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Senior Leadership Development Specialist

March 14 2021
Industries Bank, Insurance, Financial services
Categories HR, Training, Training - Development - Improvement
Toronto, ON

Wawanesa Mutual Insurance is one of the largest property and casualty insurers in Canada with $3 billion in annual revenues and assets of more than $9 billion. Wawanesa Mutual, founded in 1896 with executive offices in Winnipeg, is the parent company of Wawanesa General, which offers property and casualty insurance in California and Oregon, and Wawanesa Life, which distributes life insurance products and services throughout Canada. With over 3,500 employees, Wawanesa proudly serves over 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, advancement on a growing team.

Job Overview

Working under minimal supervision, this job contributes to Wawanesa’s success by leading, designing, developing, coordinating and conducting comprehensive leadership development programs using a blend of learning methodologies in support of Wawanesa’s strategic initiatives and enterprise wide development programs.

Job Responsibilities

  • Lead the design, development and implementation of leadership development programs for Wawanesa, including the delivery/facilitation of the program (workshops, courses, etc.):
  • Conduct organization wide needs assessment and identify learning and development gaps that need to be addressed
  • Design, launch and manage development programs – design multi-level blended-learning programs that support Wawanesa business strategy and development needs for all roles across the organization
  • Engage key stakeholders in the program design and focus – manage launch, metrics and modifications needed to address changing needs over time
  • Partner with internal stakeholders and liaise with subject matter experts regarding instructional design
  • Report progress against development timeline targets – assessment of instructional effectiveness, impact of training and continuous improvement efforts for programs
  • Build development programs linked to achieving Wawanesa’s talent initiatives and goals
  • Engage with business leaders on key strategic priorities, Human Resources teams to provide the appropriate supporting learning and development programs
  • Provide input to the Learning & Development (L&D) Strategy and map out training plans, design and develop training programs (outsourced or in-house)
  • Develop train-the-trainer programs and provide train-the-trainer sessions for internal subject matter experts
  • Obtain the appropriate certification and facilitate leadership development programs (courses, workshops) as required
  • Choose appropriate training methods (simulations, mentoring, on the job training, professional development classes etc.)
  • Use accepted education principles and track new training methods and techniques
  • Support implementation and delivery/facilitation of in person, virtual, mobile training
  • Market available training opportunities to employees and leadership
  • Management of the learning management system and/or training database, as required
  • Ensures adherence to the training and development policy when developing programs in projects or working with departments
  • Stay current on research and monitor best practices in learning and leadership development and implement as appropriate for the organization
  • Work with vendors to ensure they provide highest quality of service
  • Conduct and manage program evaluations to report on program results, metrics and ROIs
  • Provide program related administration and managing program logistics to ensure training requirements are met. This includes:
  • Emailing training pre-work and class reminders to applicable participants
  • Shipping training materials, managing catering, coordinating training vendors and filing contracts
  • Enrolling participants, scheduling courses, maintaining a training calendar and booking training rooms
  • Perform other duties as assigned


  • Five to seven years’ experience planning, designing, developing, coordinating and delivering learning and development programs, with at least two years in an eLearning environment
  • Minimum 2 years’ experience in facilitating learning and development training/learning sessions for medium to large size groups
  • Expertise and experience in building/managing leadership development programs across the organization
  • Completion of post-secondary degree/certificate or equivalent experience
  • Expertise and experience in building development programs for multiple levels within and across the organization
  • Knowledge and understanding of processes to ensure linkage of development programs with talent management and development programs including identifying experiential learning, action learning experiences, peer coaching, mentoring and other program needs that support career growth and development for employees and leaders
  • Experience in applying action learning and adult learning principles, E-learning knowledge and application in development programs
  • Excellent facilitation skills; ability to engage diverse audiences and at all levels
  • Excellent analytical and problem solving skills, with the ability to conduct detailed analysis of information, and to create and deliver best solutions
  • Excellent communication, negotiation and presentation skills, with the ability to communicate at the right level for the intended audience using various methods
  • Excellent planning and organizing skills, with the proven ability to prioritize, handle multiple assignments, work accurately within tight timelines and interact collaboratively in a team environment
  • Excellent attention to detail with the ability to develop relevant information and potential impacts
  • Ability to deliver results in a fast-paced environment
  • Proficient with Microsoft Office Suite
  • Certificate in Adult Education (CAE, CACE) is considered an asset
  • Knowledge and experience in the insurance industry is considered an asset
  • Ability and willingness to travel as required

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. We’re also proud to give our employees in Canada the flexibility to choose how and where they want to work. Options in most roles include work from the office, from home, or a hybrid mix of time spent at both.

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, color, 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. network