Senior Product Development Specialist, (Personal Lines)

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Date: Sep 3, 2026

Location: Winnipeg, MB (Hybrid), CA

Company: Wawanesa Insurance

Job ID: 10293 


Employment Type: New 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; Montreal, 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: $100,000 - $120,000. 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

This senior role is accountable for leading complex, high-impact product innovation initiatives across Personal Lines, from concept through stable release and post-launch optimization. The role serves as a senior individual contributor and trusted advisor, providing strategic guidance, influencing enterprise decisions, and leading initiatives that span multiple business units, operational functions, and technology domains.

Job Responsibilities

  • Stakeholder Leadership: Lead alignment across business, technology, operational, compliance, and external partner stakeholders on complex product innovation priorities. Influence senior leader decision-making and provide strategic recommendations regarding prioritization, scope, investment decisions, implementation approaches, and business value realization.
  • Strategic Solution Shaping: Translate product innovation strategies and business cases into scalable delivery approaches, operating models, success measures, and implementation plans. Evaluate complex business opportunities and emerging capabilities, balancing member value, operational impact, financial outcomes, technical feasibility, and organizational readiness.
  • Complex Delivery Oversight: Oversee multiple enterprise-impacting initiatives while proactively managing dependencies, capacity constraints, risks, milestones, and scope trade-offs across portfolios. Provide executive-ready visibility into progress and recommend actions to optimize delivery outcomes.
  • Quality, Testing & Governance: Establish expectations for quality assurance, user acceptance testing, release governance, approvals, and audit-ready documentation. Own the continuous improvement of governance practices, frameworks, standards, and controls that strengthen delivery effectiveness, consistency, and compliance.
  • Operational Readiness Leadership: Lead readiness planning for complex or higher-risk launches, ensuring operational teams, business partners, technology teams, brokers, and external partners are prepared to support successful implementation, adoption, and ongoing operations.
  • Performance Strategy & Optimization: Define performance measurement strategies and lead post-launch reviews that connect outcomes to business case objectives, operational results, member and broker experience, and financial performance. Analyze trends across initiatives to identify optimization opportunities, emerging risks, and strategic recommendations.
  • Vendor & Partner Leadership: Provide oversight of strategic vendor and partner relationships, including delivery performance, implementation milestones, contractual requirements, data and privacy considerations, and issue resolution. Manage matters that carry significant business, operational, financial, or reputational risk.
  • Coaching & Practice Improvement: Serve as a senior subject matter expert and trusted advisor for Product Innovation delivery practices. Mentor Product Development Specialists, establish best practices and reusable methodologies, contribute to capability development and succession planning, and act as an escalation point for complex delivery, stakeholder, and governance matters.

Qualifications

  • 8+ years of progressively responsible experience in product, product delivery, product operations, or related insurance or financial services roles, preferably within P&C insurance.
  • Demonstrated success leading complex, cross-functional initiatives with enterprise impacts, multiple stakeholder groups, external partners, and measurable business outcomes.
  • Proven ability to influence strategic business decisions and secure alignment among Director, VP, and Executive stakeholders in highly matrixed environments without direct authority.
  • Strong understanding of product lifecycle delivery, operational readiness, change enablement, risk management, compliance, and post-launch performance measurement.
  • Advanced analytical capability with experience connecting KPIs, financial outcomes, operational data, customer feedback, and business case assumptions to actionable recommendations.
  • Experience establishing governance practices, improving delivery processes, and coaching peers or junior team members.
  • Experience leading enterprise-wide initiatives, large-scale transformation efforts, or strategic external partnerships.


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.
 

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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.