Digital Transformation & AI Director

Digital Transformation & AI Director

Scott Mission was founded in 1941 by Rev. Morris and Mrs. Annie Zeidman as a non-denominational Christian organization. Each year, it offers practical, emotional, and spiritual support to thousands of people who are experiencing poverty and homelessness in the City of Toronto. The Mission is a community that continually seeks to be:

• Centered in and dependent on Jesus Christ
• Gracious, generous, and collaborative in our relationships
• Servant hearted, innovative, and professional in our work
• Rooted in God’s rescuing work in history

Scott Mission’s vision prayer captures the heart of its goal: Poverty in full retreat, flourishing for all, in Toronto and beyond.

The Mission is currently implementing a transformational, five-year strategic plan with the following objectives: Increasing capacity and enhancing basic needs services, deepening clients’ transformational impact, multiplying partnerships, and offering spiritual leadership to Canadians.

Reports to: Chief Operations Officer (COO)

Member of: Leadership Team

Salary: $110,000 to $125,000

Position Summary

The Digital Transformation & AI Director is a broad leadership role with enterprise-wide responsibilities. This leader will turn the Mission’s transformation vision into clear, sequenced execution. They will define what should be simplified, automated and redesigned across all functional areas. This role will be outcome based and hold responsibility for the integrity of data across our core systems (donor, constituent and operational). The role will work with internal teams to assess and deploy the best AI efficiency tools for each area and will own the process and project implementation roadmap. The Digital Transformation and AI Director will lead AI adoption across the organization, owning the roadmap and the prioritization of programs and pilot projects. Success will be measured through effective use, impact, efficiency across all operational areas, while ensuring that our AI strategy and programs is used in ways that respect Donor Trust, Client Dignity, Staff Wellbeing and Privacy and Security. This role bridges the gap between complex technical needs and broad organizational objectives. This leadership role requires an innovative leader who encompasses the Mission strategy and can use technology to enact real measured change in process and structure.

This isn't a role where you use AI as a productivity tool. It's a role where you architect AI systems that do the work, run 24/7, and get better over time. You're part product thinker, part engineer — someone who can look at a workflow and break it into the agent primitives needed to automate it reliably at scale.

If you've shipped agents in production, obsess over evals and observability, and want real autonomy to build systems that compound — this is the role for you.

Primary Responsibilities

1. Enterprise Digital Transformation & AI Implementation

• Build AI agents from scratch to autonomously run workflows.
• Architect and lead a multi-year, enterprise-wide AI strategy aligned with organizational growth and impact goals.
• Provide the roadmap and manage the execution of our Digital Transformation Plan.
• Assess the integrity of our data across core systems. Oversee data quality, de-duplication and basic governance.
• Turn the Mission’s existing transformational vision into clear, sequenced execution. Define what should be simplified, automated and redesigned.
• Drive adoption and change. Partner with Ministry programs, Finance, Operations and Marketing & Philanthropy to ensure leadership wholly understands and embraces Digital Transformation and supports the training and integration into their areas.

2. Technology Leadership

• Lead pilot projects and decide what should scale and what should stop.
• Measure success through the integrated use, impact, high level of adoption and efficiency outcomes.
• Build the agents that take on the work and ensure they are honest and effective.
• Use your vertical technology expertise to design the flow, build the training programs, monitor the outcomes, catch failures and build trust so technology is effectively adopted and the use and trust are high.
• Own the enterprise wide roadmap for the use of AI technology, define the prioritized areas, the training and implementation plans and the outcomes.
• Envision how technology is used within the Mission and contribute to future strategy.

3. Vertical Performance & Team Leadership

• This leadership may or may not have direct reports but requires true partnership with all leadership levels across the organization. This leader can engage functional leaders to adopt the Transformation Strategy, can articulate the benefits of adoption and change and ensure that leaders embrace the change and can speak to the benefits. 
• Build a plan and engage all functional leaders in understanding how technology can modernize their operations, reduce inefficiencies, provide data to inform their strategies and provide executional excellence.
• Establish key performance indicators (KPIs), dashboards, and data analytics to monitor effectiveness and drive continuous improvement.
• Model an inclusive leadership approach.

Qualifications

Education

• Bachelor’s degree in a computer or information science field such as computer programming, software development, management information systems or applied mathematics. Master’s degree preferred.

Experience

• 8–12+ years of progressive experience in strategic, organization wide IT and Technology, with a minimum of 5 years in leadership role.
• Demonstrated success leading complex technological change strategies that support the organizations objectives and drive growth.
• Expertise in digital marketing platforms, CRM systems and client centric technologies.
• Proven ability to drive the understanding, adoption and utilization of technological tools to drive real, measured outcomes.

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· Interested applicants are invited to send a resume with cover letter to: View email address on ca.talent.com

· The Scott Mission welcomes and encourages applications from people with disabilities.

· Accommodations are available on request for candidates taking part in all aspects of the selection process.

· Employment is conditional to results of Police Reference Check and satisfactory reference