Director, Enterprise Applications

Job Type: Full Time, Permanent

Salary Range: $143,837-$160,000

We Provide

• Full benefits package for full-time employees
• Retirement savings plan
• Exciting, supportive and fun work environment
• Family and friends discounts on travel, tech, food, beverage, and fitness
• Development and training opportunities

The Position

The Director, Enterprise Applications is responsible for leading the strategy, lifecycle, and continuous improvement of Gateway’s core enterprise application portfolio. This role oversees a team of product managers and technical specialists accountable for business-critical platforms including Financial Systems, HRIS, Gaming Management Systems (GMS), and other operational and corporate applications.

This leader will act as the primary bridge between the business and technology, ensuring applications deliver measurable value, align with enterprise strategy, and evolve in step with regulatory, operational, and business needs.

Key Responsibilities 

Product Strategy & Portfolio Ownership

• Own the enterprise product strategy for Gateway’s core application portfolio, including financial, HR, gaming, and operational systems.
• Define and maintain product roadmaps aligned with business priorities, operational requirements, and technology standards.
• Balance enhancement demand, technical health, regulatory requirements, and vendor roadmaps across multiple platforms.
• Establish clear product vision, outcomes, and success measures for each application domain.

Product Delivery & Lifecycle Management

• Lead the full product lifecycle from intake and prioritization through delivery, adoption, and optimization.
• Partner with Architecture, Security, and IT Operations to ensure scalable, secure, and supportable solutions.
• Drive adoption, change readiness, and continuous improvement post?implementation.

Business & Stakeholder Engagement

• Serve as a senior point of accountability for business leaders across Finance, Human Resources, Casino Operations, Compliance, and corporate functions.
• Facilitate structured intake and prioritization of business demands using transparent, outcome?based decisioning.
• Translate business needs into actionable product requirements and trade?off recommendations.
• Communicate product roadmap status, risks, and value realization to executives and senior leadership.

Vendor & Platform Management

• Oversee strategic vendor relationships for enterprise platforms, including product roadmap alignment and performance management.
• Partner with Procurement and Legal on contract negotiations, renewals, and cost optimization.
• Ensure vendor solutions meet Gateway’s operational, regulatory, security, and scalability requirements.

People Leadership & Capability Development

• Lead, coach, and develop a team of Product Managers across multiple application domains.
• Establish consistent product management practices, standards, and governance.
• Build strong domain expertise within the team while maintaining enterprise alignment.
• Support talent development, succession planning, and performance management.

What You Bring  

• 10+ years of experience in technology, product management, or enterprise application leadership is required.
• 5+ years in a senior leadership role managing product managers or application portfolios is required.
• Proven experience owning and evolving enterprise platforms (Finance, HRIS, ERP, or regulated industry systems) is necessary.
• Strong stakeholder management skills with demonstrated executive level communication are required.
• Exposure to modern product management practices is required.
• Familiarity with Gaming Management Systems (GMS) or other mission critical operational platforms is preferred.
• Experience balancing competing priorities across complex, multi business environments is preferred.
• Experience in gaming, hospitality, retail, healthcare, or other highly regulated industries is preferred.
• Experience operating in a multi site, 24/7 environment is preferred.

Who We Are

Gateway Casinos & Entertainment Limited (“Gateway”) is one of the largest and most diversified gaming and entertainment companies in Canada with 31 gaming properties in British Columbia, Ontario and Alberta. Across its entire portfolio, Gateway currently employs approximately 7,200 people and features approximately 391 table games (including 31 poker tables), 14,288 slots, 81 food and beverage outlets and 564 hotel rooms.

Gateway has been in the business of gaming and entertainment in Canada for more than thirty years and continues to evolve and expand its renowned offerings, including developing casino and restaurant brands. The Gateway to Your Future starts with us.

Gateway celebrates and empowers our team members, who make it all possible. A career at Gateway means working with great people, being recognized for your unique contribution and career advancement opportunities across our 31 locations. Our employees thrive with ongoing training and leadership programs while working in a dynamic and fun environment. See for yourself what it’s like to be on a team that values your vision, skill and energy.

This job posting is for an existing vacancy. 

Gateway does not utilize any form of artificial intelligence (AI) in the screening, assessment, or selection of applicants.