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Technology Delivery Manager

Job ID : 5755
Category : Technology Solutions
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.

As a Technology Delivery Manager, you will be responsible for leading the end-to-end delivery of technology solutions (TS) led initiatives. This is crucial role for the TS delivery organization as we move towards platform and application- based delivery. We are looking for delivery leads with the right expertise and flexible experience in navigating complex, technology-driven implementations, leveraging both traditional and iterative / Agile delivery methodologies. On a day-to-day basis you will work closely with senior technology and business stakeholders to drive delivery and coordination activities across multiple cross-functional project teams – your practical experience will be key to enabling these teams, while also growing our internal delivery capabilities for future transformations. 

While not limited to a single functional area, we are currently seeking delivery leads to support Definity’s recent partnership with Google Cloud


  • Own and lead project delivery across multiple types of technology platform initiatives
  • Partner with senior stakeholders to maintain a pipeline of business and technology use cases that can potentially use capabilities found on Google Cloud Platform
  • Provide partnership governance support to Corporate Strategy and Technology leaders; this will include organizing periodic leadership and steering committee forums
  • Where required, lead mobilization, planning, and execution of business use cases with Definity (both business and technology) and Google teams
  • Lead a team of business analysts, systems analysts, and architects to develop use case planning deliverables in alignment with Enterprise Architecture strategy
  • Interlock with Google-enabled use cases executed through the project Portfolio to ensure connectivity and alignment with the overall partnership governance
  • When required, provide planning input and collateral for annual Portfolio and Business planning
  • Establish and maintain practical project governance practices and forums, ensuring that team impediments and blockers are resolved in a timely manner, while also keeping executive stakeholder informed
  • Manage and drive resolution / mitigation for known issues and risks
  • Support coordination with TS Architects to develop high-level solution designs and TRB/ARB approvals
  • Provide supporting data / insight to TS Leaders and Portfolio Managers where necessary
  • Build strong working relationships within the TS organization to ensure optimal performance and ensure what we deliver meets business and technology objectives, results, and benefits
  • Use appropriate fact-based metrics / assumptions to determine and convey impact on budget, time, and risk.
  • Close project delivery with proper hand-over to operation / support teams
  • Report into Executive leadership regularly to provide status updates
  • Support TS platform leaders with informing portfolio plans and strategy
  • Support ad-hoc project analysis and reporting
  • Translate sprint plans in JIRA to timelines and commitments for reporting to executives.
  • Support vendor RFP and RFI activities where necessary


  • Degree in business, computer science or a related discipline is preferred
  • 5+ years of leading and implementing technology initiatives in financial services
  • 3+ years of applying Agile and Waterfall delivery practices for building modern and emerging platform capabilities (e.g., Big Data, Analytics, CRM, Contact Centre, Cloud Migration, Guidewire)
  • Experience in delivering IT initiatives through Agile / Iterative and Waterfall delivery methodologies
  • Experience in leveraging DevOps philosophy and tooling to streamline development, testing, and deployment activities
  • Experience in adapting Agile practices to implementing back-end, data-driven solutions / platforms with multiple cross-team dependencies
  • Experience in successfully delivering initiatives with matrix structured teams consisting of dedicated and shared resources
  • Experience in managing multiple cross-functional teams (BA, Dev, Testing, Security, Compliance, Infrastructure)
  • Experience in delivering applications on GCP, AWS, and / or Azure is an asset
  • Experience in delivering IT solutions in insurance or banking industries is an asset
  • Demonstrate an ability to lead and manage a team in a busy and changing environment while fostering positive performance and engagement
  • Models solid leadership skills with the ability to coach, develop, motivate, and retain staff. 
  • Strong analytical, time management and organizational skills
  • Proactively communicates information in a clear and positive manner. Layering excellent decision-making skills with a natural aptitude for observation
  • Exceptional organizational and time-management skills to multi-task and effectively manage competing and changing priorities
  • Demonstration of a can-do attitude, with ability to effectively navigate through challenges
  • Ability to work effectively in a matrix and shared services organization
  • Relevant industry-related certifications e.g: PMP, Six Sigma, CSM, SAFe
  • Scrum Master skill set would be an asset
  • Practical knowledge of project management techniques, tools, methodologies

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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