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Technical Project Manager

Date: Aug 11, 2022

Location: Toronto, ON, CA, M2P-2B7 Moncton, New Brunswick, CA, E1E-4R5 Edmonton, AB, CA, T6E-6A8 Kitchener, ON, CA, N2G-1H6 Ottawa, ON, CA, K2E-7W5 Calgary, AB, CA, T2R-0E4 Regina, SK, CA, S4S-6X3 Saskatoon, SK, CA, S7H-0W5 Remote - Canada, CA Winnipeg, MB, CA, R3C-3P1 Vancouver, British Columbia, CA, V6J-4Y3

Company: Wawanesa Insurance


We’re proud to give our employees the flexibility to choose how and where they want to work. In this role, you can decide whether your preference is to work from home (remote), work from the office or a hybrid of time spent at both. You may live in and work in any of the following locations: British Columbia, Alberta, Saskatchewan, Manitoba, Ontario, New Brunswick, Nova Scotia, Prince Edward Island, Newfoundland & Labrador and/or the Yukon.  


The Wawanesa Mutual Insurance Company, founded in 1896, is Canada’s largest mutual insurer, with $3.9 billion in annual revenue and assets of $10.5 billion. Wawanesa Mutual, with executive offices in Winnipeg, is the parent company of Wawanesa General, which offers property and casualty insurance in California and Oregon; Wawanesa Life, which provides life insurance products and services throughout Canada; and Western Financial Group, which distributes personal and business insurance across Western Canada. With more than 5,700 employees, Wawanesa proudly serves more than two million policyholders in Canada and the United States. Wawanesa is thrilled to be named one of Canada’s Best Employers by Forbes for 2022. This certification recognizes us as a leading employer and reinforces that we’re a company that values our people for who they are and the work they do to support our customers, communities, and brokers. Wawanesa is also a Manitoba Top Employer for 2022 recognizing that we are an exceptional place to work. Wawanesa actively gives back to organizations that strengthen communities where it operates, donating well above internationally recognized benchmarks for excellence in corporate philanthropy.

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 Technical Project Manager / Information Services (IS) Supervisor leadership position will be part of Digital Broker Experiences team and will help drive Wawanesa’s success in maintaining, supporting, and enhancing our Broker experiences applications.
This job will be part of the overall Digital Delivery department which focuses on developing and enhancing Wawanesa’s broker facing digital solutions using industry leading technologies and frameworks. This includes building the ecosystem using a broker centric design approach with a strong focus on enhancing the user experience for our brokers in Canada. 
We are looking for a highly motivated and organized self-starter to lead the team in building the next generation of insurance experience.
Job Responsibilities

  • Lead, influence and mentor a team of developers and solution analysts (direct reports) to ensure work environment is respectful, challenging, and rewarding, ensuring employees are utilizing their full potential while contributing to achieving organization goals.
  • Create and manage development delivery plans for continuous delivery cycle, and work with business stakeholders to prioritize deliverables based on expected outcomes and capacity
  • Develop and deliver project status updates, operational reports and presentations to various stakeholders
  • Manage application development team activities to ensure successful completion of work assignments
  • Manage and maintain applications, following IS and industry best practices and operational standards and SLAs
  • Constantly improve their own and their teams' skills and processes through lessons-learned reviews and leveraging industry knowledge.
  • Appropriately assess risk when business decisions are made, and help resolve and escalate risks as necessary


  • Completion of post-secondary degree/certificate or equivalent experience.
  • 3 years’ experience performing senior Information Technology / Information Services role related to Application Delivery.
  • Experience with relevant analysis, design, system development, maintenance tools and technology.
  • Knowledge and practical experience using agile methodologies and standards for software development life cycle.
  • Strong communication skills, with the ability to communicate in a clear and concise manner with style fitting for the audience and message.
  • Strong planning and organizing skills, with the ability to develop and implement plans by prioritizing and multi-tasking.
  • Good leadership skills, with the ability to facilitate high team morale by encouraging and coaching team members.
  • Good decision-making skills, with the ability to direct team members to achieve goals through clear instruction.
  • Experience with Salesforce is considered an asset.
  • Experience in UI/UX and CX practices like design thinking is considered an asset.
  • Experience in programming concepts is considered an asset.
  • CSM, PMP certifications is considered an asset.
  • Knowledge and experience in Property & Casualty industry is considered an asset.


Wawanesa provides its employees with a respectful, challenging and rewarding environment where they can maximize their potential while contributing to the company’s goals. Our full-time permanent employees are provided with highly competitive compensation packages (salaries, generous vacation allowance, leave top up, annual bonus plan, premium free benefits and a pension plan). Wawanesa provides a stable environment for its employees in today’s challenging markets. 

Wawanesa is an equal opportunity employer and is committed to fostering a diverse workforce that is equitable and inclusive for all. Wawanesa provides equal employment opportunity to all employees and applicants without regard to an individual’s protected status: race/ethnicity, colour, religion, creed, sex or gender, sexual orientation, gender identity or expression, family or marital status, pregnancy/childbirth or related conditions, national origin, disability, military or veteran status, or any other protected status. Accommodations are available upon request throughout all aspects of the selection process. Candidates requiring accommodations may contact, in confidence,

If you are interested in this exciting, challenging position with Wawanesa, apply today with your Resume.

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