Executive Project Manager Jobs in Saskatchewan (NOW HIRING)

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

Based in Regina, Saskatchewan, The Vice President, Data and Technology is a member of the Executive Leadership Team and is responsible for leading the organization's technology strategy and delivery, including data and AI, digital modernization initiatives, and program management office (PMO) portfolios. This role oversees enterprise technology operations, cloud platform integrations, analytics, infrastructure and cybersecurity. As a member of the Executive Leadership Team, the Vice President drives innovation, manages technology investments, vendor partnerships, enterprise risk, and ensures technology solutions deliver operational excellence. This role also strengthens security, resilience and maintenance of the company's legacy ecosystem.

Position Responsibilities

•Establish and lead the enterprise technology eco-system, data practices, AI and digital modernization strategy, ensuring alignment with organizational priorities, long-term objectives, and future-state business capabilities.
•Provide executive leadership and oversight of the organization's technology planning including enterprise applications, infrastructure, cybersecurity, data and analytics, cloud platforms, and the Program Management Office (PMO).
•Provide strategic oversight of the organization's legacy technology ecosystem while guiding the transition to modern enterprise cloud platforms, ensuring critical business operations remain uninterrupted and modernization objectives are achieved.
•Lead the implementation of digital modernization initiatives, including enterprise platforms, cloud solutions, data infrastructure, and AI-enabled solutions that improve service delivery and operational performance.
•Lead the development and advancement of enterprise data, analytics, and AI capabilities to enhance decision-making, generate insights, and support innovation across the organization.
•Establish and maintain enterprise technology governance, architecture, and standards to support informed decision-making, risk management, regulatory compliance, and system integration.
•Lead technology investment planning, budgeting, vendor partnerships, and contract management to maximize value and support organizational objectives.

Leadership Responsibilities

•Partner with the CEO to align, create, and communicate the organization's vision, mission, and long-term strategy, driving strategic clarity and execution across the organization.
•Collaborate with the CEO to co-create and drive strategic plans that advance organizational priorities and oversee execution of business initiatives.
•Lead the execution of strategic initiatives that fuel sustainable growth and strengthen financial outcomes across the organization.
•Develop senior leaders and shape the future leadership pipeline to ensure robust succession and long-term organizational success.
•Sponsor large scale transformations: digital, cultural, operational or structural to support strategic growth.
•Shape and drive a value-based culture within and across teams, promoting inclusion, accountability, and ethical behaviors.
•Navigate uncertainty with agility and sound judgment, leading the organization confidently through unknown and complex situations.

Competencies

•Continuous Improvement: Drives a culture of innovation and continuous improvement. Inspires and sets the direction for the modernization of systems and practices. Embraces outside-in thinking as a critical component to inform and inspire new ideas. Excels at creating and brainstorming in uncharted or unknown areas.
•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.
•Strategic Thinking & Vision: Defines and communicates a compelling vision that inspires direction and alignment. Looks forward to anticipate future trends and connects complex ideas to shape long-term strategy. Challenges assumptions, identifies bold opportunities, and influences decisions that position the organization for future long-term success.
•Critical Thinking & Judgement: Applies strategic insight and seasoned judgment in complex, critical, or uncharted situations. Navigates ambiguity with confidence and clarity, adapting to the unknown while maintaining focus on outcomes. Evaluates risk, considers diverse perspectives, and makes decisions that balance short and long-term implications and align with organizational priorities. Sees the big picture and connects the dots across systems, guiding others through complexity and change to drive meaningful outcomes.
•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.
•Customer Centric: Demonstrates a clear understanding of who our customers are – whether internal or external – and considers the customers 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.

Education & Experience

•Bachelor's or Master's degree in Information Technology, Computer Science, Engineering, Business Administration or business-related discipline, or an equivalent combination of education and senior level experience.
•10+ years' leadership experience at the executive or senior management level leading enterprise technology, data, and digital transformation functions.
•Proven success leading large-scale technology modernization and transformation initiatives.
•Experience overseeing enterprise applications, infrastructure, data, cybersecurity, and technology operations.
•Experience managing complex environments that balance operational stability with strategic change.
•Demonstrated experience leading cloud strategies and operating within multi-cloud environments, including Azure, AWS, and third-party vendor platforms.
•Proven ability to lead cross-functional teams, influence stakeholders, and communicate complex technology matters to executive and board audiences.
•Experience working in insurance, financial services, healthcare, or other highly regulated industry is considered an asset.

When you become a GMSer, you can expect:

•Competitive salary and bonus opportunities.
•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 Monday, August 3, 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.