VP, Direct Venture Marketing

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Date: Sep 17, 2026

Location: North York - Toronto, ON (Hybr, CA Edmonton, AB (Hybrid), CA Winnipeg, MB (Hybrid), CA Hybrid - Canada, CA Calgary, AB (Hybrid), CA

Company: Wawanesa Insurance

Job ID: 10283 


Employment Type:  New Role 

 

Work Environment: We offer a hybrid work environment that offers flexibility to our employees in balancing in-office (3 days per week in a Wawanesa office) and remote work. 

 

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 Marketing develops and executes the growth and customer acquisition strategy for Wawanesa’s Direct-to-Member (D2M) business. This role builds and scales the marketing function to launch and grow a digital-first insurance offering, establishing the capabilities, partnerships, agency governance, performance disciplines, and data-driven practices needed to attract, retain, and grow members efficiently and profitably. As a key member of the D2M leadership team, the VP combines strategic leadership with hands-on execution, leading acquisition strategy, campaigns, experimentation, performance optimization, and capability building through the venture’s early stages. The role partners with Product, Technology, Analytics, Member Experience, Finance, Legal, Risk, Compliance, and enterprise Marketing to create a differentiated growth engine that supports long-term venture success.

 

Job Responsibilities

  • Achieve acquisition, growth, qualified traffic, lead generation, conversion, activation, retention, CAC, ROI, and long-term member value targets.
  • Develop and lead the D2M growth strategy, channel plans, and experimentation framework to optimize acquisition, conversion, retention, lifetime value, and marketing ROI across paid, earned, owned, partner, and emerging channels.
  • Prioritize acquisition opportunities, partnerships, and growth initiatives using market, customer, competitive, analytics, attribution, and performance data.
  • Build and scale the D2M marketing capability, including operating model, governance, technology, talent, agency support, organizational design, and investment requirements across launch and growth stages.
  • Lead selection, management, performance, contracts, scopes of work, governance, and optimization of agencies and strategic marketing partners.
  • Ensure agency and campaign activity aligns with brand standards, member experience, regulatory requirements, venture objectives, ROI targets, and trust-building member experiences.
  • Oversee integrated campaigns across search, social, content, email, partnerships, automation, personalization, AI-enabled marketing, and digital acquisition channels.
  • Partner with Product, Technology, UX, Analytics, Member Experience, enterprise Marketing, Legal, Risk, Compliance, and Finance to optimize journeys, onboarding, conversion, retention, and compliant growth solutions.
  • Provide executive guidance on acquisition performance, customer trends, growth opportunities, investment priorities, go-to-market decisions, and business cases.
  • Build and develop a high-performing team and internal/external ecosystem that fosters accountability, innovation, collaboration, learning, coaching, performance, and a data-driven growth culture aligned to venture objectives.

Qualifications

  • 12–15+ years of progressive marketing leadership experience, including customer acquisition, growth, performance marketing, demand generation, and scaling digital, direct-to-consumer, or digitally enabled businesses.
  • Experience building functions, teams, or capabilities in emerging, high-growth, or transformational environments.
  • Experience managing agency relationships, marketing budgets, partners, and significant marketing investments.
  • Expertise in digital channels, growth strategy, acquisition funnels, marketing analytics, attribution, experimentation, conversion optimization, CRM, automation, customer data platforms, and AI marketing tools.
  • Strong financial and commercial acumen; regulated industry experience preferred; insurance or financial services is an asset.
  • Bachelor’s degree in Marketing, Business, Commerce, Communications, or related field; MBA or equivalent advanced education 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 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.