Mathew Chacko

Senior digital and enterprise transformation executive with more than 30 years of leadership experience across information technology, digital strategy, operations, and organizational modernization. Recognized for leading complex transformation mandates at scale and for combining strategic vision with disciplined execution to strengthen governance, improve performance, and deliver measurable enterprise and health system value. Brings a business-led approach to technology leadership, with deep experience advancing secure, interoperable, patient-centred digital services across complex healthcare and government environments.

Known for influencing executive stakeholders, leading large digital ecosystems, and enabling modernization, resilience, and system-wide impact through disciplined delivery and strong organizational leadership.

Vice President, Strategy & Portfolio Management - Ontario Health - Toronto

(2025-01)

Provide executive leadership for a multidisciplinary team spanning strategy, enterprise architecture, digital standards, risk, and change management, with a mandate to advance business and technology transformation across a complex digital health portfolio. Lead strategic planning, governance, and organizational change initiatives that strengthen alignment between enterprise priorities, digital investment decisions, and operational execution.

• Lead a multidisciplinary team of up to 500 professionals across strategy, architecture, standards, risk, product and change management. Oversee strategic planning and governance across a portfolio of 800 initiatives / $500M budget / enterprise-wide priorities
• Maintained and enhanced a close working relationships with various Ministry groups to advance objectives and secure support for key healthcare deliverables.
• Cultivated and sustained strategic partnerships with leading technology vendors and health system delivery partners—including Ocean, Orion, SmileCDR, Microsoft, AWS, Oracle, Epic, and MEDITECH—to advance organizational objectives and enable successful delivery across the digital health ecosystem.
• Lead strategic transformation initiatives across the portfolio, aligning business and technology priorities to support use of AI & automation for increased efficiency, faster delivery, modernization, stronger governance, and improved execution discipline.
• Led the development of the LDG expansion program in collaboration with stakeholders across the Ministry, hospitals, and other care sectors, mobilizing a high-performing cross-functional team of subject matter experts to advance a strategically significant initiative aimed at building a more coordinated and integrated health system.
• Led development of the portfolio operating plan and integrated book of work, establishing stronger traceability to a modernized gating and governance model aligned with enterprise operational practices.
• Provided cybersecurity, product and operational leadership on modernizing EHR assets, Primary Care, eReferral, Central Intake and other Pb4P initiatives, ensuring alignment to organizational priorities, service expectations, and transformation objectives.
• Provided architectural expertise to the Primary Care Digital Transformation project which is a highly interoperable and connected electronic medical record for primary care across the province.

Senior Director, Planning & Portfolio Management - Ontario Health - Toronto

(2023-01 - 2025-01)

Provide executive leadership for a multidisciplinary team spanning strategy, enterprise architecture, digital standards, risk, and change management, with a mandate to advance business and technology transformation across a complex digital health portfolio. Lead strategic planning, governance, and organizational change initiatives that strengthen alignment between enterprise priorities, digital investment decisions, and operational execution.

• Directed an integrated portfolio of complex, cross-functional programs, driving prioritization, execution discipline, and measurable value realization
• Optimized operational performance through enterprise business architecture, governance, and financial stewardship, improving efficiency, cost-effectiveness, and delivery consistency
• Established and enforced governance, risk, and performance frameworks, enhancing KPI attainment, compliance, and transparency across digital initiatives
• Partnered with senior executives, ministries, and external stakeholders to drive integrated planning, strengthen alignment, and deliver shared strategic outcomes
• Built and led high-performing, multidisciplinary teams, advancing talent strategy, leadership capability, and organizational performance at scale
• Led cloud transformation initiatives at scale, advancing enterprise modernization through stronger governance, security, architecture, and adoption of scalable digital capabilities.

Director, Cloud & Transformation Centers of Excellence - Ontario Health - Toronto

(2020-01 - 2023-01)

Director, Digital Strategy, Architecture & Security - Ontario Health - Toronto

(2018-01 - 2020-01)

Director, Service Management & Operations - Ontario Health - Toronto

(2016-01 - 2018-01)

IT Operations Manager - Ontario Health - Toronto

(2014-01 - 2016-01)

Infrastructure Architect - Ontario Health - Toronto

(2008-01 - 2014-01)

B. Eng. - Computer Science - BIET, Bangalore, India (1989-01 - 1996-01)

MBA Essentials for Managers - University of Toronto (2016-01 - 2017-01)