Head of IT Service Delivery

The Head of Managed IT Services is a hands-on operational leader responsible for managing external IT service delivery across desktop support, server support, and M365 tenancy services. This role addresses critical technical capability gaps that currently impact service delivery and requires someone who lives in the operations daily managing service delivery, optimizing tools, solving technical problems, and ensuring SLA compliance. This is fundamentally an operational role where 80%+ of time is spent in day-to-day execution and technical problem-solving. This leader will be deeply engaged in the operational aspects of service delivery, from managing major incidents personally to optimizing technology platforms hands-on. The role requires expertise across the MSP technology stack including Microsoft M365/O365, Threat locker, Acronis Cyber Protect, Datto RMM, Autotask, and Cloudflare, with the expectation that the incumbent will actively work with these platforms to drive service excellence and operational maturity. This person will be primarily focused on operational execution, technical escalation handling, ITIL process implementation, and building operational capability within the team. This is a role for someone who has lived in MSP operations, understands the challenges intimately, and finds satisfaction in operational excellence and technical problem-solving rather than strategic planning meetings.Education Bachelor's degree in Information Technology, Computer Science, or related fieldITIL Foundation certification required; ITIL Expert/Practitioner highly desirableMicrosoft certifications (M365, Azure) requiredAdditional security certifications (Security+, CISSP) highly desirable Experience 10-15 years in IT service delivery with significant MSP operational experienceMinimum 5 years in hands-on technical leadership roles with direct operational responsibilityProven track record managing internal IT services at scale (800+ users)Extensive experience with MSP operations and service delivery in complex environmentsMust have "lived in the trenches" of day-to-day operations, not just managed from distanceExperience implementing ITIL/ITSM processes in real operational environmentsTrack record of measurably improving SLA performance and operational metrics Essential Technical Expertise (Must-Have - Deep Hands-On Capability Required or have used an equivalent technology) Microsoft 365/O365: Expert-level administration across all workloads including Exchange, SharePoint, Teams, Intune, Azure AD, security and compliance featuresThreat locker: Advanced proficiency in endpoint security management, application whitelisting, and security policy enforcementDatto RMM: Deep operational knowledge including automation capabilities, monitoring configuration, and scriptingAutotask PSA: Expert workflow optimization, configuration management, and automation setupCloudflare: Network security configuration, DNS management, and web application firewall managementWindows Server: Advanced administration including AD, Group Policy, DNS, DHCP, virtualization platformsAzure: Infrastructure management, hybrid cloud services, and security configurationPowerShell: Advanced scripting and automation expertise for Windows environmentsITIL/ITSM: Practical implementation experience, not just theoretical knowledgeNetwork Infrastructure: Routing, switching, VPN configuration, firewall management, network troubleshootingSecurity & Compliance: Patch management, vulnerability management, backup/disaster recovery, incident responseWork Setup:Shift: DayshiftSetup: HybridLocation: Cebu CityBy Applying, you give consent to collect, store, and/or process personal and/or sensitive information for the purpose of recruitment and employment may it be internal to Cobden & Carter International and/or to its clients.