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Added 10 mins ago
Software Engineer, AI Entries
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…allows team members to take off as much time as they need (with manager approval). Hourly team members get 15 days paid time off, with an additional day for each year of…
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Wawanesa Insurance

Manager, Underwriting - Programs & Operations - WSI

Toronto, ON, Canada
North York - Toronto, ON (Hybr, ON, Canada

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Job details

Posting language: English
Posted: Oct 28, 2026

Original job description

Job ID: 10456

Employment Type: New Role

Working Business Language: English. This role is considered a head-office role and will be required to communicate with internal stakeholders across Canada where the primary business language utilized is English.

Salary: At WSI™, A Wawanesa™ Company, salary is only one component of a holistic, comprehensive, and competitive offering that we provide to our employees. In addition to salary, full-time and part-time permanent employees are eligible for an annual bonus plan and leave of absence top-up programs, and are provided with generous vacation time, personal days, premium-free benefits, and a pension plan.

The salary offered for this role is determined with consideration to various factors, including but not limited to: your work location, local labour market conditions, external market salary data, internal pay equity and the knowledge, skills, experience and anticipated proficiency in the role. The salary offered is estimated to be within the following range: $120,000- $160,000. Candidates with salary expectations outside of the range are still encouraged to apply.

About WSI
WSI is a specialty insurer within the Wawanesa group of companies, helping Canadian organizations navigate complex risk to thrive in a changing world. Working closely with its distribution partners and clients, WSI combines deep expertise, disciplined underwriting, and responsive decision-making with a relationship-led approach to deliver tailored insurance solutions built around unique needs.

Acquired by Wawanesa in 2026, WSI offers the agility of a specialty insurer backed by the strength and stability of one of Canada’s largest mutual insurance companies. Learn more at wsi.wawanesa.com.

We are currently seeking dedicated, driven, and enthusiastic individuals who thrive in a dynamic environment, embrace change, and are eager to gain diverse experience while advancing their careers as part of a growing team.

Job Overview

The Manager, Underwriting – Programs & Operations leads underwriting, portfolio management, reinsurance coordination and operations for the Programs division. The role ensures business meets approved appetite, authority, pricing, coverage, capacity and reinsurance requirements while supporting sustainable, profitable performance.

Job Responsibilities

Lead, coach and develop underwriting and operations staff, setting clear objectives, accountability, technical standards and documentation expectations.
Identify operational requirements, resources, workflows and service expectations for new programs.
Make underwriting decisions on appetite, pricing, coverage, terms, limits, deductibles, capacity and risk selection; ensure delegated activities follow approved parameters and standards.
Develop and communicate program guidelines, authorities, referrals and controls.
Manage portfolio performance using premium, rate, exposure, retention, growth, concentration, claims and loss trends; implement corrective actions.
Partner across functions on portfolio analysis, planning, forecasting and reporting.
Monitor concentrations and accumulations with CAT Modeling.
Coordinate facultative reinsurance and provide recommendations and portfolio updates to senior leadership.
Support treaty design, placement, renewal and administration with Reinsurance stakeholders.
Monitor reinsurance capacity, use, accumulation and data needs; escalate constraints.
Oversee program onboarding, policy administration, documentation, data exchange, bordereaux, premium processing and reporting.
Improve workflow efficiency, data quality, controls, service consistency and scalability.
Align and document underwriting and operating procedures; coordinate resolution of delivery issues.
Support audit scoping, policy selection and remediation of underwriting or operations findings.
Collaborate on catastrophe and accumulation actions and partner engagement.
Assess prospective MGAs, Program Administrators and opportunities with Strategy & Distribution while supporting existing relationships.
Support Contingent Profit Commission arrangements and partner business reviews; document and complete agreed actions.
Promote a collaborative, inclusive, results-focused culture balancing underwriting discipline and responsive partner service.
Other duties as assigned.

Qualifications

Significant commercial underwriting experience involving Programs, MGAs, Program Administrators, delegated authority or specialty business.
Experience exercising underwriting authority and managing a commercial portfolio.
Knowledge of facultative and treaty reinsurance.
Experience leading teams and coordinating underwriting and operational work.
Strong analytical, financial, negotiation, decision-making and executive communication skills.
Ability to collaborate with governance, distribution, control and support functions.
Canadian Programs, Affinity, Fronting or Specialty insurance experience preferred.
Experience onboarding and managing delegated underwriting arrangements preferred.

Diversity, Equity, Inclusion & Belonging

At WSI, we are committed to Diversity, Equity, Inclusion and Belonging (DEIB) and believe that our strength lies in the diversity of our people – this is supported by having a representative workforce.

We welcome applications from all qualified candidates, including racialized persons, women, Indigenous Peoples, persons with disabilities, members of the 2SLGBTQIA+ community, gender-diverse, and neurodiverse individuals, and anyone who can contribute to the further diversification of thought and ideas.

We aim to ensure our recruitment process is accessible to all candidates. If you require accommodations during any stage of the recruitment process, please reach out in confidence to jobs@wawanesa.com.

All job applicants are subject to our Employee privacy policy.

Please note that the recruitment process for this position may involve the use of AI tools to screen, assess, or select applicants. All final decisions are taken or reviewed by human recruiters and human hiring leaders in compliance with all applicable legislation.

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More about this job

Responsibilities

The Manager leads underwriting, portfolio management, and operations for the Programs division to ensure sustainable and profitable performance. They are responsible for coaching staff, setting technical standards, and managing reinsurance coordination and program guidelines.

Requirements

Candidates must have significant commercial underwriting experience, particularly with Programs, MGAs, or specialty business. Strong analytical, leadership, and financial skills are required, along with knowledge of facultative and treaty reinsurance.

Skills

Commercial underwriting
Portfolio management
Reinsurance coordination
Operations management
Team leadership
Risk selection
Financial analysis
Negotiation
Executive communication
CAT modeling
Program administration
Data quality management
Strategic planning
Stakeholder management
Underwriting authority

Benefits

Annual bonus plan
Leave of absence top-up programs
Generous vacation time
Personal days
Premium-free benefits
Pension plan

Visa sponsorship

Not detected in the job text

Keywords

Underwriting
Programs
Operations
Portfolio Management
Reinsurance
Facultative Reinsurance
Treaty Reinsurance
MGA
Program Administrators
Risk Selection
CAT Modeling
Policy Administration
Bordereaux
Contingent Profit Commission
Commercial Insurance
Specialty Insurance
Delegated Authority
Financial Forecasting
Data Analysis
Stakeholder Engagement
Underwriting Discipline
Insurance Solutions
Risk Management
Capacity Management
Regulatory Compliance

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