AVP, Digital Technology

Job ID : 6787
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.

Definity offers 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. Leaders partner with their teams to find the right balance of on-site and remote work that best meets the needs of their teams, colleagues, brokers and customers, while ensuring collaboration, teamwork and accountability for goals.


The AVP - Digital Platforms is accountable for the strategy, design, and implementation of business capabilities enabled through Definity’s digital platform ecosystem.  Working with technology and business senior leadership on strategy development, solution design, policy development, process enhancements, and operational controls building world-class digital experiences. The AVP will work with Senior stakeholders across the organization to develop robust business cases for transformational initiatives and manage the digital programs to ensure strategic objectives are met.   


What can you expect in this role?  

  • Working with passionate business and technology leaders in the definition and execution of an industry-leading digital technology strategy  
  • Collaborate with the business and technology leadership to ensure alignment of priorities, approaches, and activities across teams to effectively deliver on overall  team objectives  
  • Develop, coach, and manage the performance of direct reports, ensuring the achievement of business, functional, and individual goals  

TS Transformation / Performance Management  

  • Manage a portfolio of technology currency and modernization initiatives  
  • Maintain and execute the capability building / continuous improvement within delivery team aligned with industry best practice   
  • Build and manage technology reporting and the internal/external stakeholder engagement and communications plan, and communications calendar  
  • Design / identify and report optimal success metrics to measure to evaluate the performance of all TS functions/teams  
  • Actively manage and monitor progress against the plan, adjusting priorities as required, and regularly communicating progress to key stakeholders 

Strategic Partner  

  • Partner with internal business clients to develop a business-backed Digital strategy  
  • Ability to build meaningful relationships and engage stakeholders across the organization  


What do you bring to the role?  

  • University Degree in business, computer science, information systems or a related discipline is preferred  
  • 10+ years of digital design and development experience including 7+ years in a leadership role in software delivery/engineering role in the insurance or financial services industry  
  • Demonstrated experience implementing the production-level solution in a medium to large enterprise  
  • Expert written & verbal communication skills – able to translate complex, technical topics into clear messaging - effectively communicate/explain technology and its implications to business and technology executives  
  • Strong knowledge of contracting, negotiating, portfolio management, process management, technology trends, and digital technologies  
  • Understanding and the ability to teach good design and architecture principles and non-functional requirements 
  • Demonstrated advanced technical expertise in the following technologies  


Must haves:  

  • Substantive work experience leading large scale delivery initiatives
  • Executive presence and communication skills  
  • Ability to synthesize information, establishing sound inferences when information is incomplete, and draw testable conclusions\recommendations  
  • Experience working with cloud hyperscalers in delivery and maintenance of PaaS applications  
  • Experience working with SaaS based customer engagement platforms (I.e. CRM, CCaS, WFM)  
  • Experience in the application of commercialized AI\machine learning tools that advance the efficiency and quality of customer engagement  
  • Ability to design and interpret digital application design and services through contemporary patterns and frameworks Other expertise which will be an asset:  
  • Experience working in optimized DevOps environments and supporting the transition to a DevOps, SRE, CI\CD capable organization  
  • In-depth understanding of iterative\agile behaviors and ways of working congruent with development and build of application code\configuration  
  • Working knowledge of commercialized and open source AI\ML vendors and tooling, supporting infrastructure and MLOps concepts  

Leadership, Partnership, and Influence  

  • Highly collaborative individual with the ability to build and maintain effective relationships with many business partners, stakeholders vendors, and TS teams to achieve results  
  • Skilled at defining, motivating, and driving change at executive levels and across the broader community of stakeholders  
  • Believes in a non-hierarchical culture of collaboration, transparency, safety, and trust   
  • Skilled influencer and negotiator  


  • Demonstrated outcomes delivering on the Digital technology platforms  
  • Experience with leading a change management agenda in large scale organizations, with proven ability to influence at all levels of the organization  
  • Passionate about technology and excited about the impact of emerging / disruptive technologies and the impact on business outcomes  

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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