Agile Team Coach, Direct Venture

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Date: Oct 9, 2026

Location: North York - Toronto, ON (Hybr, CA Montreal, QC (Hybrid), CA Winnipeg, MB (Hybrid), CA Kitchener, ON (Hybrid), CA

Company: Wawanesa Insurance

Job ID: 10403 


Employment Type: New Role

 

Work Environment: We offer a hybrid work environment that offers flexibility to our employees in balancing in-office (2 days per week OR 15 hours per week in a Wawanesa office) and remote work. You may work from any of the following locations: Winnipeg, MB; Wawanesa, MB; Toronto (North York), ON; Kitchener, ON; Montreal, QC.

 

Working Business Language: English. This role is considered a head-office role and will be required to communicate with internal stakeholders across Canada where the primary business language utilized is 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. The salary offered is estimated to be within the following range: $110,000 - $135,000. Candidates with salary expectations outside of the range are still encouraged to apply. 

 

About The Wawanesa Mutual Insurance Company
Founded in 1896, The Wawanesa Mutual Insurance Company is one of Canada’s largest mutual insurers, fully owned by its more than 1.8 million members. Headquartered in Winnipeg, Wawanesa is the parent company of WSI™, a specialty insurer delivering tailored solutions built around unique needs; Wawanesa Life, a provider of life insurance products; and Western Financial Group, a leading national distributor of personal and commercial insurance.

Wawanesa is committed to helping communities thrive in a changing world. The company invests more than $4 million annually in charitable initiatives, including $2.5 million each year to support people and communities on the front lines of climate change. Learn more at wawanesa.com.

 

We are currently seeking dedicated, driven, and enthusiastic individuals who thrive in a dynamic environment, embrace change, and are eager to gain diverse experience while advancing their careers as part of a growing team.

 

Job Overview

​​The Agile Team Coach, Direct Venture enables effective Agile delivery across Direct-to-Member (D2M) workstreams by improving team flow, transparency, maturity, and continuous improvement. The role establishes consistent working agreements, fit-for-purpose Scrum/Kanban practices, healthy backlogs, meaningful metrics, and early visibility of risks and dependencies.​ 

 

Reporting to the Director, Innovation Execution, the role partners with Product Owners, Business Analysts, delivery teams, technology, PMO/EPMO, and business stakeholders to help teams deliver and learn at pace. 

Job Responsibilities

  • Facilitate Scrum events and Agile rhythms that clarify goals, decisions, ownership, and improvement across D2M workstreams. 
  • Coach teams on working agreements, team norms, Definition of Ready/Done, and practical delivery guardrails. 
  • Identify, remove, and escalate impediments; surface readiness gaps, risks, dependencies, blockers, external needs, and decisions early. 
  • Build Agile capability through practical coaching, workshops, examples, and repeatable practices tailored to team maturity. 
  • Improve backlog health through refinement, estimation, story slicing, acceptance criteria, dependency management, Sprint Goals, and Test & Learn. 
  • Promote shared ownership, outcome focus, and proactive planning while preserving Product Owner accountability for priority and value. 
  • Partner across product, delivery, technology, and PMO/EPMO to provide lightweight views of progress, learning, risks, dependencies, and decisions. 
  • Advance Jira, Confluence, dashboards, roadmaps, workflows, and reporting to improve transparency, consistency, actionability, and scale while reducing manual effort. 
  • Support lightweight governance and operating rhythms; define measures including Sprint Goal achievement, readiness, blockers, flow, quality, confidence, risk, dependencies, and learning. 
  • Help teams reserve capacity for learning, tooling, automation, technical debt, retrospective actions, and enablement. 
  • Apply Wawanesa Technology Delivery Model guidance pragmatically and create reusable playbooks, templates, checklists, coaching, and onboarding materials. 
  • Use retrospectives, team health indicators, delivery data, and stakeholder feedback to implement focused improvements. 
  • Foster psychological safety, transparency, disciplined experimentation, evidence-based decisions, clear ownership, constructive challenge, and rapid learning. 
  • Perform other duties as assigned. 

Qualifications

  • 7+ years of relevant experience in Agile, technology, transformation, product, or complex cross-functional delivery, including 5+ years as a Scrum Master, Senior Scrum Master, Agile Team Coach, Agile Delivery Lead, or similar. 
  • Experience supporting multiple teams or workstreams with varying Agile maturity; regulated enterprise, insurance, financial services, or fintech experience strongly preferred. 
  • Post-secondary education in business, technology, engineering, information systems, or a related field, or equivalent experience, preferred. 
  • Scrum/Agile certification such as CSM, PSM I/II, A-CSM, CSP-SM, PMI-ACP, SAFe Scrum Master, SAFe Agilist, or equivalent, preferred. Kanban, Agile Coaching, facilitation, change management, Lean, product operating models, P&C/CIP, or regulated financial services experience is an asset. 
  • Strong knowledge of Scrum, Kanban, Agile principles, iterative delivery, backlog readiness, Sprint Goals, flow metrics, and continuous improvement. 
  • Advanced facilitation and coaching skills across workshops, retrospectives, planning, refinement, dependency management, and difficult conversations. 
  • Ability to influence without authority across product, technology, business, PMO/EPMO, and senior stakeholders, and translate delivery complexity into leadership-ready insights. 
  • Sound judgment balancing speed, governance, quality, and learning in an early-stage venture. 
  • Demonstrates servant leadership, systems thinking, delivery discipline, curiosity, adaptability, stakeholder partnership, customer focus, and courage to surface risks and challenge assumptions constructively. 

 

#LI-AF1 #LI-hybrid #ScrumMaster


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.