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Added 43 mins ago
NA
Account Coordinator, Commercial SME
NFP, an Aon company (Canada)
Newmarket, ON
- Full-time
Added 4 hours ago
KG
Multifamily Property Accountant (Toronto)
Kipling Group
Toronto, ON
- Full-time
Company Overview: Kipling is one of Canada’s largest and most successful independent full-service property management companies. Our core focus is property management – both commercial and…
Added 4 hours ago
CC
Public Service Authority - Executive Director
Carroll County, Virginia
ON · Regional Municipality of York, ON
- Full-time
Works with regulatory agencies, engineers, attorneys, consultants, contractors, developers, businesses and property owners on Authority projects and issues.
Added 4 hours ago
G
Shield Program Lead
Guesty
Canada
- Full-time
…Booking.com, Expedia, Google Travel, and many more - Guesty empowers property managers to deliver top-tier guest experiences while running more efficient, data-driven…
Added 8 hours ago
T
General Counsel
Techo-Bloc
Longueuil, QC · Saint-Hubert, Quebec
- Full-time
Review key contracts - insurance, employment, warranty, customer, lease, supplier, service, confidentiality, and other commercial agreements - and identify gaps, risks, and template…
Added 10 hours ago
IG
Commercial Lines Account Professional
Insight Global
Ottawa, ON · Kanata, ON
- $65,000 to $73,000 CAD / year
- Full-time
- Identify client risks and recommend appropriate insurance solutions, including Property, Liability, Commercial Auto, Professional Liability, Cyber, and Specialty Coverages.
Added 10 hours ago
SC
Underwriting Assistant (PL)
SPG Canada
Langley (District), BC · City of Langley, BC
- Full-time
…we are still accelerating. Today we operate at scale across commercial, personal, and specialty lines, serving brokers nationwide through a broad and expanding product…
Added 10 hours ago
KR
Junior Commercial Real Estate Agent
K2 Real Estate Group
Toronto, ON · Etobicoke, ON
- Full-time
Commercial real estate is hard to learn from the outside. At K2 Commercial Group, the commercial division of K2 Real Estate Group, newer salespeople learn it by working on real transactions…
Added 11 hours ago
TR
Commercial Property Manager
Taylor Ryan Executive Search Partners
Toronto, ON · Etobicoke, ON
- $95,000 to $120,000 CAD / year
- Full-time
Our client is an established, privately traded owner-operator of commercial real estate that has been in business since the 1950's. They are hiring an experienced Commercial Property…
Added 11 hours ago
TP
Manager, Real Estate Operations
Toronto Pearson International Airport
Toronto, ON
- Full-time
…Toronto Pearson’s diverse portfolio of aviation and non-aviation commercial real estate assets. You will lead lease compliance, property operations, operating cost and recovery-rate…
Added 11 hours ago
G&
Managing Director
Groom & Associés / Associates
Montreal, QC
- Full-time
…develops industry-leading security solutions that protect people, property and business. They work with healthcare, education, manufacturing, construction, and banking…
Added 11 hours ago
B
Operations Manager
BGIS
Toronto, ON
- Full-time
▪ Meet with Property Management team, Operations team, tenants, vendors, contractors and senior management as needed to review
Added 11 hours ago
CL
General Manager - Off Campus
Campus Living Centres
Waterloo, ON
- Full-time
…projects, and establish priorities consistent with company and property objectives, as well as liaise with senior managers of…
Added 11 hours ago
SR
Commercial Property Manager
Servis Realty Inc.
AB · Edmonton, AB
- Full-time
Servis Realty Inc. is seeking an experienced Commercial Property Manager to
Added 11 hours ago
SR
Commercial Property Manager - Industrial
Servis Realty Inc.
AB · Edmonton, AB
- Full-time
Commercial Property Manager - Suburban Office & Industrial
Added 11 hours ago
C
Senior Property Manager
CBRE
Toronto, ON
- Full-time
CBRE Group, Inc. (NYSE:CBRE), a Fortune 500 and S&P 500 company headquartered in Dallas, is the world’s largest commercial real estate services and investment firm (based on 2024 revenue).…
Added 11 hours ago
RH
Property Manager
Robert Half
BC · Fraser Valley, BC
- Full-time
Previous experience in commercial or multi-residential property management, ideally with responsibility for an established property portfolio.
Added 11 hours ago
SR
Accounting Technician - Accounts Payable & Receivable
Servis Realty Inc.
AB · Edmonton, AB
- Full-time
Accounting experience in property management or commercial real estate.
Added 11 hours ago
VC
Director of Property Management
Villa Charities Inc.
Toronto, ON · North York, ON
- $115,000 to $140,000 CAD / year
- Full-time
Reporting directly to the Chief Executive Officer (CEO), the Director, Property Management provides strategic leadership and operational oversight for Villa Charities' diverse property…
Added 11 hours ago
T
SAP Finance Domain Architect
Talan
Toronto, ON
- $170,000 to $200,000 CAD / year
- Full-time
Design SAP Finance solutions, prepare estimates, and contribute to commercial proposals in partnership with Sales and Delivery teams.
Added 11 hours ago
C
Senior Facilities Manager
CBRE
Richmond, BC
- Full-time
…facilities management services across a complex portfolio of commercial, industrial, critical environment, healthcare, or institutional facilities. You will serve as the primary strategic…
Added 11 hours ago
MV
Clerk-Regional Housing
Metro Vancouver
Burnaby, BC
- Full-time
Completion of the 12th school grade including or supplemented by commercial courses, plus sound property management clerical experience or an equivalent combination of training and…
Added 11 hours ago
C
Executive Assistant
CURIE
Burlington, ON
- Full-time
CURIE (Canadian Universities Reciprocal Insurance Exchange) delivers cost effective, and solutions based, commercial insurance and risk management services to its members; Canadian…
Added 12 hours ago
G
Client Solutions Manager
Gallagher
Calgary, AB
- Temporary
We are seeking a highly motivated Commercial Lines Account Manager with a minimum of 3 years of experience and demonstrated expertise in Construction and Contractor risks to support a…
Added 12 hours ago
A
Property Accountant Administrator
Adecco
Toronto, ON
- $28 to $30 CAD / hour
- Temporary
We are currently recruiting for an experienced Property Accounting Administrator to join a busy commercial property management team in downtown Toronto for a confirmed 12-month maternity…

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.

Apply About employer

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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