Director, Enterprise Systems, Data & AI

Are you passionate about using technology to improve organizational effectiveness and build stronger communities?

We're looking for a strategic, curious and collaborative leader who can bridge business and technology, helping turn ideas into practical solutions that enable our people and organization to thrive so that we can better strengthen our community.

ABOUT TORONTO FOUNDATION

Toronto Foundation is the home of collective investing and impact. We’re a registered charity and one of 208 community foundations in Canada. Our research tells us that social cohesion is Toronto’s most important vital sign, so we’re using our tools and resources to build community wellbeing.

We are home to over 1,000 community-minded philanthropists and charitable organizations and collectively administer over $550 million in charitable assets. Together with our fundholders, we granted over $37.7 million in 2025 to organizations working to improve the quality of life in Toronto.

We are committed to listening, learning and working in partnership with communities and invite you to join us in tackling the inequities we face in our city.

WHO WE ARE LOOKING FOR

You're a curious, strategic thinker who enjoys solving complex organizational challenges through technology, data and innovation. You see systems not as ends in themselves, but as tools that enable people to make better decisions, work more effectively and create greater impact.

Equally comfortable discussing enterprise architecture with technical partners or facilitating conversations with senior leaders, you naturally bridge business needs with practical technology solutions.

Reporting to the Chief Operating Officer (COO), the Director, Enterprise Systems, Data & AI serves as a trusted business partner across the organization.

The role provides strategic leadership for enterprise systems, data governance, reporting and analytics, Artificial Intelligence (AI) enablement and digital transformation, ensuring Toronto Foundation's technology investments support informed decision-making, operational excellence and long-term organizational success.

Working collaboratively across all departments, you build strong relationships, challenge existing ways of working and help others embrace new technologies and processes with confidence. You are equally comfortable thinking strategically, leading change and rolling up your sleeves to solve problems, guide implementation and deliver practical results.

You stay connected to emerging technologies and industry best practices, continuously identifying opportunities to strengthen organizational effectiveness, improve decision-making and enable Toronto Foundation to deliver greater impact.

CORE AREAS OF RESPONSIBILITY

Enterprise Systems & Digital Enablement

Lead the strategy, governance, integration, optimization and ongoing evolution of enterprise systems and digital capabilities that support organizational effectiveness, scalability and informed decision-making.

Key Responsibilities

• Establish and maintain effective relationships with managed service providers and technology vendors, including performance monitoring, contract oversight, service delivery expectations and alignment with organizational priorities.
• Build and leverage relationships with technology partners, sector peers and professional networks to ensure Toronto Foundation capitalizes on emerging practices, innovations and insights that enhance organizational effectiveness and digital maturity.
• Lead the ongoing optimization, governance and evolution of Toronto Foundation's technology ecosystem, including Salesforce, Microsoft 365, SharePoint, Teamflect, Sage Intacct integrations and other business platforms.
• Establish and oversee a governance framework for the responsible, secure and effective use of artificial intelligence across Toronto Foundation.
• Oversee enterprise systems, technology, data architecture and platform integrations to ensure organizational systems remain aligned, scalable and capable of supporting reliable reporting, analytics and decision-making.
• Work closely with the COO to establish and maintain governance, policies, standards and oversight processes for enterprise systems, data, artificial intelligence and emerging technologies, ensuring responsible use and appropriate management of organizational risk.
• Partner with departments to understand business requirements and translate them into effective technology solutions.
• Partner with departments to assist in the development and refinement of processes to ensure that teams are fully utilizing Toronto foundation’s systems and technology.

Success Measures

• Strong adoption and satisfaction across enterprise systems and digital platforms.
• Successful delivery of priority technology and systems initiatives.
• Improved integration, reliability and scalability of enterprise systems.
• Reduced operational inefficiencies through automation and process improvement.
• Effective governance and risk management practices for systems, data and emerging technologies.

Data, Reporting & Decision Support

Provide enterprise-wide leadership for data governance, reporting, analytics and decision-support that enables informed organizational decision-making.

Key Responsibilities

• Act as a strategic business partner to departments across Toronto Foundation, translating business needs into data, reporting, systems, automation and technology solutions that support operational effectiveness and strategic decision-making.
• Ensure and drive the quality, integrity, consistency and accessibility of organizational data.
• Work closely with the COO in the design and delivery of enterprise reporting, dashboards and performance metrics aligned with organizational priorities and Objectives and Key Results (OKRs) for both internal and external stakeholders.

Success Measures

• Improved data quality, integrity and governance maturity across Toronto Foundation’s teams and enterprise systems.
• Increased use of reporting and analytics in organizational decision-making.
• Timely, accurate and meaningful reporting to management and governance bodies.
• Increased visibility into organizational performance, outcomes and strategic priorities.

Organizational Learning & Enablement

Leads organizational enablement, adoption and capability-building initiatives that help staff effectively leverage enterprise systems, data, digital tools and new technologies to improve performance, collaboration and decision-making.

Key Responsibilities

• Lead change management, adoption, training and capability-building initiatives that enable staff to effectively leverage enterprise systems, AI tools, digital platforms and new ways of working.
• Coordinate annual cybersecurity awareness training, cyber preparedness, response & remediation initiatives and technology-related business continuity planning in partnership with managed service providers and external specialists.
• Support a culture of continuous improvement, collaboration, learning and adaptability across the organization.
• Lead organizational change management and user adoption initiatives associated with new systems, technology and digital capabilities.

Success Measures

• Increased adoption and value realization from enterprise systems and digital investments.
• Enhanced staff capability and confidence in leveraging technology, data and AI tools.
• Effective implementation of organizational change initiatives.
• Strengthened cybersecurity awareness and technology risk preparedness.
• Continuous improvement and innovation embedded in organizational practices.

WHAT WE OFFER

Full-time employment with an excellent benefits package that includes

• 35-hour work week
• Hybrid workplace
• 4 weeks of vacation per year
• Summer Fridays off between Canada Day and Labour Day
• RRSP matching
• Family health plan
• Salary range between $100,000 p.a. - $120,000 p.a.

We believe the greatest ideas come from a diverse mix of minds, backgrounds and experiences and are committed to cultivating an inclusive work environment. Toronto Foundation actively seeks a diverse applicant pool and encourages candidates of all backgrounds to apply, especially those from marginalized communities.

Toronto Foundation is committed to the principles of the Accessibility for Ontarians with Disabilities Act (AODA). As such, we strive to make our recruitment, assessment and selection processes as accessible as possible and provide accommodations as required for applicants with disabilities.

Find the full list of knowledge, skills, attributes, required qualifications and what we offer at: torontofoundation.ca/were-hiring-director-enterprise-systems-data-ai

SUBMISSION DETAILS

In lieu of a standard cover letter, please respond to the following statements in less than 750 words describing:

• What attracted you to this opportunity and Toronto Foundation.
• Which aspects of your experience best prepare you to succeed in this role.
• What you see as the greatest opportunity for organizations to improve through systems, data, AI, or digital enablement.

You may submit your response to the above question along with your resume in confidence to resumes@torontofoundation.ca and include the position title and your name in the subject line of the email (e.g. Director, Enterprise Systems, Data & AI, First Name and Last Name).

Please ensure both documents are attached in a single PDF file.

Applications will be assessed on a rolling basis and the posting will close on August 24, 2026, at 5pm EDT.

Applicants must be eligible to work in Canada at the time of application. We thank all applicants for their interest in Toronto Foundation. However, due to the high volume of applications we receive, only those considered for an interview or those invited to participate in an assessment will be contacted.