Director, Technology Strategy and Execution

Job ID : 7496
Category : Technology Solutions
Brand : Definity
Regular/Temporary : Regular
Fulltime/Parttime : Full Time
Location : Toronto, Canada
Posting Range : $97,000 - $178,800

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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.

Director, TS Strategy Execution is a high visibility Senior Leader role working with internal and external executive leadership in formulation and delivery of Technology Strategy.  Report directly to the AVP, TS Strategy, and Communication this individual executes large-scale strategic initiatives and drives meaningful results leveraging strategic partnerships and internal teams to drive operational effectiveness and innovation across technology. This role develops and executes distinctive Technology strategies that achieve competitive advantages and translates broad strategies into specific objectives and action plans ensuring our Technology teams are optimized and enabling achievement of key business objectives. 

What can you expect in this role?  

Technology Strategy Execution 

  • Develop and implement new operating model across TS, and lead multi-year execution of a large scale strategic initiative to drive operational effectiveness 
  • Independently complete analysis of technology options and provide data supported recommendations aligning with TS and Business strategy  
  • Lead center of excellence for metrics to monitor the progress of strategic plans engaging stakeholders as required to ensure strategic objectives are met  
  • Contribute to the development of the TS strategic initiatives by leveraging unique problem-solving methods and frameworks 
  • Lead the development of materials and presentations that will shape decision-making by Executive Leadership Team (ELT) and Board of Directors (BOD) 

Technology Strategy Development:  

  • Lead GenAI technology strategy development and support execution for one of the key partnerships 
  • Research and promote understanding of relevant external and internal technology trends and contexts, providing recommendations and options 
  • Guide and manage external advisors, vendors, and consultants 
  • Establish and maintain effective working relationships with key stakeholders internally and externally, including the CTO and TS Senior Leadership Team 
  • Facilitate working sessions with a broad range of functional stakeholders  

What do you bring to the role? 

  • 10+ years of technology strategy experience gained at a top-tier management consulting firm  
  • Management consulting experience is a must 
  • Experience in key technology domains such as Cloud, DevOps, and Tech Operations is a big plus 
  • Experience in leading and managing large scale transformations or strategic initiatives which includes working with external partners 
  • Proven track record to lead multiple teams to be successful and achieve their goals 
  • Proven ability to learn quickly and gain expertise in new functional areas 
  • Acute attention to detail and strong commitment to producing excellent work products 
  • Experience in evaluating new opportunities and the ability to connect technical concepts to business concepts 
  • Strong business and technology acumen, with demonstrated aptitude for strategic, analytical, and critical thinking 
  • Able to lead and drive discussions with executives from different parts of the company 
  • Ability to perform under pressure, meets deadlines and handles multiple, and sometimes conflicting priorities 
  • Exceptional verbal and written communication skills across a range of contexts, with the ability to explain detailed and technical information in a simple and creative manner  
  • Team player with demonstrated ability to collaborate with others to achieve results 
  • Strong relationship building skills with the ability to build rapport with a wide variety of people across the organization 
  • A high degree of personal ethics, integrity, and responsibility with an ability to deal with sensitive issues and safeguard confidential information 
  • Expert proficiency in Microsoft PowerPoint and Excel is required 
  • P&C insurance industry experience is desired but not necessary 

Salary range: $97,000 - $178,800

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).


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