Digital Transformation & AI Director

About Scott Mission

Scott Mission began in 1941 through the efforts of Rev. Morris and Mrs. Annie Zeidman as a Christian, non-denominational organization. Every year, it provides practical, emotional, and spiritual assistance to thousands of people in Toronto who are facing poverty and homelessness.

The Mission is guided by a community culture that aims to be centered on Jesus Christ, generous and collaborative in relationships, servant-hearted and professional in its work, and grounded in God’s rescuing work throughout history. Its vision is captured in the prayerful goal of seeing poverty fully retreat and flourishing grow for all people in Toronto and beyond.

The organization is carrying out a five-year strategic plan focused on expanding capacity and basic-needs services, strengthening transformational impact for clients, growing partnerships, and providing spiritual leadership in Canada.

Position Overview

The Digital Transformation & AI Director is a senior enterprise leadership role responsible for turning the Mission’s transformation agenda into a practical, sequenced plan of action. This person will identify where work can be simplified, automated, or redesigned across the organization, while also safeguarding the quality and integrity of data across donor, constituent, and operational systems.

The role will partner with internal teams to evaluate and deploy the most effective AI tools for each function, while also owning the implementation roadmap for projects and processes. It will lead AI adoption across the organization by prioritizing programs and pilot initiatives, and success will be measured by improved efficiency, effective use, strong adoption, and meaningful outcomes across operations.

This position must ensure that AI and digital strategy are applied in ways that uphold donor trust, client dignity, staff wellbeing, privacy, and security. It is intended for a leader who can connect technical complexity with organizational goals and drive visible change in structure, process, and performance.

The role is also suited to someone who has launched AI agents in production, pays close attention to evaluation and observability, and wants the freedom to build systems that become more valuable over time.

Reporting Structure

This position reports to the Chief Operations Officer (COO) and is part of the Leadership Team.

Key Responsibilities

• Design and build AI agents capable of running workflows independently from the ground up.
• Develop and steward a multi-year AI strategy that supports organizational growth and mission impact.
• Own the digital transformation roadmap and guide end-to-end implementation.
• Review data quality across core systems, including de-duplication and basic governance practices.
• Convert the Mission’s transformation vision into a clear execution plan with defined priorities and sequencing.
• Work with Ministry programs, Finance, Operations, and Marketing & Philanthropy to build understanding, support adoption, and embed training into each area.
• Lead pilot initiatives and determine which solutions should scale and which should be discontinued.
• Track success using adoption, impact, and efficiency indicators.
• Develop agents that reliably take on work and perform with transparency and effectiveness.
• Design workflows, learning plans, monitoring methods, and trust-building processes that support adoption of technology across teams.
• Set the enterprise AI roadmap, including priority areas, implementation plans, training, and outcome targets.
• Contribute to future-state thinking on how technology should be used within the Mission.
• Partner with leaders across the organization to help them understand and embrace transformation.
• Create plans that show how technology can modernize operations, reduce inefficiencies, and improve strategic decision-making through data.
• Define KPIs, dashboards, and analytics approaches to measure effectiveness and support continuous improvement.
• Model inclusive leadership in cross-functional collaboration.

Qualifications

Education: A bachelor’s degree in a computer or information science discipline such as computer programming, software development, management information systems, or applied mathematics is required. A master’s degree is preferred.

Experience: Candidates should bring 8–12+ years of progressive experience in organization-wide IT and technology strategy, including at least 5 years in a leadership capacity. Experience leading major technology change initiatives that advance organizational goals and growth is required. Strong exposure to digital marketing platforms, CRM systems, and client-focused technologies is also expected. The ideal candidate must have a track record of helping teams understand, adopt, and effectively use technology to achieve measurable results.

Application Requirements

Applicants are asked to send a resume and cover letter to the hiring team. Employment depends on the results of a police reference check and satisfactory references.

Accessibility Statement

The organization welcomes applications from people with disabilities. Accommodations are available on request for candidates participating in every stage of the selection process.

Compensation

The salary range for this position is $110,000 to $125,000.

Notes

This role is based in Toronto, Ontario, Canada and is an on-site full-time position.