Director,Technology Transformation & Data Job Toronto area,Ontario Canada,IT/Tech

What will you do?

Technology Transformation Programs

Lead the PMO function: govern Dream’s technology project portfolio using a defined methodology, best practices, and structured delivery frameworks;

Drive the selection and implementation of new enterprise solutions — working with business stakeholders to define requirements, evaluate vendors, and oversee delivery end to end;

Ensure transformation initiatives are delivered on time, on scope, and with measurable business outcomes; capture and apply lessons learned across the portfolio;

Build a culture of structured change delivery across the Technology team and business stakeholders;

Data & AI Strategy and Delivery

Define and execute Dream’s data and AI roadmap — identifying high-value use cases across the business and building the foundation (governance, infrastructure, tooling) to deliver them;

Hire, onboard, and develop a data and AI capability into a high-performing function over time;

Evaluate and pilot AI tools and automation opportunities that improve efficiency and decision-making across Dream’s business units;

Partner with Enterprise Systems and Technology Operations to ensure data quality, accessibility, and governance are embedded in day-to-day operations;

Work closely with the Cyber Security team to ensure data and AI initiatives are designed and delivered with security and privacy considerations embedded from the outset;

Leadership & Stakeholder Management

Act as a senior technology partner to business leaders across the Dream group, translating strategic priorities into executable technology initiatives;

Manage a lean, high-trust team — setting clear expectations, developing talent, and modelling the collaborative culture Dream’s Technology team is known for; and

Report on transformation and data program progress to the VP & CIO and, where relevant, to senior business leadership.

What skills and qualifications should you have?

The right candidate has a proven track record and the right combination of skills and mindset to lead both mandates from day one.

Must Haves:

Demonstrated experience leading technology transformation or digital change programs — you have owned delivery end-to-end, not just supported it;

A genuine curiosity about data and AI — you do not need to be a data scientist, but you need to have built or been close to building a data-oriented function;

Strong program governance skills: you know how to run a portfolio, manage risk, and keep stakeholders aligned across complex, multi-workstream initiatives;

Exceptional communication skills — you know how to bring business and technology stakeholders along, translating complex ideas into clear, compelling narratives at every level of the organization;

Familiarity with the Microsoft data and analytics stack, including Azure, Microsoft Fabric, Databricks, and Power BI; and

A builder’s mindset: comfortable with ambiguity, energized by creating structure and capability where little currently exists.

Strong Assets:

Experience in real estate, asset management, financial services, or similarly complex, multi-entity organizations;

A background that spans both project/program delivery and technology strategy — not one or the other; and

Experience hiring and developing data, analytics, and project management talent.

Who Are We?

Dream Unlimited is an award-winning Canadian real estate investment, development and management company with approximately $28 billion of assets under management in North America and Europe. Our scope of business includes asset management and management services for both publicly listed real estate as well as private capital.

Dream has grown substantially since its formation in 1996, becoming one of Canada’s leading real estate companies with a diverse workforce in North America and Europe. We are one of Canada’s largest developers, building communities for people to live in; developing land, homes, condominiums, retail centers and renewable power projects. We also build communities to work in, bringing office, industrial and retail spaces to life.

We invest in and manage properties, enriching them for the people who work here and the greater community.

Our entrepreneurial spirit…

Director, Technology Transformation & Data