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Senior Project Manager (Cybersecurity Initiatives)

Job ID : 5867
Category : Enterprise Project Management Office
Brand : Definity
Regular/Temporary : Regular
Fulltime/Parttime : Full Time
Location : Kitchener, Canada

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Definity includes some of Canada’s most long-standing and innovative insurance brands, including Economical Insurance, Sonnet Insurance, Family Insurance Solutions, and Petline Insurance. With strong roots that date back to 1871, we’ve grown to become a digital leader in the insurance industry. We’re proud to help our clients and communities adapt and thrive in a world of constant change.

Our promise to you: It’s better here. Why? Because we CARE, and we provide an employee experience that’s collaborative, ambitious, rewarding, and empowering.

Our ambition is to be one of Canada’s leading and most innovative P&C insurers. Come be a part of our journey, and love what you do.

Starting in September, Definity employees move to a hybrid work model so we can collaborate, build mentoring relationships, and solve complex or cross-functional business opportunities together. Our teams work in whichever environment best supports what they're working on and who they're working with. We're actively reinventing our offices as welcoming workspaces that optimize collaboration and empower leaders to use our space to strengthen team dynamics. Our tools and processes seamlessly connect employees from multiple locations, and our culture encourages respectful engagement and flexibility. Leaders work with their teams to determine the right balance of on-site and remote work that best meets the needs of their team, cross-functional engagement, responsibilities and timelines, plus those of our customers, our broker partners, and the company culture.

Senior Agile Project Manager

The Senior Agile Project Manager will lead large, complex, business critical initiatives encompassing technology and business work steams within the Cybersecurity domain. This role will focus on project delivery across a number of Cybersecurity technology areas including Network, Encryption and others.

What can you expect in this role?

  • The Senior Project Manager understands and is an expert in both Waterfall and Agile methodologies.
  • Responsible for development of an Integrated Project/Sprint Plan and successful delivery of confirmed scope on time and on budget.
  • Effectively serve/engage leadership, Product Owners and Development Teams to assist in the delivery on their respective KPIs
  • Facilitate the Agile process, guide, and mentor teams, remove impediments/blockers or guide the team to remove impediments.
  • Facilitate Agile ceremonies including sprint planning, backlog grooming, daily stand ups, sprint retrospectives, sprint demos and release planning. Lead teams in estimation, sizing, and sprint roadmap exercise.
  • Coordinate project team/POD activities and expectations, including collaboration with all project stakeholders from other Economical areas, internal and external consultants, contractors, vendors, and external regulatory organizations
  • Identify, manage, and monitor risks, assumptions, blockers, impediments, constraints, and internal and cross-track dependencies
  • Adopt established governance model, guiding principles, foundational processes, and procedures, to ensure consistent project delivery practices
  • Work with Finance and project sponsors to track delivery costs and determine benefits realization post implementation
  • Collaborate effectively with cross-functional teams including, Architects, Designers, Developers, Business Analysts, Technical Testers as well as business and IT leadership
  • Collaborate with other Program Leads to ensure Portfolio level interdependencies are understood and managed. Coach teams to effectively build and sustain their own strong collaborative culture.

What do you bring to the role?

  • University Degree or College Diploma in Business, Engineering, Computer Science, Information Systems, or a related discipline; SAFe Agile, CSM, PMP designations are is an asset
  • 5+ years of Project Management and Technical Delivery experience with an emphasis on Cybersecurity, governance, risk management, financial management and stakeholder management
  • Experience leading teams using project management tools and techniques, both Agile and Milestone-based/Waterfall.
  • Able to confidently provide effective written and verbal updates to senior leadership and stakeholders.
  • Experience working with or large system integrator or outsourced IT service providers is an asset
  • Responsible for development of an Integrated Project/Sprint Plan, JIRA roadmaps and successful delivery of confirmed scope on time and on budget.
  • Experience in the Property and Casualty Insurance industry and its related practices and processes is an asset
  • Experience with Jira/Confluence, Microsoft SharePoint, MS Project, or other resource management and tracking tools (e.g., Clarity)
  • A critical thinker, works well under pressure, and perform well in a fast-paced environment
  • Strong written and verbal communication skills; ability to influence and effectively negotiate with stakeholders

We also take potential into consideration. If you don’t have this exact experience, but you know you have what it takes, be sure to give us more insight through your application and cover letter.

Go ahead and expect a lot — you deserve it, and we’ve got it: 

  • Hybrid work schedule for most roles
  • Company share ownership program
  • Pension and savings programs, with company-matched RRSP contributions
  • Paid volunteer days and company matching on charitable donations
  • Educational resources, tuition assistance, and paid time off to study for exams
  • Focus on inclusion with employee groups, support for gender affirmation surgery, access to BIPOC counsellors, access to programs for working parents
  • Wellness and recognition programs
  • Discounts on products and services

Our inclusive work environment welcomes diversity and supports accessibility. If you require accommodation at any time during the recruitment process, please let us know by contacting: [email protected]

Background checks
This role requires successful clearance of a background check (including criminal checks and leadership references).


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