Director, Technology Strategy & Transformation

Location: Toronto, Ontario

Our client is a well-established investment management firm specializing in commercial real estate, with a strong track record of delivering consistent, risk-adjusted returns to institutional and private investors. The organization operates across multiple investment strategies and is known for its disciplined approach, long-term partnerships, and continued growth.
As the business continues to scale, there is a clear mandate to modernize how it operates—through improved systems, data, workflows, and AI-driven capabilities. This role will be central to that transformation.
We are seeking a Director, Technology Strategy & Transformation to define and deliver the firm's enterprise technology vision. This individual will operate at the intersection of business strategy, process optimization, product leadership, and technical execution, ensuring that technology becomes a meaningful competitive advantage.
This is a hands-on leadership role. You will be responsible for shaping the roadmap, redesigning workflows, driving AI adoption, and ensuring systems are aligned with business needs, regulatory requirements, and long-term scalability.
Key Responsibilities
Technology Strategy & Business Alignment
• Develop and execute a multi-year technology roadmap aligned with business priorities across investment, operations, and reporting functions
• Act as a trusted advisor to senior leadership on technology, data, and AI opportunities
• Translate business needs into scalable, integrated solutions that improve efficiency, transparency, and performance
Process Optimization & Transformation
• Evaluate and redesign core business workflows using structured methodologies (e.g., Lean, Six Sigma)
• Ensure technology supports standardized, efficient processes rather than layering on inefficiencies
• Identify and eliminate manual or redundant operational steps
AI Strategy & Enablement
• Define and execute an enterprise AI roadmap across underwriting, reporting, operations, and compliance
• Identify and prioritize use cases based on business value, feasibility, and risk
• Establish governance frameworks for AI usage, including data access, privacy, and regulatory alignment
• Drive adoption through training, enablement programs, and internal champions
• Deliver measurable ROI through automation, improved accuracy, and reduced cycle times
Product & Platform Leadership
• Own product strategy, roadmap, and lifecycle management for internal platforms
• Partner with cross-functional stakeholders to define requirements and solutions
• Oversee development of systems supporting originations, portfolio management, reporting, and workflows
• Ensure all product decisions are aligned with measurable business outcomes
Technical Leadership & Execution
• Provide hands-on guidance across architecture, integrations, and system design
• Prototype solutions and support delivery teams in solving complex technical challenges
• Serve as escalation point for architecture, API, and data modeling decisions
Data Strategy & Governance
• Build and evolve the firm's data strategy, including infrastructure, integration, and analytics
• Ensure high-quality, governed, and AI-ready data across the organization
• Enable reporting and dashboards that support decision-making and performance tracking
Risk, Compliance & Operations
• Partner with Compliance, Risk, and Finance teams to ensure regulatory alignment
• Oversee cybersecurity practices, vendor relationships, and system reliability
• Ensure strong governance, documentation, and transparency across all initiatives
Team & Stakeholder Leadership
• Collaborate across business and technical teams to drive alignment and execution
• Mentor and develop talent within the technology function
• Foster a culture of accountability, curiosity, and continuous improvement

Must Have Skills:
• 8+ years of experience in technology strategy, digital transformation, consulting, or product leadership roles
• Proven track record of leading end-to-end transformation initiatives (0•1 or large-scale system/process changes)
• Strong experience in business process optimization, ideally with Lean, Six Sigma, or similar frameworks
• Ability to translate complex business requirements into scalable technology solutions
• Experience working across cross-functional stakeholders, including business, technical, and compliance teams
• Strong understanding of enterprise systems, data environments, and integrations
• Demonstrated ability to operate across both strategy and hands-on execution
• Strong communication and stakeholder management skills

Nice to Have Skills:
• Hands-on technical background (e.g., software development, architecture, or systems design)
• Experience with AI, automation, or data-driven transformation initiatives
• Familiarity with enterprise platforms such as Salesforce, Power BI, or modern data stacks
• Experience in financial services, real estate, or other regulated industries
• Experience managing external vendors, consultants, or delivery partners
• Experience building or scaling internal technology or product functions