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Senior Learning & Talent Development Partner (Underwriting)

Date: Feb 3, 2023

Location: Toronto, ON, CA, M2P-2B7 Edmonton, AB, CA, T6E-6A8 Calgary, AB, CA, T2R-0E4 Vancouver, British Columbia, CA, V6J-4Y3 Winnipeg, MB, CA, R3C-3P1 Remote - Canada, CA Moncton, New Brunswick, CA, E1E-4R5

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 work from 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 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 senior position on the Talent Development & Programming team is responsible for partnering with strategic business functions to develop targeted learning and talent programming. This role requires the ability to build, develop and lead strong business relationships, translate business needs into talent development programming, and collaborate on a high performing team. This role is critical to the Learning & Talent Development (L&TD) team in supporting Wawanesa’s investment in Talent, and our employee value proposition to attract and retain people and works with the business and other members of the People & Culture Team to support the content and programming needs within targeted areas of the business with the objective of curating, developing, maintaining, and advancing Wawanesa’s suite of Talent Programming. This role works collaboratively with the Learning Operations team.


Job Responsibilities

  • Design, manage, and implement L&TD programming, strategies, and practices - including determining how best to scale programming and build and sustain new programming to support the full employee lifecycle of our people across the organization
  • Translate business needs into strategic development Programs and initiatives and drive them to successful outcomes
  • Obtain the appropriate certification to facilitate development programs, and support business leaders in running courses and workshops 
  • Identify metrics and provide timely, meaningful, and accurate reporting on learning effectiveness, individual and business performance
  • Partner with targeted functional business units to collaborate on an annual calendar of L&TD programming
  • Develop, deliver, and evaluate annual workshops courses and masterclasses as a contributor to the overall enterprise talent programming
  • Drive a culture of continuous learning, knowledge transfer, and growth, where employees “own” their learning and development and there is increased effectiveness and success of Wawanesa’s workforce
  • Apply principles of project management in leading initiatives from identification of impacted audiences and strategic learning needs to the development of targeted programming including the design, development, curation, resourcing, and implementation of quality development programs using innovative learning methodologies and solutions
  • Partner with business to design and develop train-the-trainer programs and provide coaching and guidance to enterprise facilitators on best practices
  • Contribute to the development and maintenance of a governance structure to maintain and ensure all tools, content and materials are current
  • Ensure transparency and visibility of all Programming available across the Enterprise including the regular communication to the business regarding the quarterly and annual Programming calendar
  • Leverage external content and programming available through various agency relationships to complement Wawanesa programming
  • Perform other duties as assigned


  • 5-7 years experience in L&TD Programming with a track record of planning, designing, developing, evaluating and execution/delivery  
  • Minimum 2 years experience in facilitating sessions for medium to large size groups with the ability to engage diverse audiences at all levels
  • Certified Professional in Human Resources (CPHR), Certificate in Adult and Continuing Education (CACE), Certified Training Practitioner (CTP), Certified Training and Development Practitioner (CTDP) or other relevant designations is considered an asset
  • Previous experience developing insurance related programming is considered an asset 
  • Ability to link development programs with talent management and strategic business goals
  • Knowledge of adult learning theories and practices within an organizational context
  • Solid experience translating business needs into learning priorities and providing value for the organization while collaborating, building partnerships and influencing at all levels of an organization
  • Strong business acumen, strategic mindset and problem-solving skills with the ability to work independently to manage, plan and prioritize work and connect the dots
  • Ability to innovate & pivot quickly 
  • Exceptional interpersonal, communication and facilitation skills 
  • Strong technical / technology skills – Microsoft Office Suite
  • Ability and willingness to travel, including the US


Wawanesa is proud to be one of Manitoba's Top Employers for 2022 recognizing that we are an exceptional place to work!

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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