Senior Organizational Change Management Specialist

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Date: Sep 2, 2026

Location: Winnipeg, MB (Hybrid), CA Moncton, NB (Hybrid), CA Calgary, AB (Hybrid), CA Edmonton, AB (Hybrid), CA North York - Toronto, ON (Hybr, CA Ottawa, ON (Hybrid), CA Kitchener, ON (Hybrid), CA Vancouver, BC (Hybrid), CA Dartmouth, NS (Hybrid), CA

Company: Wawanesa Insurance

Job ID: 10294 


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; Vancouver, BC; Calgary, AB; Edmonton, AB; Toronto (North York), ON; Kitchener, ON; Ottawa, ON; Moncton, NB; Dartmouth; NS. 

 

Working Business Language: 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

The Senior Organizational Change Management Specialist partners with business leaders, program teams, and stakeholders to enable successful adoption of strategic, operational, technology, and transformational change initiatives across Wawanesa.

 

As part of the Strategy Office, this role applies organizational change management expertise to assess readiness, identify adoption risks, influence leadership actions, and support sustainable business outcomes. The role balances hands-on delivery with strategic advisory services, helping leaders build change capability while contributing to the evolution of Wawanesa's enterprise OCM practice.

 

The successful candidate will work across multiple initiatives and business areas, leveraging change insights, stakeholder engagement, leadership coaching, and data-informed recommendations to support organizational readiness, adoption, and long-term value realization.

Job Responsibilities  

  • Lead OCM activities for complex enterprise initiatives, programs, and transformational efforts.
  • Conduct change impact, stakeholder, readiness, and adoption assessments to inform OCM strategies.
  • Develop and execute integrated change plans aligned to business objectives, delivery milestones, and organizational needs.
  • Identify change risks and develop mitigation strategies that support successful implementation and sustainment.
  • Partner with leaders to strengthen sponsorship effectiveness and change leadership capabilities.
  • Coach leaders on navigating resistance, building commitment, and reinforcing desired behaviours.
  • Support leadership teams in clarifying change narratives and mobilizing stakeholders through periods of uncertainty.
  • Facilitate stakeholder workshops, leadership discussions, impact assessments, readiness reviews, and alignment sessions to support initiative objectives.
  • Gather and interpret qualitative and quantitative change-related data to assess organizational readiness and adoption.
  • Develop meaningful insights and recommendations that support prioritization, sequencing, and decision-making.
  • Contribute to change capacity and saturation assessments that help leaders understand cumulative impacts across the organization.
  • Build trusted relationships with operational leaders, program teams, Communications, Learning & Development, People Team, and other partners.
  • Partner with project and program leaders to integrate change management considerations into governance, planning, and decision-making processes.
  • Contribute to the ongoing evolution of Wawanesa's OCM methodology, tools, templates, and governance processes.
  • Promote consistent, fit-for-purpose change management practices across initiatives.
  • Help establish OCM as a trusted strategic partner by demonstrating measurable business value and organizational impact.

Qualifications

  • Bachelor's degree in Business, Organizational Development, Human Resources, Psychology, Communications, Commerce, or a related discipline.
  • 7-10+ years of experience leading organizational change management activities within complex organizations.
  • Demonstrated success supporting enterprise-wide business, technology, operational, or transformation initiatives.
  • Change Management certification (Prosci, CCMP, or equivalent) is considered an asset.
  • Strong knowledge of change management principles, methodologies, and leading practices.
  • Experience conducting stakeholder assessments, change impact assessments, readiness assessments, and adoption measurement.
  • Ability to influence and build credibility with leaders at multiple organizational levels.
  • Strong facilitation, coaching, communication, and relationship management skills.
  • Experience translating data and insights into actionable recommendations.
  • Strong analytical, problem-solving, and strategic thinking capabilities.
  • Comfortable working in ambiguity and helping shape emerging processes and capabilities.
  • Experience working within project, program, or portfolio delivery environments.
  • Proficiency in Microsoft 365 tools and experience leveraging collaboration, visualization, reporting, and AI-enabled technologies to support change outcomes.


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 jobs@wawanesa.com.
 

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.