Director Software Engineering jobs in Montréal, QC

We are a well-established and rapidly growing real estate ownership, development, and property management organization with a diversified portfolio spanning industrial, commercial, office, retail, and residential assets. For decades, we have focused on long-term value creation through disciplined investment, operational excellence, and strategic expansion across multiple markets.

With approximately 500 employees and operations supported by both corporate and field-based teams, our organization relies heavily on technology to manage property operations, tenant services, financial systems, construction projects, and internal business functions. As we continue to modernize and scale, we are placing a strong emphasis on digital transformation, system integration, cybersecurity, and data-driven decision-making. To lead this evolution, we are seeking an experienced Chief Technology Officer (CTO) / Head of IT to join our executive leadership team.

This is a high-impact executive leadership role responsible for overseeing all aspects of technology strategy, infrastructure, and systems across the organization. The Chief Technology Officer will serve as both a strategic advisor and operational leader, ensuring that technology enables efficiency, scalability, and innovation across all business units.

This individual will be responsible for modernizing and managing the company's IT environment, including enterprise systems, property management platforms, financial systems, data infrastructure, cybersecurity, and internal support functions. A strong background in real estate technology or similarly complex, multi-site operational environments is highly valued.

The ideal candidate will be a hands-on technology leader who understands how to align IT strategy with business goals, improve operational workflows, and support a growing real estate organization through scalable, secure, and efficient systems.

Responsibilities

• Serve as the organization's senior technology leader and strategic partner to executive leadership, aligning technology initiatives with business objectives and growth strategy.
• Oversee all IT operations, infrastructure, systems, and support across a multi-site real estate organization with approximately 500 employees.
• Lead digital transformation initiatives, including modernization of legacy systems, process automation, and integration of property management, financial, and operational platforms.
• Develop and execute a long-term technology roadmap focused on scalability, efficiency, cybersecurity, and data-driven decision-making.
• Manage enterprise systems including ERP, property management software, CRM platforms, and internal business applications.
• Oversee cybersecurity strategy, risk management, data protection, and compliance with relevant regulations and industry standards.
• Lead vendor selection, contract negotiations, and management of external technology partners and service providers.
• Build and maintain a reliable, secure, and high-performing IT infrastructure supporting both corporate and field operations.
• Partner with business leaders to identify opportunities where technology can improve efficiency, reduce costs, and enhance tenant and employee experience.
• Lead, mentor, and develop the IT team while building a culture of accountability, responsiveness, and continuous improvement.
• Oversee IT budgeting, forecasting, and capital planning to ensure efficient allocation of resources.
• Evaluate emerging technologies and innovations relevant to real estate operations and long-term business growth.

Qualifications

• 10+ years of progressive technology leadership experience, including senior IT or CTO-level responsibility.
• Strong experience within real estate, property management, construction, facilities management, or similarly complex multi-site operational environments is required.
• Proven experience managing IT strategy for organizations with several hundred employees or more.
• Deep understanding of enterprise systems, infrastructure, cloud environments, cybersecurity, and data architecture.
• Experience leading digital transformation and system integration initiatives.
• Strong vendor management, procurement, and contract negotiation experience.
• Demonstrated ability to align technology strategy with business goals and operational needs.
• Experience managing IT budgets and driving cost-effective technology solutions.
• Strong leadership, communication, and stakeholder management skills.
• Ability to thrive in a fast-paced, growth-oriented, and operationally complex environment.
• Experience building and leading high-performing IT teams.

Compensation

• $200,000 – $275,000 base salary (depending on experience)
• Comprehensive benefits package
• Paid vacation and company holidays
• Professional development and leadership growth opportunities
• Opportunity to lead technology transformation within a large and established real estate organization
• Long-term strategic impact on enterprise systems, infrastructure, and digital innovation