Director of Information Technology

About Cressey

Located in Vancouver, Cressey Development Group is a leading real estate firm established over 55 years ago. We create exceptional homes, communities, and commercial spaces that redefine how people live, work, and connect. With a commitment to superior design and quality construction, Cressey continues to build on a legacy of excellence. This is Where Great Places Begin. This is Cressey.

Role Overview

The IT Director reports directly to the Chief Financial Officer and own Cressey's technology stack end to end, from the ERP platform and other business applications to infrastructure, security, and day-to-day support. You will set the department's direction while staying hands-on: configuring and improving systems, resolving integration challenges, and working closely with leaders across development, construction, property management, and other business operations to deliver practical, scalable solutions. You will lead a lean team of five IT professionals, and manage additional support from external partners.

You will thrive in this role if you enjoy running an IT function while staying close to the technology, bring deep application expertise, and are energized by improving systems and troubleshooting problems.

Key Responsibilities

• Application Strategy and Delivery – own the strategy, roadmap, configuration, and ongoing improvement of Cressey’s ERP system (Yardi) and the broader application portfolio, including operational, financial, and reporting systems.
• IT Operations and Security – oversee IT infrastructure, end-user support, cybersecurity, and business continuity, delivered through the internal team and a managed-service partner; own security and risk mitigation, including controls, access, backups, and recovery.
• Business Partnership – partner directly with development, construction, property management, sales and marketing, and finance to understand operational challenges, deliver practical solutions, and support adoption of tools and technology through training and change management.
• End-to-End Project Leadership – lead application initiatives from requirements gathering through solution selection, configuration, integration, data migration, testing, deployment, and optimization, while remaining close to the work.
• Integration Ownership – take ownership of the integration layer between systems, ensuring data flows are reliable, documented, and secure, and removing reliance on any single individual or vendor.
• Portfolio and Budget Management – manage the technology portfolio, including project prioritization, operating and capital budgets, licensing, and contracts, with a focus on cost effectiveness and risk management as Cressey's Yardi footprint grows.
• Team Leadership – coach and develop a lean, service-oriented IT team by setting clear priorities, providing hands-on guidance, and building capability across applications and infrastructure.
• Vendor and Partner Management – actively manage relationships with Cressey's infrastructure and application service partners, ensuring accountability for performance, value, and long-term effectiveness.
• Standards and Governance – establish and refine practical standards for application configuration, data quality, access management, and documentation; this includes appropriate privacy and records management.

Experience Required

Cressey is looking beyond titles and tenure. What matters most is experience successfully running, improving, and supporting an ERP in an environment similar in size, stage, and scale, so you can immediately add value and strategic impact to the IT function.

• Applications - you are proficient in implementing, configuring, troubleshooting, and maintaining various software applications (e.g. Yardi, Sage, MRI, RealPage or similar).
• Right-Sized Environment -you have recently worked in and prefer a lean IT function - a small team supported by external partners.
• Vendor Management - you have managed service providers and implementation partners from both an operational and commercial perspective, including scope, performance, cost, renewals, and overall value.
• Communication - you have built trust with non-technical leaders, translated business needs into practical solutions, and led change management that made new processes stick.
• Infrastructure and Security Oversight - you bring sound judgment and technical knowledge to assess risk and set direction.
• Leadership - you have a demonstrated ability to guide, mentor, and develop team members, while fostering a collaborative and high-performance work environment.
• Education - Bachelor’s degree in Computer Science, Information Technology (IT), or related field appreciated, but experience is the primary consideration.

Compensation and Search Process

This role is based in Vancouver and performed primarily in the office with some flexibility for remote work on occasion. Hours can be flexibly scheduled to meet personal and professional needs, while supporting core business hours of 9:30 am - 4:00 pm. Availability for some travel to sites and technical support outside regular business hours, but this is not expected to be significant. Applicants must be willing to undergo a criminal record check.

Interested?

Visit Jane Hill Consulting to apply.

Applicants will be considered through November 6th, 2026 and may be contacted before the deadline. All qualified candidates legally eligible to work in Canada are encouraged to apply; however, Canadians and permanent residents will be given priority. We thank you for your interest. Qualified candidates will be contacted.