Senior Director, Business Technology & AI Enablement

Our mission is to tech-enable healthcare providers. We do this by developing the best technologies, services, and support available, which ensures healthcare providers are empowered to positively impact patient outcomes. Our comprehensive healthcare and digital platform includes extensive front and back-office management software applications that help physicians run and secure their practices. Our solutions enable more than 37,000 healthcare providers between the US and Canada and power the largest owned and operated healthcare ecosystem in Canada with more than 200 clinics supporting primary care, specialized care, and diagnostic services. In the United States our solutions are focused on specialized markets such as the gastrointestinal market, women’s health, primary care, mental health, revenue cycle management, and practitioner recruiting.

As a recognized leader in specialty care, telehealth, and health services, our reach includes:

• >200 Primary and executive healthcare clinics in Canada and the U.S.
• A global Electronic Medical Records (EMR) network serving thousands of healthcare clinics and health systems.
• A multi-tiered portfolio of telehealth services, including one of Canada’s largest providers.
• Advanced digital health, billing, and cybersecurity solutions that optimize healthcare operations.
• Specialized support for thousands of U.S. Gastroenterology physicians through tailored products and services.

Our 4,500+ team members are at the center of everything we do, enabling healthcare providers to focus on what matters most—caring for their patients. From developing innovative technology and services that optimize care delivery to empowering patients to take control of their health, our people are making a measurable impact in the markets we serve.

This is a rare opportunity to shape the future of enterprise technology at a high-growth, mission-driven organization. If you are a visionary eager to drive transformation through technology, we invite you to join us.

The opportunity

Reporting to the SVP Technology Services, we are hiring a Senior Director, Business Technology & AI Enablement to lead enterprise systems strategy and execution. As an innovative and results-driven leader, you will develop and optimize enterprise architecture, with a key focus on strategy, design, implementation, and roll-out of centralized CRM, ERP and HRIS systems for the corporation. In addition, developing the Enterprise Application Roadmap to underpin business growth and AI-driven business process automation will be a significant part of the role. Your expertise will enable our rapidly growing organization to scale effectively, increasing automation, efficiency, and data-driven decision-making. As a member of the Technology Shared Services Leadership team, you will drive the evolution of our enterprise systems landscape, ensuring alignment with business objectives and industry best practices.

This is a remote role with the opportunity to work as needed from our Toronto or Vancouver offices, depending on your location.

Who you are

You are a leader who seamlessly blends technical expertise with business acumen. You excel at solving complex business challenges, working cross-functionally with senior management, and fostering collaboration between functional and technical teams as a leader in the corporate shared service function. You are looking for the next opportunity in your career where you can apply your strategic leadership capabilities and business insights to lead digital transformation at scale, drive efficiency through technology, and contribute to a company that is redefining healthcare.

What’s in it for you

Purpose. This is a rare opportunity to shape the future of enterprise technology at a mission-driven organization. Your leadership will drive internal digital transformation, optimizing corporate systems, enterprise applications, and business processes to enhance efficiency, improve decision-making, and enable teams to focus on what matters most—supporting healthcare providers and improving patient outcomes.

Influence. You want to have strategic influence across a growing enterprise. You will collaborate with executive leadership and key decision-makers across multiple business units and corporate functions, shaping the technology vision and enterprise architecture for a rapidly expanding healthcare technology ecosystem. Your ability to align systems, data, and automation strategies will drive enterprise-wide efficiencies.

Ownership. This is an opportunity to define, build, and execute a comprehensive roadmap for enterprise applications, rapidly modernizing core systems such as ERP, CRM, HRIS, and associated business processes. You have a strong ability to understand existing business processes, define optimized and AI-enabled enhancements, lead the implementation, and support the business through significant change. Your leadership will ensure WELL Health’s enterprise application roadmap is scalable, agile, and future-ready.

Autonomy. You want to drive innovation and transformation. You will have the freedom to introduce cutting-edge AI, automation, and analytics solutions, optimize workflows, and enhance business intelligence capabilities. Your vision will shape how WELL leverages technology to accelerate growth and increase efficiency across all subsidiaries.

Career development. We have grown significantly and continue to scale through demand for our solutions, resulting in financial success and a proven acquisition strategy. You will gain exposure to complex M&A integrations, enterprise-wide system transformations, and large-scale digital strategy execution. As we continue to transform, you will have the chance to expand your leadership scope and take on new challenges across the organization.

You will:

• Define and execute the enterprise technology vision. You will architect a comprehensive enterprise systems strategy, integrating best-in-class ERP, CRM, HRIS, and AI-enabled automation technologies. Your leadership will ensure enterprise applications are optimized for scalability, agility, and data-driven decision-making.
• Lead enterprise roadmap development and execution. You will be responsible for the selection, deployment, and governance of core enterprise systems, ensuring they are seamlessly integrated and continuously evolved to meet business demands. Your vision will set the foundation for long-term technological advancement and operational excellence.
• Harness the power of data and AI. You will oversee enterprise-wide AI-enablement strategy, underpinned by a solid data foundation and a desire to drive business process automation at scale. You will leverage AI solutions to enable Enterprise Search, Agentic Workflow Automation, Customer Service, Knowledge and Documentation. You will also be proficient in the use of Microsoft Fabric, Snowflake, and AI-driven analytics to provide actionable insights and unlock new efficiencies.
• Champion innovation and enterprise-wide digital transformation. You will drive the modernization of CRM, ERP, and HRIS systems to maximize productivity, elevate user experience, and future-proof operations.
• Lead M&A technology integration. As the company expands through acquisitions, you will conduct technology due diligence, assess enterprise system compatibility, and lead the seamless integration of acquired businesses. Your expertise will ensure rapid alignment with corporate standards, enabling operational continuity and synergy realization.
• Build and lead a high-impact technology team. You will mentor, develop, and inspire a team of data analysts, enterprise architects, and service delivery managers, fostering a culture of innovation, collaboration, and continuous improvement.
• Define and execute key strategies and roadmaps. You will own and drive the enterprise applications and data analytics strategy, ensuring alignment with business objectives and growth trajectories. You will define and develop a roadmap for business systems and enterprise applications, leveraging automation and AI to maximize efficiency and scalability.
• Cultivate strategic partnerships and align business needs. You will engage with senior leaders across corporate functions and subsidiaries, developing a deep understanding of their operational challenges and technology requirements. As a trusted advisor, you will ensure that enterprise systems, processes, and digital strategies empower teams, enhance efficiency, and drive business performance.
• Drive prioritization and resource optimization. You will establish a structured approach to evaluating, prioritizing, and executing technology initiatives, balancing strategic business needs, ROI, and cross-functional impact. You will navigate complex stakeholder landscapes, resolving competing demands to advance the organization’s digital capabilities.

You bring:

• Strategic and transformational leadership. You are an accomplished technology leader with a track record of architecting and driving enterprise-wide system modernization, implementing automation, and optimizing business operations. You are adept at navigating complex challenges, gaining insights into business needs and translating them into technical requirements. You have an exceptional ability to build stakeholder trust and can prioritize conflicting demands to deliver high-impact solutions.
• Deep enterprise systems expertise. You have extensive experience managing ERP, CRM, HRIS, and other core business applications. You have successfully led enterprise platform selection, implementation, and integration, ensuring they drive measurable business value. Experience with M&A integrations is an asset.
• Experience driving innovation through AI, Automation and Data. You are highly proficient in data analytics, business process automation, and AI-driven solutions. You use AI tools in many areas of your work to drive efficiency and innovation. You inspire others to adopt new ways of working through demonstrating AI use cases and opportunities. You have hands-on experience with platforms such as Dynamics 365 F&O, Dynamics 365 CRM, Salesforce, Freshworks, Power BI, Power Automate, FiveTran, or Snowflake.
• Operational and financial acumen. You have experience overseeing budgeting, vendor negotiations, and ROI-driven technology investments. You bring a results-oriented mindset and a keen ability to balance strategic vision with operational execution.
• Resilience. You thrive in fast-paced environments, embrace change, and continuously seek opportunities to innovate and improve. You lead with integrity, transparency, and a commitment to excellence.

Why join us?

Healthcare is our sector, and we know that for WELL to be a winning team, we must provide an open environment to prioritize health and wellbeing and multiple resources to discuss mental, physical, and psychological needs openly. From the CEO to the newest hire, everyone comes together as part of our culture of respect, openness, support, and communication. We unite to empower each other to be the best we can be.

We recognize that the best way to serve our diverse patient communities is by reflecting that diversity. With almost 65% of our team members identifying as female and 70% of our leadership identifying as a visible minority, we are proud of our diverse, equitable and inclusive organization.