Senior Delivery Manager – Infrastructure Managed Services & IT Operations

Experience

12+ Years

Location

Canada/Hybrid

Role Summary:

We are seeking a Senior Delivery Manager to lead the end-to-end delivery of a large-scale infrastructure separation, modernization, and operational transformation program for our client. This role is not deeply hands-on technical, but requires strong understanding of enterprise IT infrastructure, cloud, security, and end-user services to effectively translate business and customer requirements into executable delivery plans for engineering teams.

The Delivery Manager will act as the primary interface between the client, internal engineering teams, ensuring delivery commitments, timelines, governance, and operational stability are met. This is a high-visibility onsite/hybrid role supporting operations and business stakeholders.

Key responsibilities:

Program & Delivery Management:

Own end-to-end managing of infrastructure and IT operations initiatives, ensuring scope, schedule, cost, and quality targets are met

Lead delivery of full separation from existing shared MSP infrastructure, including networks, Active Directory, servers, storage, and security

Manage transition from incumbent MSP, stabilization phase, and move to long-term steady-state operations

Develop and track integrated delivery plans, milestones, dependencies, risks, and mitigation strategies

Ensure consistent execution across multiple parallel workstreams (cloud, security, network, end-user, operations)

Customer & Stakeholder Management:

Serve as the primary customer-facing delivery lead

Understand business and regulatory requirements and translate them into clear delivery expectations

Facilitate regular governance forums, status reviews, and executive readouts

Drive alignment between Client IT, business stakeholders, engineering teams, and third-party vendors

Proactively manage escalations, risks, and cross-team dependencies

Infrastructure & Cloud Transformation, Network, Security/Compliance Oversight:

Oversee delivery of a standalone client-owned infrastructure model with clear governance and ownership

Ensure implementation of cloud governance, tagging, FinOps alignment, identity controls, and automation standards

Drive proactive monitoring and alerting across servers, network, security, endpoints, and cloud services

Coordinate deployment of enterprise-grade security services, including SOC/MDR, SIEM, EDR, and vulnerability management

Ensure infrastructure meets regulatory, audit, and security posture expectations

Oversee multi-office IT support, including connectivity, LAN rooms, printers, scanners, and WiFi management

Ensure consistent and reliable end-user services, including onboarding/offboarding, device lifecycle management, helpdesk, and in-person support

Ensure Microsoft 365 security and compliance controls are implemented (Backups, Retention, Legal Hold, DLP, MFA, Conditional Access)

Documentation & Operational Readiness:

Ensure development of operational documentation, including Runbooks, SOPs, Architecture and network diagrams, Disaster recovery and business continuity plans, Asset inventories

Drive operational readiness, handover, and continuous improvement post-transition

Required Qualifications:

12+ years of experience in IT delivery management, infrastructure program management, or IT operations leadership

Proven experience managing large-scale infrastructure transformation or MSP transition programs

Strong understanding of:

Enterprise IT infrastructure (Networks, AD, Servers, Storage)

Cloud platforms (Azure preferred)

Security and compliance concepts

End-user computing and IT operations

Excellent customer-facing, communication, and stakeholder management skills

Strong ability to coordinate cross-functional engineering teams with Onsite & Offshore model

Experience working in regulated or compliance-driven environments with Insurance domain is a plus

Comfortable working onsite and engaging directly with business and IT stakeholders

Desired Skills & Attributes

Strong delivery mindset with focus on outcomes, accountability, and operational stability

Ability to balance strategic direction with day-to-day execution

Organized, structured, and detail-oriented

Calm under pressure; effective at risk and issue management

Experience with cloud-first operating models and modern IT service delivery

Experience handling onsite and offshore

… more