Title: Associate VP, Information Systems

Department: Information Systems

Reports To: COO/CFO & Executive Leadership Team

About Us The Madison Group is a family-owned, widely diversified real estate and land development company with a substantial portfolio of retail, commercial, and industrial projects.

The Madison

Group also has extensive experience in building master-planned communities, low-rise, and high-rise residential projects.

For over 55 years, The Madison Group has built its foundation on integrity and innovation and our commitment to our customers is our foremost priority.

The Madison

Group focuses on creating quality homes and residences in desirable areas firmly rooted in a sense of community. Our reputation is defined by the talent, dedication, and passion of our team.

For further information, please visit our website at madisongroup.ca

General Description The Associate VP, Information Systems will lead the overall technology strategy, operations, cybersecurity, infrastructure, business applications and digital transformation initiatives of The Madison Group.

This role ensures that technology supports business objectives, improves operational efficiency, protects company data and enables growth across all divisions. This position will work closely with third-party IT support service and technology providers, relevant business stakeholders, and project committees to ensure the consistent and successful delivery of each software application.

Primary Responsibilities

- Ensure the organization’s IT strategy aligns with corporate goals




- Identify opportunities to leverage technology to improve business performance
- Build and continuously update a road map that supports the company’s long-term growth
- Advise senior leadership of emerging technologies, risks and opportunities
- Oversee all IT infrastructure including networks, servers, cloud platforms, telecommunications, and end-user computing
- Lead all phases of the business systems implementation including planning, testing, execution, and implementation as well as assisting in implementation of upgrades and enhancements
- Develop and maintain the organization’s cybersecurity strategy, providing security awareness and training
- Oversee cybersecurity assessments and audits
- Manage disaster recovery, business continuity plans, incident response, vulnerability management and compliance requirements
- Ensure compliance with applicable privacy, security and regulatory requirements
- Establish and update policies for data management, retention, access controls and any other IT policies or procedures required company wide
- Research potential IT vendor alternatives, propose solutions, and manage contract negotiations
- Develop and manage the annual budget for Information Systems




- Ensure cost-effective procurement and utilization of technology assets
- Establish departmental objectives and performance expectations of the IT team
- Demonstrate valuable leadership skills with a positive attitude and ability to motivate others

Required Skills And Qualifications

- Bachelor’s degree or diploma in Computer Science or similar
- Preferably 10+ years experience in building and managing an IT team within a mid-size organization
- Experience in an IT role within construction/real estate development is a must
- Familiarity with New Star Constellation ERP, Hub Spot, SalesForce, Yardi, Power BI, Inform Excel is an asset
- Proven experience in project leadership.
- Experience in managing expectations and working in a multi-user/multi-division environment
- Exceptional leadership skills
- Ability to communicate and collaborate effectively with users, management, and project teams
- Excellent analytical, organizational, planning, and time management skills
- Ability to effectively manage multiple priorities simultaneously

Madison Group celebrates diversity and is proud to be an equal opportunity employer. We are committed to creating an inclusive environment for all employees and applicants and make all employment-related decisions without regard to race, color, religion, sex, national origin, sexual orientation, gender identity, age, disability. AI will not be used to screen resumes or during the interview process.

Compensation: $180K - $200K

📌 Associate VP, Information Systems (North York)
🏢 Madison Group of Companies
📍 North York