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AA
Vice President, Business Development
AIP Asset Management
Winnipeg, MB · Greater Winnipeg Metropolitan Area
- Full-time
…strategies outside traditional public equity and fixed-income…
Added 1 min ago
Program Manager, Product Change and Development
Westerkirk
Calgary, AB · Mississauga, ON
…across British Columbia, Alberta and Ontario, as well as in markets and distribution hubs…
Added 1 min ago
S
CRM Analyst
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- Full-time
2 to 3 years of experience in CRM administration, business systems analysis or investment operations, ideally within alternative asset management, private markets or financial services.
Added 15 mins ago
A
Process Engineering Team Lead
AtkinsRéalis
Toronto, ON
- Full-time
…technical leadership, project delivery, talent development, and business growth while delivering high-value engineering solutions across industrial manufacturing, chemicals, energy…
Added 30 mins ago
PC
Information Systems & Technical Support
Patterson Companies, Inc.
Cambridge, ON
- Full-time
…products to the pet retail, veterinary, agricultural, and equine markets across…
Added 30 mins ago
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Business Development Manager, GTA
Digicast
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- Full-time
The Business Development Manager – Toronto Market is responsible for driving new business, developing and nurture strategic relationships in the GTA, and positioning Digicast as the premier…
Added 30 mins ago
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Représentant(e) Ventes internes/Inside Sales Representative
ADP
Montreal, QC
- Full-time
Added 1 hour ago
SA
Commercial insurance account manager
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Levis, QC
- Full-time
Hold a business damage insurance license issued by the Financial Markets Authority;
Added 1 hour ago
SA
Commercial insurance account manager
Synex Assurance
Quebec, QC
- Full-time
Hold a business damage insurance license issued by the Financial Markets Authority;
Added 1 hour ago
SA
Commercial insurance account manager
Synex Assurance
Quebec, QC
- Full-time
Hold a business damage insurance license issued by the Financial Markets Authority;
Added 2 hours ago
RC
Automotive Electrical Sourcing & Category Manager
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- Full-time
…residential and commercial sectors. As energy evolves, our business is transforming alongside it. This change is driven by you - our fresh thinkers, innovators and groundbreakers. By…
Added 2 hours ago
NB
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 2 hours ago
NB
Senior Analyst - SSI Expert
National Bank of Canada
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…of approximately 160 colleagues and report to an Operations Manager. Our team stands out for its expertise in derivative products and settlement processes, its collaborative mindset, and…
Added 2 hours ago
Salesforce Technical Architect - Financial Services Cloud, Marketing Cloud & Data360 - Manager
EY
Toronto, ON · Montreal, QC
…working closely with clients and delivery teams to translate business needs into scalable Salesforce…
Added 3 hours ago
EG
Business Development Manager - Power Transmission
EMAGE Group
Canada
- Full-time
Business Development Manager / Director - Power Transmission
Added 4 hours ago
RP
Counter Sales Representative
Reliable Parts Ltd.
Calgary, AB
- Full-time
We are a leading distributor of appliance parts in the US and Canadian markets. With over 60 branch locations and multiple distribution centers, we provide service to customers in multiple…
Added 4 hours ago
H
Global Mining Practice Business Development Leader
HDR
Corner Brook, NL
- Full-time
Lead Mining Practice Growth: Establish and execute a global business development strategy that grows bookings, revenue, backlog and market share in priority mining markets.
Added 4 hours ago
H
PPC Manager
Huzzle
Remote, Canada
- Full-time
- Remote
We are looking for an experienced and results-driven PPC Manager (Pay-Per-Click Manager) to join a growing digital marketing team.
Added 4 hours ago
G
Shield Program Lead
Guesty
Canada
- Full-time
…transforming how the industry works - from guest experience to business…
Added 6 hours ago
G
Strategic A&E Consultant Manager - Canada
Gallagher
Montreal, QC · Greater Montreal Metropolitan Area
- Full-time
As Strategic A&E Consultant Manager, you'll strengthen Gallagher Security's position within the Canadian architecture, engineering, and security consultant community. Given the bilingual…
Added 6 hours ago
RD
Data Creation Analyst - Entry Level
Randstad Digital
Toronto, ON · Greater Toronto Area, Canada
- Full-time
Reporting directly to the Operations Manager, the Data Creation Analyst will be responsible for generating proprietary data by retrospectively analyzing video footage of sporting events…
Added 6 hours ago
CO
Growth Coordinator
City of Saint John
Saint John, NB
- Full-time
…of Saint John and under the direct supervision of the Growth Manager, the Growth Coordinator will be a champion for growth in Saint…
Added 6 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 6 hours ago
TS
Business Development Manager
TalentSphere Staffing Solutions
Markham, ON
- Full-time
Business Development Manager (Heavy Civil Construction)
Added 6 hours ago
AC
Data Analytics Manager
Amphenol Communications Solutions
Markham, ON
- Full-time
…Communications, Mobile, RF, Optics, and Commercial electronics markets. Amphenol Corporation is one of the world’s largest designers and manufacturers of electrical, electronic and fiber…

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

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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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