Sr Tech Lead, Guidewire

Definity is the parent company to some of Canada’s most long-standing and innovative insurance brands, including Economical Insurance, Sonnet Insurance, Family Insurance Solutions, and Petline Insurance. Our ambition is to be one of Canada’s leading and most innovative property and casualty insurers. We can’t do that without our people, so we embrace and encourage a culture that’s collaborative, ambitious, rewarding, and empowering.

We offer a flexible, hybrid work experience where employees work from the office and virtually depending on the type of work they are doing and who they are working with. Bring your true self and be a part of our journey. It’s better here.

The Senior Technology Lead will be accountable for overseeing the delivery of strategic technology projects / program within Product, Underwriting and Rating Value Stream (Guidewire, Third Party Vendor and API Integrations) for Personal Insurance. This function will provide overall leadership of the collective efforts across the TS organization required to execute on the Business Goals and Projects.

You will work closely with senior Business and Technology stakeholders to drive day-to-day delivery activities, manage multiple project teams, drive technical vision and support communications with TS and business teams.

This role will report into AVP, Personal Insurance.

What can you expect in this role?

• Own and align engineering goals with the broader organizational strategy and to be able to foresee challenges and opportunities
• Work with vendors and partners to understand upcoming technology features and capabilities and incorporate them into technology roadmap
• High level of self-awareness, empathy and interpersonal skills to manage team dynamics and boost employee morale
• Ability to lead diverse teams, fostering a culture of collaboration and innovation and mentoring junior to mid-level technology talent.
• Manage and maintain delivery best practices, ensuring appropriate oversight committees are in place and meet regularly
• Deep understanding of Guidewire technology, development best practices and personal insurance knowledge
• Manage and drive resolution / mitigation for known issues and risks
• Partner with TS Architects to coordinate high-level solution designs and Architecture Board approvals
• Capacity to make informed, data-driven decisions quickly, often balancing multiple competing priorities and constraints.
• 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 impact on 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 on an end-to-end delivery plan
• Expertise in managing large-scale projects, including planning, risk management and ensuring on-time delivery
• Manage the project pipeline and sequencing with input from the business/product teams as well as various technology partners within the organization
• 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
• 12+ Years of hands-on Guidewire experience with deep technical understanding across Policy, Billing and Claims
• 5+ years of leadership experience driving end-to-end implementations of Personal Insurance, Cloud, and Guidewire transformation Initiatives at scale.
• Technical and development experience working with Guidewire, API and Reporting platforms.
• Experience in delivering IT initiatives through Agile and / or Iterative delivery methodologies
• A track record of building strong cross-functional (BA, Dev, Security, Compliance, Infrastructure) partnerships, aligning technological efforts with product, design and business stakeholders to deliver impact on scale
• Experience in successfully delivering initiatives with shared resources
• Experience in a leadership style grounded in openness and clarity, ensuring team members understand the “why” behind decisions and feel connected to the org strategy.
• Models’ solid leadership skills with the ability to coach, develop, motivate, and retain staff.
• 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
• 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
• Must be Guidewire ACE Certified preferably in Policy Center or Integration
  
  
  

Role ID - 126

Interested in this role, but don't meet every requirement? We encourage you to apply! We know from experience that a candidate doesn't need 100% of the qualifications listed to bring incredible value to our team. We're actively seeking diverse backgrounds and perspectives to help us make insurance better. At Definity, inclusion, diversity, and equity aren't just "nice to have" — they're essential to our success.

What's in it for you?

• 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
  
  
  

Actual salary for the role may vary depending on work location of the successful candidate and other factors including but not limited to, skills, education, experience, working conditions and the local labour market.  In addition to base pay, eligible employees may participate in various incentive plans which are paid out at the discretion of the company and subject to individual and company performance.

Go ahead and expect a lot — you deserve it.

It's better here — but don't take our word for it. Definity was named by Great Place to Work as one of the Best Workplaces in Canada for women, for youth, and for inclusion.

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 background checks (including criminal checks and leadership references).