Apply for Associate Director - Digital Enablement

Our enterprise client — a large, complex institution operating at the intersection of research, education, and administration — is seeking a strategic senior leader to join their Digital Enablement team as Associate Director. This is a newly created, full-time permanent role that reflects a deliberate investment in maturing the institution's application portfolio management capability.

Reporting to the Director, Digital Enablement, the Associate Director will assume enterprise-wide accountability for a broad, multi-layered application portfolio, leading through subordinate Senior Managers across several lines of service. This is a role for a seasoned leader who can operate at both the strategic and operational level — someone who brings genuine ownership of application lifecycle governance, not simply project delivery experience.

The successful candidate will drive meaningful portfolio modernization, rationalization, and sustainability while navigating a large and distributed stakeholder environment with skill, credibility, and political acuity.

What We’re Looking For

This role is best suited to candidates who can demonstrate:

• True enterprise ownership of an application portfolio — not just project delivery. You have been accountable for strategy, financial management, vendor governance, and lifecycle outcomes across a complex, multi-system environment.
• Leadership through modernization and organizational change. You have successfully led rationalization and modernization programs at scale, and you know how to bring people through ambiguity.
• Experience engaging senior stakeholders across large institutions. You are comfortable operating in complex, multi-stakeholder environments and have built credibility with executive audiences.
• People leadership depth. You lead through other leaders, developing capability, building resilience, and creating conditions for high-performing teams.
• Financial accountability. You have held meaningful budget responsibility — not just input into planning — including forecasting, expenditure oversight, and resource allocation.

Candidates who are primarily technical specialists, hands-on delivery leads, or who lack clear accountability for strategy and governance are unlikely to be a strong fit for this position.

Key Responsibilities

Portfolio Strategy & Governance

• Lead the ongoing evolution of the application portfolio toward increased agility, scalability, and innovation — supporting adoption of modern delivery and operating models.
• Conduct portfolio-level assessments of application fitness, sustainability, cost, and risk, identifying opportunities for rationalization, modernization, and benefits realization.
• Define, implement, and continuously improve enterprise application lifecycle management practices in partnership with the Director, aligned with industry best practices.
• Establish and mature product management disciplines across the portfolio, including roadmap governance, performance metrics, and executive-level reporting.

People Leadership & Capability Development

• Lead through multiple Senior Managers, providing strategic direction, coaching, and accountability across several lines of service.
• Develop strategies to support staff engagement, workforce resilience, and capability development, addressing skill gaps across the portfolio.
• Develop leadership strength in functional areas by coaching reporting leaders and modeling valued leadership behaviours.
• Provide career development guidance and create meaningful development plans for staff.

Vendor & Financial Oversight

• Oversee relationships with major vendors and service providers, ensuring services are cost-effective, meet performance and contractual commitments, and align with institutional priorities.
• Provide financial leadership for the portfolio including budget planning, forecasting, expenditure oversight, and resource allocation.
• Source, negotiate, and allocate financial, physical, and human resources to support major programs.

Risk, Security & Compliance

• Serve as a subject matter expert ensuring application services comply with institutional requirements for privacy, security, accessibility, and applicable legislation.
• Partner with privacy and security leaders to ensure enterprise applications are designed, operated, and governed to mitigate risk and protect institutional and personal information.
• Provide strategic oversight of application operations, establishing standards for reliable production performance, secure release management, and sustainable deployment practices.

Innovation & Strategic Partnerships

• Collaborate with the Director to design and sustain an innovation framework enabling responsible evaluation and adoption of emerging technologies.
• Build and maintain influential relationships with senior leaders across the institution and the broader IT community.
• Anticipate technology trends and assess their impact on institutional operations and strategic goals.

Qualifications

Required

• Post-graduate degree in a relevant field (Computer Science, Information Technology, Business Administration, or equivalent).
• Minimum 11 years of related experience, including at least 5 years of managerial experience and 4 years of specialized experience in the design and implementation of major computer systems — or an equivalent combination of education and experience.
• Demonstrated commitment to equity, diversity, and inclusion, and a genuine openness to diverse perspectives.

Preferred

• Significant senior-level experience in IT application development management and operations, including SaaS, on-premises, and COTS environments.
• Demonstrated experience in performance management, succession planning, change management, and financial management.
• Knowledge and hands-on experience with ITIL process implementation, Lean IT, agile development, and application modernization programs.
• Thorough understanding of the ICT industry landscape, ideally with exposure to large, complex institutions such as post-secondary, healthcare, or public sector organizations.
• Strong capabilities in strategic planning, risk management, business process improvement, and continuous improvement.
• Effective skills in facilitation, negotiation, conflict resolution, stakeholder engagement, and team development.

Affinity Earn:

Know someone who’s great for this, or any of our open roles? Earn up to $4,000/year for each successful referral through Affinity Earn. You can also earn up to $50,000 for helping us find new clients. Learn about our referral program at https://affinity-group.ca/earn/ or browse our jobs & follow us at https://www.linkedin.com/company/affinity-staffing/jobs/

About Affinity: 

Affinity Group is a technology and business consulting and services company. We believe in creating long term relationships between clients and consultants that foster a mutually beneficial partnership. Affinity is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. All employment is decided on the basis of qualifications, merit and business need.

For more information on Affinity, please visit www.affinity-group.ca

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Job Number: 13590