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Technology Delivery Manager

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Job ID : 5683
Category : Technology Solutions
Brand : Definity
Regular/Temporary : Regular
Fulltime/Parttime : Full Time
Location : Toronto, 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.

LOVE WHAT YOU DO

Work is a big part of our lives, so it makes sense to choose a company that offers truly rewarding work. At Economical Insurance®, your contributions, creativity, and energy won’t go to waste. Our passionate culture and pioneering mentality infuse everything we do, which is why our one-million-plus policyholders know we’ll protect their homes, businesses, farms, cars, and pets like they’re our own.


We’re not afraid to see how far we can push the envelope to make insurance better. Our family of companies includes Sonnet, the only Canadian home and auto insurer offering a fully online buying experience, and Petline, the largest Canadian pet insurance company. We’re also preparing to become a publicly traded company, a once-in-a-lifetime career opportunity for everyone who joins our team.

If you’re looking for a company that takes care of its people — and its customers — and has a track record of doing big things, get ready to love it here.

The Delivery Manager will be accountable for overseeing the delivery of strategic technology projects / program in the Guidewire Policy Center, Billing Center and ClaimCenter (PC, BC, CC).  This function will lead one or more agile pods, and provide overall leadership of the collective efforts across the TS organization required to execute on the projects.

You will work closely with senior technology stakeholders to drive day-to-day delivery activities, manage multiple project teams, oversee project and portfolio financials, and support communications with TS and business teams.

This role will report into AVP, Technology Services


What can you expect in this role?

  • Own and lead the end-to-end delivery of Guidewire initiatives, including project mobilization, planning, and resourcing with internal and external partners
  • Establish Guidewire intake and governance forums and practices, ensuring appropriate oversight committees are in place and meet regularly
  • Manage and drive resolution/mitigation for known issues and risks
  • Partner with TS Architects to coordinate high-level solution designs and TRB approvals
  • Manage overall Guidewire portfolio and project financials including partnering with TS leadership and Finance partners to track costs associated with Integration activities.
  • Build strong working relationships within the TS organization to ensure optimal performance and ensure what we deliver meets key performance indicators and stated benefits
  • Use appropriate fact-based metrics/assumptions to determine and convey the impact on the budget, time and risk.
  • Work and manage all aspects of Change and Release management related to the project/pod deliverables
  • Leveraging disciplined agile practices to develop and execute an end to end delivery plan
  • Managing program risks & issues; proactively driving risk mitigation and issue resolution
  • Manage the project pipeline and sequencing with input from the business/product teams as well as various technology partners within the bank
  • Report into Executive leadership regularly to provide status updates
  • Support vendor RFP and RFI activities where necessary


What do you bring to the role?

  • Degree in business, computer science or a related discipline is preferred
  • 4+ years of leading and implementing IT infrastructure, Cloud, and Guidewire Initiatives.
  • Technical and development experience working with the Guidewire platform
  • Experience in delivering IT initiatives through Agile and / or Iterative delivery methodologies
  • Experience in successfully delivering initiatives with shared resources
  • Experience in establishing, actively managing, and monitoring an IT project portfolio
  • Experience in managing multiple cross-functional teams (BA, Dev, Security, Compliance, Infrastructure)
  • Experience in delivering IT solutions in insurance or banking industries is an asset
  • Experience in managing a portfolio of initiatives that requires a varying level of delivery support / leadership
  • 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
  • Ability to work effectively in a matrix or shared services organization
  • Relevant industry-related certifications e.g: PMP, Six Sigma, CSM, SAFe
  • Scrum Master certification would be an asset
  • Practical knowledge of project management techniques, tools, methodologies
  • This role can be located in Toronto or Kitchener

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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