Remote Data entry Jobs in Regina, SK

At GMS, we've been helping Canadians for more than 75 years to get the health and travel insurance they want and need. The same pioneering spirit that started our story is what drives us to do things differently today. Insurance, honestly, is our promise, and it's what we do at GMS. We care about our customers, our community and each other. As a non-profit organization, we're proud to reinvest our profits into the health of the communities we serve and that have supported us since 1949.

We want our employees to feel good about coming to work and being in a workplace that promotes flexibility, growth and a healthy work-life balance. If you'd like to be part of a team that truly takes care of our customers, our communities, and each other, this could be your chance.

Here's the role

As the Director, IT & Data, you will be responsible for providing the strategic and operational direction for our technology and data functions. You will lead the development and execution of our IT and Digital Transformation strategy, including IT architecture and application development. This role requires the ability to engage in senior level business and technology discussions, provide actionable insight and guidance on delivering customer and business value, integration of end-to-end operations, and balancing of core systems sustainment and the advancement of digital transformation initiatives.

Position Responsibilities

• Develop and execute the company's technology strategy in alignment with business goals.
• Lead and manage the technology teams, including IT, software development, infrastructure and cybersecurity.
• Identify and implement innovative technology solutions to improve products, services and internal processes.
• Manage major technology and business projects, including budgeting, scheduling and resource allocation.
• Establish and manage relationships and contracts with third party vendors and partners.
• Ensure the company's technology systems are secure and compliant with industry standards and regulations.
• Translate and simplify complex business and technical concepts into clear, simple, and actionable information for both technical and non-technical teams.
• Promote and champion AI initiatives
• Oversee the organization's architecture and provide project oversight for the technical components
• Recruit, mentor, and develop the technology team, fostering a culture of continuous learning.
• Collaborate closely with other departments to ensure technology solutions align with overall business needs.
• Proactively Identify potential technology risks and implement mitigation strategies to safeguard business continuity.

Competencies

• Customer Centric: Demonstrates a clear understanding of who our customers are - whether internal or external - and considers the customer perspective in all actions and decisions to create value, strengthen trust, and contribute to a positive customer experience.
• Innovation & Technology: Leverages emerging technologies and innovation to transform operations and business models, embedding them into strategy and culture to secure long-term organizational success.
• People Leadership & Talent Development: Leads with vision, sets people strategy and develops talent to drive performance and results. Aligns team direction with organizational strategy, cultivates high performance, and builds future leaders through coaching, feedback, and intentional development. Fosters a purpose-driven culture of ownership and empowerment, focused on delivering meaningful results.
• Impact and Influence: Inspires a shared purpose and fosters commitment in alignment to the organization's mission and strategic goals. Connects perspectives and insights from internal and external sources to inform and influence decisions. Builds credibility and partners with key stakeholders to help shape culture, direction, and solutions around a clear, shared vision. Drives innovative thinking and challenges others to analyze assumptions and problems from multiple angles.
• Strategic Thinking & Vision: Translates vision into clear, actionable plans that drive strategic objectives and inspire forward momentum. Looks forward to anticipate future impacts and risks to shape strategy and guide decisions, ensuring alignment with the organization's vision and long-term goals.
• Communication: Communicates complex or sensitive ideas with influence and clarity; fosters shared understanding across diverse stakeholders. Takes in sources of information from various stakeholders and business perspectives and translates information into a consumable message.
• Results Orientation: Drives others to deliver high-impact, outcome-focused results - even in high-pressure or challenging situations. Sets clear expectations, keeps efforts aligned with priorities and maintains momentum through accountability. Removes obstacles, remains agile and ensures results meet or exceed expectations.

Education & Experience

• Undergraduate or master's degree in a technology or business-related discipline is required
• 8+ years of experience leading technology teams focused on digital transformation
• A deep understanding of the Digital Ecosystem, Digital Innovation, and Advanced Analytics
• Insurance industry knowledge considered an asset
• A genuine passion for leveraging technology to achieve excellence in customer experience

When you become a GMSer, you can expect:

• Competitive salary, bonus opportunities and a comprehensive benefit package.
• Personal and professional development initiatives.
• Social events, volunteer opportunities, and a whole lot of fun.
• Free coffee - yes, really! And if tea is more of your vibe, we've got that covered too!

Are we a fit?

If you think so, please apply by Wednesday March 25, 2026. We'd love to reach out to everyone who applies, but we just don't have enough hands! If you're selected for an interview, we'll be in touch. If not, please consider us again in the future.