentSphere Staffing Solutions
Calgary, AB
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Project Manager – Building Envelope/Restoration
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Senior Contract Administrator
Morson Edge (Canada)
Toronto, ON
- $60 to $75 CAD / hour
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Escalates complex, high-profile issues/matters to the Commercial Manager.
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Private Banker
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…Management Advisor/Counsellor for long-term investment advice, or a Commercial Account Manager for a business…
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Relationship Manager, Business Market
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Completion of the Associate Account Manager training program, or have previous experience as a small business owner, or in similar field
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Recoveries Officer
Royal Bank of Canada
Mississauga, ON
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RBC is committed to supporting flexible work arrangements when and where available. Details to be discussed with Hiring Manager.
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Engineering Manager Structural Bridge
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L'Oréal
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…Canadian portfolio, driving go-to-market execution and sustained commercial performance alongside Sales, Supply Chain, and Digital…
Added 3 hours ago
TS
Regional Manager - Edmonton
TalentSphere Staffing Solutions
AB · Edmonton, AB
- Full-time
We are seeking an experienced Regional Manager to lead business growth, operational performance, and client relationships within a growing commercial construction environment.
Added 3 hours ago
TS
Project Manager
TalentSphere Staffing Solutions
Mississauga, ON
- Full-time
Our client has projects all over the GTA and have built very strong relationships with major Commercial clients. We are looking for a Project Manager to own the process for these clients…
Added 3 hours ago
TS
Project Manager
TalentSphere Staffing Solutions
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Grow your Construction career as a Project Manager with an established General Contractor in the Commercial Construction, Design/Build arena! With a focus on Light Industrial Buildings,…

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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