Senior Technical Specialist

We are seeking a highly skilled Senior Technical Specialist to serve as the most senior hands-on technical role within the business. The post-holder will be responsible for overseeing the delivery of professional services and project work across the client base, acting as the final point of technical escalation beyond the service desk and second-line support teams, and supporting the Directors with pre-sales scoping, technical proposals and client advisory services.

The role requires a senior engineer with deep hands-on expertise across Microsoft 365, Entra ID, Intune and Azure; who has led engineering teams in a managed-service environment; and who has delivered security, compliance and business-continuity programmes for regulated or listed clients to recognized standards such as ISO 27001 and Cyber Essentials Plus. The post-holder will plan and run tenant onboarding and security-hardening engagements, lead migrations and infrastructure projects end to end, and raise the technical capability of the wider team through mentoring and documented standards.

Key Responsibilities

Professional services and project delivery

• Scope, plan and deliver client projects end to end, including Microsoft 365 and Azure migrations, tenant consolidations, identity and device management rollouts, and backup and disaster-recovery implementations, owning cost, time and quality outcomes.
• Produce statements of work, technical implementation plans, project plans, risk registers and change-control documentation to IRIS 365 standards, and present them to client stakeholders for approval.
• Lead multi-site and multi-tenant projects, coordinating internal engineers, client staff and third-party vendors to keep delivery on schedule and within budget.
• Maintain accurate time recording, project status reporting and billing information in Autotask PSA for all professional-services work.

Tenant onboarding and security hardening

• Plan and execute the onboarding of new client tenants into IRIS 365 management, including GDAP relationship setup, baseline configuration, documentation in IT Glue and handover to the service desk.
• Implement and maintain Zero Trust security controls in Microsoft 365 and Entra ID, including Conditional Access, multi-factor authentication, Privileged Identity Management (PIM), Data Loss Prevention (DLP), Microsoft Purview and Defender policies.
• Deploy and manage Microsoft Intune and Windows Autopilot device-management baselines, and maintain configuration standards through Inforcer across the managed tenant estate.
• Conduct tenant, licensing and security-posture audits against CIS Controls v8.1, and translate findings into prioritized remediation roadmaps for clients.
• Implement, maintain and test business-continuity and disaster-recovery solutions, including Veeam Backup for Microsoft 365 and Azure-based replication, and verify recoverability on a scheduled basis.

Third-line escalation and incident response

• Act as the senior technical escalation point for complex incidents across Microsoft 365, Entra ID, Azure, Intune, networking (FortiGate) and backup platforms that cannot be resolved by first- or second-line engineers.
• Lead the technical response to security incidents and major outages affecting client tenants, including containment, root-cause analysis, client communication and post-incident reporting.
• Liaise with Microsoft, Veeam, Fortinet and other vendor support channels on behalf of clients where escalation beyond IRIS 365 is required.
• Participate in the out-of-hours escalation rota as required to support the follow-the-sun service model.

Pre-sales, client advisory and governance

• Support the Directors in pre-sales engagements by assessing client requirements, scoping technical solutions, estimating effort and producing technical proposals.
• Provide vCIO-style advisory to client leadership teams on cloud strategy, cyber-security posture, AI readiness and governance (including Microsoft 365 Copilot), and technology roadmaps.
• Contribute to client security and compliance reviews, regulatory questionnaires and audit evidence packs, with particular attention to regulated clients and the Cayman Islands Data Protection Act.
• Build and maintain relationships with strategic client accounts, attending service reviews and acting as a trusted technical adviser.

Technical leadership and continuous improvement

• Mentor and develop engineers in the Cayman and Manila teams, including structured training plans, technical reviews and knowledge-sharing sessions.
• Define, document and maintain IRIS 365 technical standards, runbooks and knowledge-base articles in IT Glue, and ensure the service desk can operate them consistently.
• Evaluate new Microsoft and partner technologies and recommend improvements to the IRIS 365 service catalogue, toolchain and operating model.
• Contribute to the development and maintenance of IRIS 365's own information-security management practices and any future ISO 27001 or equivalent certification programme

Qualifications

• Bachelor's degree (or higher) in Information Systems, Computer Science, Business Information Systems or a closely related discipline, or equivalent demonstrable professional experience.
• A recognized management or leadership qualification (for example CMI Level 5 or equivalent), or demonstrable evidence of formal people-management training.
• A current Microsoft certification in Microsoft 365, Azure or security (fundamentals level or above), with a willingness to achieve associate- or expert-level Microsoft certification within the first 12 months.
• A minimum of eight years' progressive experience in IT infrastructure and services, of which at least three years have been in a senior, lead or head-of-function role within a managed service provider (MSP).
• Proven experience as the senior technical escalation point for second-, third- and fourth-line engineering teams supporting multiple client environments.
• Hands-on implementation and administration experience across Microsoft 365, Entra ID, Microsoft Intune, Windows Autopilot and Microsoft Azure, including Conditional Access, Privileged Identity Management and Data Loss Prevention
• Experience implementing and delivering Zero Trust security programmes and leading clients through recognized security or quality certifications such as ISO 27001, ISO 9001 or Cyber Essentials Plus.
• Experience implementing and supporting business-continuity and disaster-recovery solutions, including Veeam backup and Azure-based replication.
• Demonstrable ownership of technical project delivery against cost, time and quality objectives, including multi-site or multi-tenant programmes.
• Experience advising board-level or C-suite stakeholders at regulated, listed or financial-services organizations on technology strategy, cyber-security and risk.
• Experience managing a team of engineers and holding accountability for service levels, budgets and customer-satisfaction outcomes.
• Working knowledge of professional-services automation and remote-monitoring tooling used in MSPs (for example Autotask PSA, Datto RMM, Halo PSA, KaseyaOne) and of ITIL-aligned service management.
• Vendor certifications relevant to the IRIS 365 stack, such as Veeam Technical Sales Professional (VMTSP), Cisco CCNA or Fortinet NSE.
• Experience deploying and governing Microsoft 365 Copilot or other enterprise AI tooling, including readiness audits, permission boundaries and data-security baselines.
• Experience with Inforcer or similar multi-tenant Microsoft 365 configuration-management platforms, and with Apple Business Manager or third-party MDM.
• Experience building Power BI reporting for executive risk, service or operational visibility.
• Familiarity with GDPR or the Cayman Islands Data Protection Act and with the cybersecurity expectations of financial-services regulators.
• Experience of fractional or virtual CIO engagements and commercial partnership development within an MSP.

Working conditions: The role is based at the IRIS 365 office in George Town with regular travel to client sites across Grand Cayman. The post-holder must be able to work occasional evenings and weekends for planned maintenance windows, migrations and incident response, and to participate in the escalation rota supporting the follow-the-sun service model with the Manila team. A clean police clearance certificate, satisfactory references and a successful background check are conditions of employment, reflecting the regulated environments in which IRIS 365 operates. Statutory benefits

Those interested and qualified, please send your resume and cover letter at [email protected] by November 13, 2026