VP, Direct Venture Experience & Operations

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Date: Aug 11, 2026

Location: North York - Toronto, ON (Hybr, CA Montreal, QC (Hybrid), CA Kitchener, ON (Hybrid), CA Calgary, AB (Hybrid), CA Winnipeg, MB (Hybrid), CA Winnipeg, MB, CA, R3C-1P5 Ottawa, ON (Hybrid), CA

Company: Wawanesa Insurance

Job ID: 10262 


Employment Type: New Role

 

Work Environment: We offer a hybrid work environment. Executives are required to work in-office 3 days per week (all locations except Winnipeg) and 5 days per week in Winnipeg. You may work from any of the following locations: Calgary, AB; Winnipeg, MB; Wawanesa, MB; Toronto (North York), ON; Kitchener, ON; Ottawa, ON; Montreal, QC. 

 

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, Direct Venture Experience & Operations designs, builds and scales the member experience and operating capabilities required to launch and grow Wawanesa’s Direct-to-Member (D2M) business. The role owns the model for a simple, intuitive, AI-first journey across quote, bind, onboarding, service, retention and future claims interactions. As a senior venture leader, the VP translates strategy into execution by establishing the service model, decision rights, routines and cross-functional ways of working for a high-growth digital insurance business. The VP will help to define what is delivered by enterprise functions, and how capabilities mature from test-and-learn through launch, scale and steady state, with focus on member experience, service operations, AI-assisted service, partner management, fraud, training, underwriting and claims integration, and lifecycle performance.  

Job Responsibilities

  • Lead the D2M Experience & Operations strategy and operating model for a simple, accessible, compliant and scalable experience across digital and assisted channels. 
  • Establish capabilities, workflows, governance, service standards, routines, escalation paths and decision rights. 
  • Build Experience & Operations as a core venture capability, clarifying D2M-owned versus enterprise-delivered capabilities from MLP to launch and scale. 
  • Design the quote-to-bind-to-service model, including digital self-serve, AI-assisted service, licensed agent support, contact centre integration, escalation pathways and dual-licensed capabilities where applicable. 
  • Partner across product, technology, data, marketing, underwriting, pricing, claims, legal, risk, compliance and shared services to embed requirements, controls and scalability. 
  • Establish metrics for service levels, conversion, onboarding, resolution, quality, member effort, retention, NPS, complaints and risk indicators. 
  • Use feedback, data, market learnings, automation, AI decision support, analytics and workflow tools to improve speed, quality and scalability. 
  • Support fraud, risk, underwriting, claims and compliance interfaces, protecting member experience while maintaining controls. 
  • Lead readiness for products, channels, pilots, campaigns and releases, ensuring processes, training, tools, controls, reporting and support models are in place. 
  • Oversee vendor and partner management, commitments, capacity planning, issue resolution, reporting and governance. 
  • Identify operational gaps, dependencies, risks and constraints; recommend trade-offs, sequencing, investment and resourcing. 
  • Build a high-performing team and matrixed model; foster a member-first, test-and-learn culture balancing speed, discipline, readiness, resilience and growth. 
  • Ground executive decisions in what can be delivered, scaled, measured and sustained in market. 
  • Other duties as assigned.

Qualifications

  • 15+ years of leadership experience in operations, customer/member experience, digital service, insurance operations, transformation or venture-scale business builds. 
  • Senior leadership experience in insurance, financial services or another regulated environment where customer experience, controls, risk management and scalability are critical. 
  • Experience designing, launching and scaling operating models, service models and customer/member experiences in ambiguous or fast-moving environments. 
  • Understanding of direct-to-consumer or digital distribution models, including quote, bind, onboarding, servicing, retention, claims or issue-resolution journeys. 
  • Experience integrating operations across product, technology, data, underwriting, pricing, claims, legal, risk, compliance, marketing and shared services. 
  • Experience with AI-enabled, automation-enabled or digitally assisted operating models is a strong asset. 
  • Ability to define service standards, metrics, controls and routines that balance member outcomes with business discipline. 
  • Strong influence, relationship and judgment skills, including matrix leadership and balancing member experience, speed, scalability, cost, regulatory obligations and risk. 
  • Experience building teams, clarifying accountabilities, developing leaders and scaling capabilities. 
  • Knowledge of Canadian P&C insurance, contact centre, licensed agent, operational excellence, partner management, fraud or claims operations is an asset. 
  • Post-secondary degree in a related field; MBA, CIP/FCIP, Lean/Six Sigma, Agile, Product, Operations or CX certifications are assets. 

 

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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.