Technical Program Manager

Our Customer is looking for a Senior Technical Program Manager to lead two connected migration workstreams within Mosaic, a strategic initiative focused on technology modernization and risk reduction.

This is a delivery leadership role for a technically complex and security-sensitive program, rather than a generic coordination position. The role covers the full delivery lifecycle, including analysis, migration planning, dependency management, operational readiness, controlled rollout, and execution across multiple technical and business teams.

Project Overview:

Mosaic brings together risk-reduction and modernization initiatives across identity, access, infrastructure, and audit readiness.

As a Senior Technical Program Manager, you will focus on two connected migration workstreams that require close collaboration between engineering, security, infrastructure, platform, and business teams.

You will be responsible for turning complex technical objectives into a clear delivery structure, driving execution, managing dependencies and risks, and ensuring that migrations are delivered in a controlled and operationally ready way.

Responsibilities:

Shape the Program

• Translate the two migration objectives into one executable program structure with clear workstreams, milestones, owners, assumptions, and success criteria.

• Define clear scope boundaries and responsibilities between the TPM, engineering teams, security, platform teams, O365 administrators, and business stakeholders.

• Create and maintain an integrated roadmap and identify the critical path.

• Identify where additional staffing, technical decisions, or leadership support are required to keep delivery moving safely.

Drive End-to-End Delivery

• Own the integrated delivery plan from initial analysis through migration design, execution readiness, rollout, and closure.

• Coordinate participating technical teams and external contributors.

• Ensure migration activities include business readiness, communications, cutover planning, fallback scenarios, and post-migration validation.

• Track progress and ensure delivery remains aligned with program objectives.

Manage Risks, Issues, and Dependencies

• Maintain a transparent view of risks, actions, issues, dependencies, and decisions across both migration workstreams.

• Identify delivery blockers early and drive them toward resolution.

• Manage dependencies related to device strategy, regional rollout constraints, tenant dependencies, identity prerequisites, and team capacity.

• Escalate issues with clear recommendations and follow through until blockers are resolved.

Establish Program Governance

• Set up lightweight but rigorous governance appropriate for a security- and migration-focused program.

• Own the integrated plan, RAID log, dependency map, decision log, stakeholder map, and executive status reporting.

• Establish migration-readiness checkpoints and ensure key decisions are made on time.

• Keep governance focused on delivery discipline and effective decision-making rather than administrative overhead.

Apply Technical Fluency

• Work closely with identity, endpoint, infrastructure, security, and platform specialists.

• Understand the delivery implications of managed-device rollouts, AWS-hosted VDI access patterns, Entra ID and Active Directory dependencies, O365 administration, access governance, and legacy-state retirement.

• Challenge migration sequencing and identify hidden technical prerequisites.

• Translate technical constraints into clear business and program implications to support timely decision-making.

Requirements:

• Strong experience as a Technical Program Manager, Senior Program Manager, or similar delivery leadership role.

• Proven experience leading multi-team migration or transformation programs in complex technology environments.

• Experience with identity, access, endpoint, infrastructure, or platform-related migrations.

• Experience driving initiatives that combine technical migration work with stakeholder management, operational readiness, and controlled rollout.

• Ability to work credibly with senior engineers, architects, security stakeholders, and business sponsors.

• Strong experience managing risks, dependencies, scope trade-offs, issues, and cross-team conflicts.

• Proven ability to drive delivery rather than focusing solely on PM frameworks and reporting.

• Strong written and verbal communication skills, including executive reporting and decision framing.

• Strong organizational and problem-solving skills.

• Ability to understand complex technical dependencies and translate them into business and delivery implications.

• Fluent English.

Nice to have:

• Experience with Microsoft Entra ID / Azure AD.

• Experience with Active Directory.

• Experience with Microsoft 365 / O365.

• Experience with AWS-hosted VDI environments.

• Experience with endpoint/device management.

• Experience working in security-sensitive or highly regulated environments.

Important:

Business travel to Toronto, Canada is required.

Why join?

This is an opportunity to take ownership of a high-impact technology transformation program, working across engineering, security, infrastructure, identity, and business teams. The role offers significant visibility and influence over how complex migration initiatives are planned, governed, and delivered.