Modern Workplace Expert Engineer: Microsoft 365 and AI Operations

On Direct Business Services Limited; Cape Town; On-site; ZAR 900,000 - 1,300,000; Full time

Benefits offered by this job

Uncapped annual leave

Group Life & Disability Insurance

Fitness Cash Contribution

Pension Fund Contribution

Medical Insurance Contribution

Employee Assistance Programme

Enhanced Maternity & Paternity Leave

Growth opportunities

Culture of Excellence

Job summary

On Direct Business Services Limited in Cape Town seeks a Modern-Work Expert Support Engineer (Tier 3) to deliver advanced Microsoft 365 and Entra support, escalating to Tier 2 and coordinating with project teams. The role is hybrid, requiring strong incident management, design, and automation capabilities.

You will mentor junior engineers, lead major incidents, and contribute to onboarding and service transitions, while maintaining SLA commitments and security best practices.

Qualifications

• 5+ years hands-on Microsoft cloud operations or support experience.
• Tier 3 depth in two Microsoft domains from the list (SharePoint, Endpoint, Azure Virtual Desktop, Defender, Copilot).
• Microsoft 365 and Entra administration with security troubleshooting capabilities.
• Active Microsoft credentials from the required list.

Responsibilities

• Own complex incidents and escalations through diagnosis and resolution.
• Lead technical responses to major incidents and drive root-cause analysis.
• Lead onboarding and service transition workstreams with design input and handover.
• Produce and review designs, runbooks, and change records for high-impact work.
• Use data to remove recurring failures and introduce automation with measurable benefits.
• Mentor Tier 2 engineers and improve team standards.

Skills

Microsoft 365 administration

Microsoft Entra administration

Incident management

Root-cause analysis

Mentoring

PowerShell

Microsoft Graph

Automation

Education

Microsoft 365 Certified: Copilot and Agent Administration Fundamentals (AB-900)

Microsoft 365 Certified: Endpoint Administrator Associate (MD-102)

Tools

Nerdio Manager

SharePoint Mgmt

Data Access Governance

Microsoft Defender for Cloud Apps

Azure Monitor

Log Analytics

GitHub

Azure DevOps

CI/CD

Terraform

Bicep

Copilot Studio

Job description

As a frontier partner, we grow through great people, smart tech, and teamwork between humans and AI.

We are looking for a Modern-Work Expert Support Engineer to join our team in Cape Town.

This role offers a hybrid work environment, combining remote support with close collaboration among project and specialist teams.

The Modern-Work Expert Support Engineer (T3) will deliver advanced support to customers, serving as an escalation point for Tier 2 engineers. They will collaborate with senior engineers to manage complex projects and onboarding processes while working alongside other specialized teams within Operations.

You will ensure that service level agreements are met whilst delivering reliable resolution of customer technical issues when raised via Cloud Direct support lines, Live chat, email or self-service portals.

What you'll do:

• Own complex incidents, requests and technical escalations through evidence-led diagnosis, customer communication, resolution, validation and clear handover.
• Identify risks, technical debt, optimisation opportunities and customer improvement initiatives, producing evidence-based recommendations that support both customer outcomes and service growth.
• Lead the technical response to major incidents, coordinate specialist input, protect evidence and drive root-cause analysis and corrective actions.
• Lead the technical workstream for onboarding and service transition, including technical discovery, gap assessment, design input, remediation identification, acceptance criteria, operational-readiness review and technical handover. Work with the designated project, service or transition owner.
• Produce and review technical designs, implementation plans, test plans, rollback plans, runbooks and change records for complex or high-impact work.
• Use incident, problem, alert and service-review data to remove recurring failure, improve standards and introduce approved automation with measurable benefit.
• Set technical standards and support boundaries, review Tier 2 work, coach engineers and create reusable knowledge, diagnostic and automation assets.
• Evaluate new Microsoft capabilities and managed-service tooling; assess security, supportability, licensing, cost and operational risk before adoption.
• Own escalations to Microsoft and approved vendors, including evidence gathering, reproduction, case management, challenge and technical closure.
• Act as a trusted technical advisor by translating customer goals and platform evidence into proportionate, transparent recommendations.
• Participate in the on-call rotation and maintain clear major-incident, vendor-escalation and cross-team handover procedures

What you'll need:

• At least 5 years of hands-on Microsoft cloud operations or support experience, including at least 2 years performing genuine Tier 3 work.
• Demonstrated ownership of complex incidents, root-cause analysis, technical onboarding, high-impact change and service improvement, through to a supportable outcome.
• Expert Microsoft 365 and Microsoft Entra administration, security and troubleshooting capability, including the ability to diagnose issues across multiple workload dependencies.
• Advanced knowledge of Microsoft Purview and Microsoft 365 security controls, including how identity, access, information protection and security evidence interact across Microsoft 365.
• Independent Tier 3 depth in at least two beneficial technical domains, selected from SharePoint Management, Endpoint Management, Azure Virtual Desktop, Microsoft Sentinel or Copilot and agent engineering, with working knowledge of the broader Microsoft Digital Workplace service.
• Experience designing and operating repeatable technical solutions using PowerShell, Microsoft Graph, KQL and controlled automation practices.
• Ability to lead technical customer discussions, explain trade-offs, produce recommendations and constructively challenge unsafe, unsupported or disproportionate approaches.
• Ability to mentor Tier 2 engineers, review technical work and improve team standards, while avoiding single points of dependency.

Candidates must hold 2 active and verifiable Microsoft credentials before appointment from the list below:

• Microsoft 365 Certified: Copilot and Agent Administration Fundamentals (AB-900).
• Microsoft 365 Certified: Endpoint Administrator Associate (MD-102)
• Microsoft 365 Certified: Administrator Expert (MS-102)
• Microsoft 365 Certified: AI Services Administrator Associate (AB-650)

Beneficial certifications:

AZ-140, SC-100, SC-200, SC-300, SC-400, AZ-104, AB-410 or SC-401

Highly Desirable:

• Experience and skill set outlined in the Core Operational Capability.
• Experience with Nerdio Manager for MSP, SharePoint Advanced Management, Data Access Governance, Microsoft Defender for Cloud Apps or advanced Microsoft Purview capabilities.
• Experience with Azure Monitor, Log Analytics, GitHub or Azure DevOps, CI/CD, Terraform or Bicep in controlled production environments.
• Experience with advanced Copilot Studio integrations, custom connectors, Dataverse, multi-agent solutions, Microsoft Foundry or enterprise APIs.

What do we offer you?

• Responsible Time off (uncapped annual leave)
• Group Life Cover /Disability Income Cover/ Trauma Insurance Cover (Injury / Disability)
• Fitness Cash Contribution
• Pension Fund Contribution
• Medical Insurance Contribution
• Employee Assistance Programme
• Enhanced Maternity & Paternity Leave
• Endless Growth Opportunities: We provide ample opportunities for professional development, mentoring, and advancement.
• Culture of Excellence: We foster a high-performance culture that recognizes and rewards exceptional talent.

At Cloud Direct, you're not just joining a company-you're becoming part of a team that is redefining how businesses experience cloud technology. As we push the boundaries of innovation, especially in user-centric design and AI-driven solutions, your contributions will help shape the future of our platform and the value it delivers to customers.

We believe that diversity, equity, and inclusion are essential to our success. We are committed to creating a workplace where everyone feels valued, respected, and empowered. We welcome applicants from all backgrounds and strive to build a team that reflects the diverse communities we serve. We encourage candidates of all races, ethnicities, genders, sexual orientations, ages, abilities, and socioeconomic statuses to apply!

Due to the high volume of applications received, if you have not been contacted within 4 weeks of the closing date, please consider your application unsuccessful.