Technology Transformation Delivery Lead

Weekday AI; Toronto; On-site; CAD 130,000 - 160,000; Full time

Job summary

A leading technology consultancy is seeking a Technology Transformation Delivery Lead in Toronto to spearhead enterprise-scale digital initiatives. This role requires overseeing cloud modernization, application migration, and guiding cross-functional teams to ensure effective technology rollouts. Candidates should have over 10 years of experience with significant cloud and application migration expertise, along with leadership and stakeholder engagement skills. Certifications in project management are a plus.

Qualifications

• 10+ years managing enterprise technology initiatives with at least 4 years in cloud or application migration.
• Proficiency in Agile, Scrum, Waterfall, and SDLC.
• Strong understanding of technical architectures and integration points.

Responsibilities

• Define and execute delivery roadmaps for technology modernization.
• Direct end-to-end migration programs for applications, data, and infrastructure.
• Establish governance practices for tracking deliverables and risks.
• Lead collaborative efforts across engineering, cloud, data, QA, and business teams.
• Guide teams through process changes and training needs.

Skills

Leadership

Stakeholder engagement

Analytical thinking

Communication

Negotiation

Education

Bachelor's degree

PMP certification

PMI-ACP certification

Scrum Master certification

Tools

Jira

Azure DevOps

MS Project

Power BI

Job description

This role is for one of the Weekday's clients

Min Experience: 8 years

Location: Toronto

JobType: full-time

We are seeking a highly accomplished Technology Transformation Delivery Lead to spearhead enterprise-scale digital initiatives, including cloud modernization, application migration, and complex technology rollouts. This role demands a strategic leader who can bridge business objectives with technical execution, ensuring smooth delivery across multiple teams, platforms, and stakeholders. The ideal candidate thrives in dynamic environments and excels at orchestrating cross‑functional collaboration to drive impactful outcomes.

Key Responsibilities

Program Strategy & Roadmap Execution

• Define and execute multi‑phase delivery roadmaps for technology modernization and migration initiatives.
• Structure project scope, sequencing, resource allocation, and delivery milestones to ensure predictable outcomes.

Application & Cloud Migration Leadership

• Direct end‑to‑end migration programs spanning applications, data, and infrastructure.
• Partner with architects and SMEs to validate solution designs, migration strategies, and technical feasibility.

Risk, Dependency & Governance Management

• Establish governance practices for tracking deliverables, budget utilization, risks, and interdependencies.
• Implement mitigation strategies to maintain delivery continuity and avoid delays.

Stakeholder Alignment & Executive Communication

• Maintain strong communication with business leaders, engineering heads, and external partners.
• Provide outcome‑focused updates through reports, dashboards, and executive briefings.

Cross‑Functional Coordination

• Lead collaborative efforts across engineering, cloud, data, QA, cybersecurity, and business operations teams.
• Champion Agile, Scrum, or hybrid methodologies to enable efficient and adaptive delivery.

Change Enablement & Adoption

• Guide organizational teams through process changes, training needs, and adoption challenges.
• Support rollout planning, readiness assessments, and transition‑to‑operations strategies.

Vendor & Partner Oversight

• Manage relationships with implementation partners and technology vendors to ensure alignment on deliverables and timelines.

Quality, Security & Compliance Assurance

• Ensure that all technology deployments adhere to compliance mandates, security standards, and enterprise quality benchmarks.

Required Qualifications

• Experience: 10+ years overseeing enterprise technology initiatives, with at least 4 years dedicated to cloud, data, or application migration programs.
• Technical Acumen: Ability to understand technical architectures, cloud environments, integration touchpoints, and solution dependencies.
• Methodologies: Proficiency with Agile, Scrum, Waterfall, SDLC, and hybrid delivery frameworks.
• Tools: Hands‑on experience with Jira, Azure DevOps, MS Project, and modern reporting dashboards (Power BI or similar).
• Soft Skills: Exceptional leadership, stakeholder engagement, communication, analytical thinking, and negotiation capabilities.
• Education: Bachelor’s degree required. Certifications such as PMP, PMI‑ACP, or Scrum Master are an advantage.