Lead Executive Claims Analyst

Wawanesa Insurance; Winnipeg; Hybrid; CAD 90,000 - 115,000; Full time

Benefits offered by this job

Annual bonus plan

Leave top-up programs

Generous vacation time

Benefits and pension

Job summary

The Wawanesa Mutual Insurance Company is seeking a Lead Executive Claims Analyst to drive initiative delivery, align business objectives with stakeholder needs, and guide system and process enhancements across Canada. You will lead projects, manage risks, and ensure timely, high‑quality outcomes while applying agile and lean six sigma methodologies.

With strong leadership, analytical acumen, and excellent communication, you will engage regional teams, mentor staff, and partner with vendors to

Qualifications

• Seven years of property and casualty insurance experience or business analysis.
• Post-secondary degree or certificate or equivalent experience.
• Completed CIP or equivalent Business Analysis designation.
• Strong leadership with ability to identify and act on strategic opportunities.
• Advanced analysis and conceptual thinking for detailed information.
• Strong communication, presentation, and negotiation skills with diverse audiences.

Responsibilities

• Create, execute, and monitor initiative management plans and schedules.
• Define and manage scope, risks, and issues across the initiative lifecycle with leads.
• Evaluate current baselines to determine benefits.
• Engage regional teams, ensure quality, and meet initiative objectives.
• Maintain initiative repository for communication and transparency.
• Lead analysis and design of system and business requirements for enhancements.
• Provide regular status reporting to stakeholders.
• Lead presentations of initiatives to multiple business groups.
• Anticipate bottlenecks, escalate appropriately, balance business and tech needs.
• Follow agile practices and lean six sigma methodologies.

Skills

Leadership

Communication

Agile practices

Stakeholder management

Project management

Team collaboration

Bilingual (asset)

Education

Post-secondary degree

CIP designation

Tools

Microsoft Office Suite

JIRA

Confluence

Microsoft Teams

Mitchell/ERAC/Xactware/Progi/HCAI integrations

Job description

Job ID: 10236

Employment Type: Existing Role

Work Environment: We offer a hybrid work environment that offers flexibility to our employees in balancing in-office (2 days per week OR 15 hours per week in a Wawanesa office) and remote work. You may work from any of the following locations: Winnipeg, MB; Wawanesa, MB; Vancouver, BC; Calgary, AB; Edmonton, AB; Lethbridge, AB; Toronto (North York), ON; Kitchener, ON; Ottawa, ON; Montreal, QC; Quebec City, QC, Moncton, NB; Dartmouth; NS.

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 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. The salary offered is estimated to be within the following range: $90,000 - $115,000. Candidates with salary expectations outside of the range are still encouraged to apply.

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

Working under minimal supervision, the Lead Executive Claims Analyst will contribute to Wawanesa’s success by applying their perceptive analytical skills to understand the objectives of our business, requirements of our stakeholders, and advancements in technology to lead the delivery of claims solutions that enable exceptional claims experience for our members and end users. The right candidate for this role will have experience in leading projects or initiatives to deliver on desired results.

Job Responsibilities

• Create, execute, and monitor initiative management plans and schedules.
• Work with Claims and IS Leaders to define and manage scope, risks, and issues throughout the initiative life cycle.
• Evaluate current state baselines to determine organizational/strategic benefits.
• Engage regional business teams, manage quality of the delivered solution, ensuring all initiative objectives are met.
• Maintain initiative repository to enhance communication, allow for tracking, and ensure transparency.
• Lead the analysis and design of both system and business requirements for application enhancements and initiatives.
• Create and communicate regular status reporting to all stakeholders
• Lead the creation and delivery of initiative presentations to multiple business groups.
• Anticipate bottlenecks, provide escalation management, and balance the business needs versus technical constraints.
• Follow agile practices and lean six sigma methodologies.
• Communicate system solutions in business and technical terms.
• Analyze business processes for opportunity for improvement by eliminating waste and implementing changes.
• Manage relationships and work efforts of third-party vendors and consultants specifically related to assigned work.
• Leverage software development tools, such as JIRA, Confluence and Microsoft Teams
• Provide business value impact to assist in the prioritization of the work
• Lead OCM support on initiatives by creating training material and providing demos and training staff as required.
• Engage Regional Offices to ensure a complete understanding of business deliverables is accomplished
• Develop and enhance productive business relationships by liaising with internal and external stakeholders
• Coach, mentor and train team members.
• Perform other duties as assigned.

Qualifications

• Minimum seven years of property and casualty insurance experience or business analysis.
• Completion of post-secondary degree/certificate or equivalent experience
• Completed CIP or equivalent Business Analysis designation
• Strong leadership skills with the ability to continuously identify and action strategic opportunities for the initiative team and organization.
• Advanced analysis and conceptual thinking skills with the ability to conduct detailed analysis of information, and to select and implement best solutions.
• Advanced communication, presentation, and negotiation skills, with the ability to communicate in a clear and concise manner with style fitting for the audience and message.
• Advanced planning, organizing and time management skills, with the ability to develop and implement plans by prioritizing and multitasking.
• Ability to support high team morale by encouraging others to be excited, motivated, and enthusiastic about initiative activities and outcomes.
• Proven ability to work collaboratively in a team environment.
• Strong leadership skills to provide support and guidance to team members.
• Strong working knowledge of Microsoft Office Suite
• Experience using integrations such as Mitchell, ERAC, Xactware, Progi, HCAI, and AI
• Proven experience in agile practices, scrum, Kanban, lean six sigma methodologies and continuous delivery.
• Proven experience on corporate strategic initiatives or projects.
• Bilingual 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 [e-mail].

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.