Leader, HR Systems

Job ID : 7396
Category : Human Resources
Brand : Definity
Regular/Temporary : Regular
Fulltime/Parttime : Full Time
Location : Waterloo, Canada
Posting Range : $84,000 - $154,700

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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.

As we continue to leverage our systems to provide a positive and digitally enabled employee experience, the HR Systems team will help define and drive the future of work at Definity.   The goal of the HR systems team is to identify opportunities that delivering innovative solutions that create an efficient and streamlined employee experience while realizing maximum value from deployed HR Systems.

The Leader, HR Systems is accountable for facilitating the development and execution of the HR technology strategy and roadmap in collaboration with key stakeholders and partners.   Upon alignment with the strategy, develops goals for the team to deliver and is actively monitoring progress against the goals and adjusting as necessary. The Leader collaborates with the HR Senior Leadership team to align on priorities and partners with the Technology Solutions organization to plan and deliver.

This role has both an operational and project leadership aspect. Ensuring efficient operation of the system and improving processes and leveraging the system functionality is key day to day. There will also be a need to pivot into project leadership mode when new modules are being implemented.

The Leader, HR Systems is an exceptional problem solve and understands industry trends and best practices. They are curious and can empathize with users and their experience. They are creative and come up with alternatives to solve challenges that face stakeholders. They are always seeking ways to improve the way work is performed.  They maintain the balance between systems’ capabilities and user needs and implement the best solution that both solves the challenge and maintains the integrity of our systems.

What will you do:

Technology Leadership:

  • Identify opportunities for digitization and automation, prioritize and introduce enhancements.
  • In collaboration with key stakeholders within HR and TS, build and execute the strategic HR Technology roadmap that blends support for day-to-day operations with aspirational needs and objectives of HR leadership
  • Collaborate with leaders and ‘people data’ users across the business to find ways to elevate overall enterprise performance and data reliability.
  • Foster a continuous process improvement mindset across the team, leveraging HR technology to ensure optimal utilization of all resources across the HR function
  • Identify trends in the market, products and product roadmaps that have the potential to enhance our employee experience and operating efficiency and factor into the HR Technology Roadmap and service delivery plan.
  • Manage system releases, features, and best practices, proactively review, and recommend new features and functionality.
  • In conjunction with change management and other internal resources, thoughtfully plan deployments and other system changes to improve adoption, manage risk and avoid rework.
  • Establish and implement industry best practices while ensuring work adheres to Definity’s corporate policies and standards.

Team Leadership:

  • Responsible for workload management, goals delivery and communication of deliverables across HR Systems Team.
  • Provide leadership, guidance and coaching to the team to foster the development of the team’s technical expertise and to meet team goals & objectives.
  • Empower and train team members to handle tasks efficiently, fostering a culture of peer-to-peer learning and curiosity.
  • Identify and support training opportunities for the team through knowledge transfer sessions, courses, and projects.
  • Identify and drive opportunities to optimize and streamline processes within teams across HR.
  • In collaboration with Technology Solutions, drive projects and/or programs from inception to implementation including; identifying scope and resources; seeking stakeholder input, identifying key dependencies and providing direction to HR systems team to deliver.. 

Technical Expertise:

  • Be a subject matter expert in multiple functional area of Oracle HCM and HR Systems.
  • In collaboration with our Technology Solutions team, design and configure creative solutions with our Technology Ecosystem
  • Partner with key stakeholders to understand their needs, outline a workplan to achieve the work required and drive the delivery of the work. 
  • Conduct technical lead reviews to ensure proper configuration changes before moving to production.
  • Assist with troubleshooting and provide complex issue resolution, including active ownership of any Severity 1 issues, should they occur.
  • Ensure team’s compliance with change control process and audit requirements on JIRA and Confluence
  • Support and maintain process management documentation for best practices and guidelines


  • Education in Human Resources, HRIS or a related field or equivalent work experience.
  • 10+ years experience in an HR Technology role, preferably using Oracle HCM
  • 8+ years leadership experience managing technology projects and leading people
  • Configuration expertise with at least 2 primary modules of Oracle HCM is required.
  • You must have both functional and technical experience with demonstrated understanding of HR-related tasks, processes and services.   
  • Knowledge of and experience with standard SaaS configuration and deployment approaches and agile project practices is an asset.
  • Commitment to customer service, clear communication, and team collaboration.
  • Strong interpersonal skills and ability to work proactively and collaboratively with cross-functional teams and stakeholders, both within HR and across the organization
  • Effective time management skills to prioritize tasks to ensure timely completion.
  • Ability to maintain discretion and confidentiality with sensitive information.
  • Strong attention to detail to ensure data integrity and high quality.
  • Creative thinker with an innovative, growth mindset.
  • Proven experience with process improvement with the ability to identify and drive changes to processes/work leveraging systems and streamlining work.

Posting Range: $84,000 - $154,700

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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