Senior Service Delivery Manager

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 work streams (cloud, security, network, end-user, operations)
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, Fin Ops 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 Security and compliance concepts
Strong understanding of 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

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