Vice-President, Information Technology

A NEW BREED OF ENTERTAINMENT

With almost 150 years of proud horseracing history, Woodbine Entertainment Group is the founding pioneer and largest operator of professional horseracing in Canada.

Building on our rich past, we are surging ahead to the future with an energized, new vision. Today we deliver the most thrilling and highest quality racing, dining and entertainment experiences to our visitors. In doing so, we remain a world-leader in horse-racing — and also among the most exciting and diverse entertainment facilities on the globe.

Position Overview

Reporting to the EVP, Finance, Operations & Technology, the Vice President, Information Technology (VP, IT) is a key executive responsible for shaping, leading, and executing Woodbine’s technology vision. This role oversees all aspects of IT Operations (infrastructure, network, cloud), Support, Cyber Security, Product Management, Data & Integration, and Broadcast Technology.

The VP, IT provides strategic direction while ensuring day‑to‑day operational excellence across all technology functions. This leader will partner closely with business stakeholders across the organization to align technology solutions with Woodbine’s enterprise strategy, drive innovation, and enable exceptional customer and employee experiences.

Key Accountabilities

Strategic Leadership & Vision

· Build multi‑year technology strategies for IT Operations, Support, Cyber Security, Product Management, Data & Integration, ensuring each function supports Woodbine’s overall business strategy.

· Identify and integrate emerging technologies that improve operational efficiency, customer experience, and competitive advantage.

· Represent IT strategy and performance to executive leadership, governing bodies, and external partners.

Operational Excellence

· Lead the day‑to‑day operations of technology, ensuring stable, secure, high‑performing IT services.

· Oversee infrastructure, network, cloud operations, and enterprise applications, ensuring scalability and reliability.

· Own and manage the technology budget, ensuring effective investment and cost optimization.

· Establish strong governance frameworks to guide decision‑making, prioritization, and risk management.

· Monitor and optimize IT service delivery performance with a customer‑centric mindset.

Cyber Security & Risk Management

· Build, implement, and evolve a multi‑year Cyber Security Strategy aligned to NIST and industry best practices.

· Ensure robust risk management practices, including threat monitoring, incident response, and compliance.

· Champion a culture of cyber awareness across the organization.

Product Management, Data & Integration

· Mature and lead the Product Management function to maximize value from Woodbine’s core applications.

· Drive data strategy, governance, and integration initiatives to enhance business intelligence and decision‑making.

· Partner with business units to ensure digital products and data capabilities support operational and strategic goals.

Stakeholder Partnership & Business Integration

· Act as a trusted advisor to senior leaders and business stakeholders, helping them define requirements and prioritize initiatives.

· Collaborate cross‑functionally to develop roadmaps, ensure alignment, and create clear visibility into technology plans and progress.

· Build strong relationships across the enterprise to ensure technology solutions support business outcomes.

People Leadership

· Lead and develop high‑performing teams across IT Operations, Support, Cyber Security, Product Management, and Data.

· Foster a culture of accountability, innovation, continuous improvement, and strong service orientation.

· Build organizational structures, processes, and capabilities that support current and future business needs.

Experience & Qualifications

· 10–15 years of experience in IT, including 5+ years in senior leadership roles.

· Broad technology expertise across IT Operations, Support, Cyber Security, Product Management, and Data.

· Bachelor’s degree in Computer Science, Information Systems, or related field (or equivalent experience).

· Proven experience developing and executing technology strategies aligned with business goals.

· Demonstrated success leading large teams, complex projects, and enterprise‑wide transformations.

· Strong communication, stakeholder management, and relationship‑building skills with the ability to simplify complex technical concepts.

· Experience managing technology budgets and resource planning.

· Demonstrated ability to drive innovation while maintaining operational excellence.

Personal Attributes

· Strategic thinker with strong business acumen.

· Collaborative, influential, and effective at navigating diverse stakeholder needs.

· Customer‑focused mindset with a passion for service quality.

· Leader who develops talent and builds high‑trust teams.

· Resilient, adaptable, and comfortable leading through change.

Reason for vacancy: New position

Diversity, Equity, Inclusion and Belonging

Be Yourself.

We believe differences should be valued and celebrated. By building diverse and inclusive teams, we strive to provide a more authentic and empowering work experience that unlocks the potential of our people. Regardless of race, religion, colour, national origin, sex, gender, expression, sexual orientation, age, marital status, veteran status, or disability status, we believe everyone has the right to express their ideas, ambitions, and pursue their goals with confidence and integrity. Diversity breeds innovation. We want people to think differently. Our commitment is to build a culture that welcomes everyone and leverages their unique perspectives to be a great entertainment company that shares the thrill of horseracing experiences with the world.