Director, Technology Transformation & Data

Dream•Toronto, ON

1d•Onsite

About The Position

Dream is looking for a Director, Technology Transformation & Data to lead two interrelated mandates: driving the delivery of enterprise-wide transformation programs and building Dream’s emerging data and artificial intelligence capability. The ideal candidate is a technology leader who sits comfortably at the intersection of delivery and strategy, with a track record of running complex transformation programs and a genuine curiosity about data and AI. They thrive in environments where they have to build things, not just manage them, and are energized by the challenge of creating structure and capability where little currently exists. What matters most is that they have owned delivery, built capability, and brought business stakeholders along for the ride.

Requirements

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

Nice To Haves

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

Responsibilities

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