Senior Director, Business Systems & Enterprise Technology

WELL Health Technologies Corp is an omnichannel digital health company whose overarching objective is to empower doctors and healthcare practitioners to provide the best and most advanced care possible while leveraging the latest trends in digital health. 

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

• 48 accredited diagnostic health service locations across Ontario.
• 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.

At WELL, 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 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 Systems & Enterprise Technology to lead enterprise technology strategy and execution. As an innovative and results-driven leader, you will develop and optimize enterprise architecture, data services, service delivery, and business systems, including ERP, CRM, HRIS, and other enterprise applications. Your expertise will enable the organization to scale effectively, increasing automation, efficiency, and data-driven decision-making. You will drive the evolution of our enterprise technology 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. 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, 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, modernizing core systems such as ERP, CRM, HRIS, and data analytics platforms. Your leadership will ensure WELL Health’s technology infrastructure 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. WELL has grown significantly and continues 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:

• 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 data and 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 subsidiaries, developing a deep understanding of their operational challenges and technology requirements. As a trusted advisor, you will ensure that enterprise systems and digital strategies empower teams, enhance efficiency, and drive business performance.
• Define and execute the enterprise technology vision. You will architect a comprehensive enterprise systems strategy, integrating best-in-class ERP, CRM, HRIS, and automation technologies. Your leadership will ensure enterprise applications are optimized for scalability, agility, and data-driven decision-making.
• 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.
• 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.

• Note: See the full job description at the following link. https://tinyurl.com/4vbwta9e

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.

Apply now

Interested in applying but worried you don't have it all? At WELL, we know not everyone gains their experience following a traditional path. If you share our values, want to make a difference in healthcare technology solutions, and meet 70% of the qualifications, we encourage you to apply. Express your interest here.

What you can expect from our interview process:

• A virtual interview with a Talent Advisor to discuss your experience and interest in the role.
• An interview with the SVP Technology Services, where you will have the opportunity to showcase your thought leadership, strategic approach to enterprise systems architecture, and relationship-building expertise. This conversation will provide deeper insights into the organizational impact of the role, day-to-day responsibilities, and opportunities for career development and growth.
• A final interview with the COO, focusing on how this role aligns with the company’s broader strategic objectives. This will be an opportunity to discuss your vision for enterprise technology, your ability to drive business transformation, and how you can contribute to the company’s long-term success.

WELL is committed to supporting a diverse, inclusive, and accessible workplace. We welcome and celebrate the diversity of applicants and team members across ability, race, gender identity, sexual orientation, and perspective. We strive to create an inclusive workplace where differences are celebrated and fuel our success – this is the WELL Way! Accommodations are available on request for candidates taking part in all aspects of the selection process.

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