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Added 15 mins ago
T
Software Engineer II - Angular UI
TD
Toronto, ON
- Full-time
Actively seek and support continuous improvement and automation opportunities within the engineering practice
Added 15 mins ago
TA
Technical Program Manager (GenAI)
Tiger Analytics Inc.
Remote, Canada
- Full-time
- Remote
…analytics to embrace Generative AI, agentic AI, intelligent automation, and cloud-native data platforms. A global presence across North America, Latin America, Europe, and…
Added 15 mins ago
TA
Sr Manager/ Associate Director - HR Analytics
Tiger Analytics
Canada
- Full-time
…analytics to embrace Generative AI, agentic AI, intelligent automation, and cloud-native data platforms. A global presence across North America, Latin America, Europe, and…
Added 15 mins ago
TC
Datastage developer
Tata Consultancy Services
Toronto, ON
- $100,000 to $120,000 CAD / year
- Full-time
Expert in working with Data Stage Manager, Designer, Administrator, and Director.
Added 15 mins ago
P
Senior Revenue Operations Manager
Pepper
Canada
- Full-time
Find the leverage. Dig into the funnel, the data, and rep workflows to spot where a tool, automation, or better data would make the biggest difference, and make the case for what to build…
Added 30 mins ago
ZT
Senior Manager Technical Program Management
Zebra Technologies
Mississauga, ON · CAN - Mississauga, Canada
- Full-time
We are seeking a Senior Manager of Technical Program Manager (software and hardware) with proven functional leadership ability to develop a team of program managers operating across all…
Added 30 mins ago
H
Structural Section Manager
HDR
Richmond Hill, ON · Toronto, ON
- Full-time
HDR is seeking a Structural Section Manager to join our growing Building Engineering Services (BES) group in Toronto. In this key leadership position, you will guide our structural design…
Added 45 mins ago
ZT
Project Manager
Zensar Technologies
Toronto, ON
- Full-time
Zensar is looking for a Onsite Project Manager at Toronto, Canada - French-speaking candidates are preferred
Added 45 mins ago
Manager, Web Development and Digital Experience (1-Year - Maternity Leave Contract)
Blue Ant Media Inc.
Toronto, ON
Manager, Web Development and Digital Experience (1 Year – Maternity Leave Contract)
Added 1 hour ago
M
People Services AI Solutions & Configuration Lead
Manulife
Toronto, ON · Waterloo, ON
- Full-time
Evaluate emerging Workday AI capabilities and recommend opportunities to improve employee and manager experiences.
Added 1 hour ago
H
Structural Section Manager
HDR
Toronto, ON
- Full-time
HDR is seeking a Structural Section Manager to join our growing Building Engineering Services (BES) group in Toronto. In this key leadership position, you will guide our structural design…
Added 1 hour ago
SG
Electrical Engineer & Project Manager, BESS
Socomec Group
Brampton, ON
- Full-time
…customer system overarching electrical, electrochemical, and automation areas. This position will be also responsible for the Engineering To Order (ETO) projects managements from the order…
Added 1 hour ago
R&
Controller
Robertson & Company Ltd.
Markham, ON
- Full-time
Lead and develop a finance and accounting team of approximately 5 FTEs, including 3 Cost Accountants, 1 Accounting Manager, and 1 Financial Analyst.
Added 1 hour ago
P
Mortgage Agent
Pineapple
ON · Ontario, Canada
- Full-time
Pineapple Platform: Utilize our proprietary, all-in-one CRM and deal management system featuring AI-enabled workflow automation, real-time data reporting, and automated marketing drip…
Added 1 hour ago
RD
Senior Project Manager
Randstad Digital
Aurora, ON
- Contract
Job Title: Senior Project Manager – Enterprise Systems Implementation
Added 1 hour ago
IG
Datacenter Technician
Insight Global
Varennes, QC
- $26 to $29 CAD / hour
- Full-time
…able to execute small projects on your own, and work with your manager in planning and executing larger local projects. You act as the initial escalation point for junior technicians. You…
Added 1 hour ago
EG
Manager, IT Operations
Etraveli Group
Toronto, ON
- Full-time
Implement and maintain the endpoint security baseline with our Manager, Security: MDM enforcement, disk encryption, EDR, OS and application patching, and local admin control
Added 1 hour 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 2 hours ago
AI
QA Functional Tester- AEM, CMS
Astra-North Infoteck Inc. ~ Conquering today’s challenges, achieving tomorrow’s vision!
Kitchener, ON
- Full-time
We are seeking an experienced AEM Tester to support testing activities for Adobe Experience Manager (AEM) applications. The ideal candidate will be responsible for validating CMS…
Added 2 hours ago
V
IT Manager / Gestionnaire TI
Vention
Montreal, QC
- Full-time
Build process automation and design the company’s approach to internal AI deployment
Added 3 hours ago
HT
A/P Administrator
Husky Technologies
Bolton, ON
- Full-time
…on-site position. You will report to the Shared Services AP Manager and will work as part of a team in a fully automated, full-cycle accounts payable role. If you are a people-person who…
Added 3 hours ago
FC
District Sales Representative - Western Region (BC)
Festo Canada
Vancouver, BC
- Full-time
Our curiosity has made us a driving force in automation technology for decades. Today, we have more than 20,000 employees all over the world working towards our vision of inspiring…
Added 4 hours ago
RC
Automotive Electrical Sourcing & Category Manager
Rexel Canada
Winnipeg, MB
- Full-time
…leader in energy solutions, renewables, lighting, wire & cable, automation and connected network solutions. We have access to the best partners in the industry and we go above and beyond to…
Added 4 hours ago
B
Cloud Platform Engineer
Baseten
Toronto, ON
- $165,000 to $330,000 USD / year
- Full-time
Own products and projects end-to-end, functioning as both an engineer and a project manager, with a focus on user empathy, project specification, and end-to-end execution.
Added 4 hours ago
AH
Maintenance Worker III
Alberta Health Services
Camrose, AB
- Temporary
…consultation with the Facilities, Maintenance and Engineering Manager and in accordance with accepted standards, regulations and procedures. The incumbent is responsible for completing…

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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