IT Systems Administrator

About Us:

We are a growing, cutting-edge fintech startup operating in the United States insurance software industry. We leverage modern cloud technologies to build scalable software solutions that streamline operations across the insurance value chain.

As our engineering teams continue to expand, we are looking for an IT Systems Engineer to own our internal technology environment and be the first point of contact for the people who depend on it.

The Role:

As our IT Systems Engineer, you will be the primary owner of day-to-day end-user support for our internal teams, and the custodian of the systems that keep them productive. The majority of your time will be spent resolving user-facing issues across identity, email, access and devices - this is the core of the role, and doing it well is what success looks like.

Alongside that, you will maintain the infrastructure sitting behind those services, working closely with our engineering and infrastructure teams and deepening your expertise in Azure-based infrastructure and cloud security best practices.

This is a hands-on mid-level role reporting directly to the Head of Business Systems and Operations, suited to someone with solid systems administration grounding who wants ownership rather than an escalation queue.

Because we support teams across international time zones, some flexibility in working hours is needed from time to time. We are upfront about this and will walk you through what it looks like in practice during the interview process - there is no fixed standby roster.

This role is aimed at someone moving up from a support or helpdesk position into full systems administration. If you are already working at senior level, you will likely find the scope too narrow.

Responsibilities:

Primary focus - end-user support, identity and devices (majority of the role)

• Own and resolve end-user support requests end to end, including mailbox and Exchange Online issues, account access, permissions, MFA and authentication problems, and connectivity faults
• Manage user lifecycle across Microsoft Entra ID and Microsoft 365 - onboarding, offboarding, group and license management, and permissions troubleshooting
• Configure, deploy and maintain laptops and endpoint devices using Microsoft Intune
• Administer SharePoint Online and Teams access, permissions and site structure
• Support VPN access and remote connectivity for staff
• Log, track and document incidents, and escalate to the Head of Business Systems and Operations where appropriate

Secondary focus - infrastructure and systems (periodic)

• Maintain Certificate Servers and IIS, covering deployment, configuration and ongoing service management
• Manage DNS hosting and records, including Cloudflare
• Administer firewall rules, policies and configurations on our Sophos appliances
• Own backup management, scheduling and restore verification
• Monitor and manage Azure resource allocation, including App Services, SQL Databases and networking
• Contribute to internal IT projects and continuous improvement initiatives

Requirements

• Matric, plus an IT diploma or degree, or CompTIA A+ and Network+
• 2-4 years of IT support or systems administration experience
• Experience administering a Microsoft 365 tenant through the admin centers, including license and user management
• Experience working with Azure services and the Azure portal, including an understanding of cloud service models and resource management
• Proven hands-on experience administering Microsoft Entra ID
• Experience administering Microsoft Exchange Online and SharePoint Online
• Experience administering Windows Server in a cloud-hosted environment (Azure VMs), including roles and services, patching and general server management
• Strong knowledge of Windows 11 and Microsoft 365
• Solid working knowledge of networking concepts (IP, DNS, DHCP, routing)
• Practical understanding of how business firewalls work and are managed - rules and policies, NAT, port forwarding, VPN configuration and troubleshooting blocked traffic. We run Sophos, but experience on any comparable platform (Fortinet, pfSense, Cisco, SonicWall, Palo Alto, Mikrotik or similar) is equally welcome
• Working knowledge of PowerShell for user and tenant administration
• Excellent problem-solving skills and the patience to support non-technical users well
• Valid driver's license and own reliable transport

• One current associate-level Microsoft certification - MD-102 (Endpoint Administrator Associate) preferred, or AZ-104 (Azure Administrator Associate)

  If you do not hold either but can demonstrate equivalent hands-on experience across the areas above, we would still like to hear from you. We fund certification for successful candidates who join without one.

Preferred Skills:

• Microsoft Certified: Identity and Access Administrator Associate (SC-300)

• Microsoft 365 Certified: Administrator Expert (MS-102)
• Hands-on experience with Sophos firewalls specifically
• Certificate Server and IIS administration experience
• Experience with Cloudflare DNS management
• Experience working with a ticketing or ITSM platform (we will train you on ours)
• ITIL Foundation certification
• Exposure to Azure DevOps tooling and developer environment support

Benefits

• 22 Days Annual Leave | Nearly 50% more leave than most South African employers offer
• Certification Support | We fund and support your next Microsoft certification
• Flexi Hours | Core hours are 10:00 - 15:00
• Hybrid | Mandatory in-office on Monday, Wednesday and Friday, with Tuesday and Thursday worked from home
• Flexi Remote Days | 10 per year, which may be applied for against any of the mandatory in-office days
• Weekly Happy Hour | 14:00 - 15:00 on Fridays
• Company Socials | Once a month at the end of the month