Date: Jul 28, 2026
Location: Winnipeg, MB (Onsite), CA Montreal, QC (Hybrid), CA Edmonton, AB (Hybrid), CA Calgary, AB (Hybrid), CA North York - Toronto, ON (Hybr, CA
Company: Wawanesa Insurance
Job ID: 10234
Employment Type:
Existing Role
Work Environment: This role can be performed from the following locations: Calgary, AB; Edmonton, AB; Toronto (North York), ON; Montreal, QC; Winnipeg, MB.
Candidates located in Winnipeg, MB are required to be physically onsite 5 days/week whereas alternate locations are required to be physically onside at least 3 days / week.
Working Business Language : English. This role is considered a head-office role and will be required to communicate with internal and external stakeholders across Canada where the primary business language for this role is English. As such, the successful candidate must be fully proficient in English.
Salary: At Wawanesa, 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, leave of absence top-up programs and provided with generous vacation time, personal days, premium free benefits and 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.
About The Wawanesa Mutual Insurance Company
Founded in 1896, The Wawanesa Mutual Insurance Company is one of Canada’s largest mutual insurers, 100% owned by its members, with more than $4.1 billion in annual revenue and $12.5 billion in assets. Headquartered in Winnipeg, Wawanesa is the parent company of Wawanesa Life, which provides life insurance solutions throughout Canada, and Western Financial Group, a leading national distributor of personal and business insurance. In March of 2026, Wawanesa entered into an agreement to acquire Everest Insurance Company of Canada to strengthen its commercial insurance capabilities and advance its long-term growth strategy.
Wawanesa proudly serves more than 1.8 million members and we are home to more than 3,000 employees across Canada. The company actively gives back to organizations that strengthen communities, donating more than $4 million annually to charitable organizations, including more than $2 million each year in support of people on the front lines of climate change. Learn more at wawanesa.com.
We are currently looking for dedicated, driven, and enthusiastic individuals who thrive in an environment that welcomes change and are looking for an opportunity for diverse experience and advancement on a growing team.
Job Overview
The Vice President, Legal & General Counsel is the enterprise functional leader for Wawanesa’s Legal teams. Reporting to the SVP, Chief Legal & Strategy Officer, the role is accountable for the effective operation, coordination, capability, delivery and continuous improvement of legal services across Wawanesa.
The role ensures Wawanesa’s Legal function delivers practical, timely, consistent, business-savvy and risk-informed advice across the enterprise. The role operates within the enterprise legal strategy, governance expectations and escalation protocols established by the SVP, Chief Legal & Strategy Officer, and supports that office on material enterprise, governance, strategic transaction, regulatory, reputational and Board-related matters as requested.
Job Responsibilities
Enterprise Legal Function Leadership
Lead Wawanesa's Legal function, including legal service delivery, legal operations, talent, practice management, external counsel management and functional effectiveness.
Implement enterprise legal strategy through functional plans, operating routines, practice standards, work allocation and performance expectations.
Build and maintain an engaged, capable and collaborative Legal team that delivers practical, commercially aware and risk-informed advice aligned with Wawanesa's values and enterprise priorities.
Legal Service Delivery and Operations
Design and oversee Legal operating routines, including matter intake, triage, prioritization, assignment, escalation, reporting and closure practices.
Establish service standards, performance measures, knowledge management practices and continuous improvement initiatives that support timely, consistent and high-quality legal support.
Maintain visibility over significant legal matters, demand drivers, capacity pressures and emerging legal risks.
Legal Advice, Matter Management and Escalation
Provide senior legal advice and oversight on assigned corporate, commercial, insurance, regulatory, governance, employment, litigation, privacy, technology and transaction matters.
Oversee legal support for material disputes, investigations, regulatory matters, commercial arrangements and enterprise initiatives.
Ensure material legal, regulatory, governance, strategic, financial, operational and reputational matters are identified, managed and escalated appropriately, while helping business leaders understand legal considerations, options, trade-offs and implementation implications.
External Counsel and Resource Management
Oversee external counsel selection, engagement, performance, budgeting, billing discipline and value management.
Establish expectations for the use of external counsel, matter scoping, advice integration and knowledge transfer, and monitor legal spend and resource effectiveness.
Qualifications
LLB, JD or equivalent law degree and membership in good standing with a Canadian law society or other applicable law society.
A minimum of 12 years of professional legal experience, including significant experience in a complex corporate, insurance, financial services or regulated environment.
Demonstrated experience leading legal teams, legal operations, matter management, functional planning, external counsel management and legal service delivery at scale.
Strong knowledge across multiple legal disciplines relevant to Wawanesa, such as corporate/commercial, insurance, regulatory, privacy, employment, litigation, intellectual property, technology, governance, transactions and risk-related legal matters.
Experience advising senior leaders and translating legal analysis into practical business-oriented guidance.
Experience developing legal talent, strengthening team capability and building effective professional standards and operating routines.
Business, governance, risk management, compliance, insurance or leadership education, such as an MBA, LLM, ICD.D or equivalent senior business experience, is an asset.
Diversity Equity, Inclusion & Belonging
At Wawanesa, 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
[email protected] .
All Wawanesa job applicants are subject to Wawanesa's 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.
