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Added 9 mins ago
BV
Senior Manager, Social, Content & Creator Partnerships
Betstamp Ventures
Toronto, ON
- Internship
…be accountable for the results. You'll report to our Head of Operations and work with people across the whole business, from paid acquisition and retention to brand design, product and new…
Added 9 mins ago
TS
Store Associate
The Salvation Army Canada and Bermuda Territory
North Vancouver, BC
- Part-time
The role provides service to customers, sorting incoming product and assists in the ongoing retail operations of The Salvation Army Thrift Store.
Added 9 mins ago
TS
Store Associate
The Salvation Army Canada and Bermuda Territory
Milton, ON
- Part-time
The role provides service to customers, sorting incoming product and assists in the ongoing retail operations of The Salvation Army Thrift Store.
Added 9 mins ago
R&
IT Project Manager – MPW Replat
Robertson & Company Ltd.
Waterloo, ON
- Contract
Our client is a top financial institution with significant North American holdings. They have operations across most major verticals, including institutional & corporate, wealth management,…
Added 9 mins ago
G
Part-Time Key Holder - Vaughan Mills
Geox
Vaughan, ON
- Part-time
Knowledgeable in communicating all aspects of product including store collections, best sellers and seasonal product trends
Added 9 mins ago
S
Product Manager - SOTI MobiControl
SOTI
Mississauga, ON
- $110,000 to $130,000 CAD / year
- Full-time
…importantly, be part of a winning team. As the successful Senior Product Manager, you will be responsible for taking ownership of the product line life cycle from strategic planning to…
Added 9 mins ago
TI
Go-to-Market (GTM) Growth Manager
TRSB Inc.
Montreal, QC
- Full-time
TRSB looking for a Go-to-Market (GTM) Growth Manager who can turn technology, data, content and creativity into demand.
Added 9 mins ago
J
Product Manager, Agentic Products
Jetson
Kitchener, ON
- Full-time
We're building the agentic products that runs Jetson's customer operations - and we need a product leader for it. As a Product Manager on the Agentic Products team, your customers are…
Added 24 mins ago
Product Manager, Agentic Products
Jetson Home
Kitchener, ON
We're building the agentic products that runs Jetson's customer operations - and we need a product leader for it. As a Product Manager on the Agentic Products team, your customers are…
Added 24 mins ago
Area Manager II, YXU1
Amazon
St. Thomas, ON
Our WW Operations network delivers millions of packages and smiles to Amazon customers every day. We are looking for motivated, customer-focused individuals who want to join our team as an…
Added 24 mins ago
SD
Assistant Front Store Manager, Hourly Full Time Day
Shoppers Drug Mart
Thunder Bay, ON
- Full-time
To assist the Front Store Manager (FSM) in managing the human, physical and financial resources of the store and in ensuring that store objectives are achieved by focusing on improving…
Added 24 mins ago
W
(CAN) Produce Department Manager
Walmart
Westbank, BC
- Full-time
The Produce Department Manager at Walmart leads produce associates and oversees department processes to ensure high customer service and meet production targets. Responsibilities include…
Added 24 mins ago
LC
Deli Department Manager
Loblaw Companies Limited
Nanaimo, BC
- Full-time
Oversee the day-to-day operations of a specific department within a store
Added 24 mins ago
Visual Lead (Full - Time) - Oakridge Centre
ALO
Vancouver, BC
Maintains strategic product presentation and merchandising by ensuring product recovery, restock, destock, and making visual merchandising change in accordance with directive and with…
Added 39 mins ago
TG
Area Manager/ Chef de section
The Goodyear Tire & Rubber Company
Salaberry-de-Valleyfield, QC
- Full-time
Maintain the smooth and timely flow of plant production ensuring a quality product is delivered to the next operation and customer. Achieve the business goals of the operation including…
Added 39 mins ago
Store Manager - West Edmonton Mall
Laura Canada
Edmonton, AB
As a role model and business leader, the Laura Canada Store Manager possesses a contagious passion for fashion and customer service. You will motivate and develop a winning teamthat…
Added 39 mins ago
Project Manager
ERCO Worldwide
Saskatoon, SK
ERCO Worldwide is looking for a Project Manager to join our Saskatoon team! The Project Manager leads development and execution of projects to improve process safety, operations,…
Added 39 mins ago
R
Manager, Wholesale Financial Control
RBC
Toronto, ON
- Full-time
As a Manager, Wholesale Financial Control, you will be part of the Global Markets Finance team, covering RBC's Central Funding Group. This role creates a collaborative environment with…
Added 39 mins ago
AL
AltaGas - Operator 3, Sundre
AltaGas Ltd.
Sundre, AB · PEC Sundre
- Full-time
…Partnership team in Sundre, Alberta. Reporting to the Assistant Plant Manager, this position is responsible for supporting the safe and reliable operation of the Sundre fractionation plant…
Added 39 mins ago
NB
Manager Custody Client Services
National Bank of Canada
Toronto, ON
- Full-time
You will work closely with operations, technology, product, and relationship management teams to ensure an exceptional client experience.
Added 39 mins ago
B
Senior Director, Learning & Development
BGBx
Canada
- Full-time
…engage stakeholders, and drive meaningful results throughout the product lifecycle. The work is complex, fast-moving, and deeply connected to improving lives, creating opportunities for…
Added 39 mins ago
TS
Thrift Store Clerk
The Salvation Army in Canada
Yarmouth Indian Reserve No. 33, NS · Yarmouth, NS
- Full-time
The role provides service to customers, sorting incoming product and assists in the ongoing retail operations of The Salvation Army Thrift Store.
Added 39 mins ago
NM
Marketing Manager
Neeralta Manufacturing Inc.
Barrhead, AB
- Full-time
Role Description The Marketing Manager is a full-time, on-site position based in Barrhead, AB. This role is responsible for planning and executing marketing strategies that promote…
Added 39 mins ago
SC
Food Safety Program Manager
Sysco Canada Inc.
Toronto, ON · Greater Toronto Area, Canada
- Full-time
Handles and oversee the product recall process to ensure timely communication and execution of product recalls and completion of related documentation.
Added 39 mins ago
L
5798 - Seasonal Sales Help
Lids
Windsor, ON
- $17.95 USD / hour
- Temporary
…for an exceptional Lids experience, maintain our meticulous product presentations, and be a subject matter expert in our products and…

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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