Why Smiley

Smiley Technologies is a FinTech company providing technology to community banks across the US. We’re known for a people-first culture where employees are trusted to think, contribute and take ownership of meaningful work, with a strong focus on transparency, collaboration, and accountability. 

If you’re looking for an environment where your judgment matters, your contribution is valued and you can work on technology that has a real impact for our customers, Smiley could be a great fit. 

Who we’re looking for

We’re looking for an experienced IT Systems Administrator to join our System Operations team, supporting enterprise infrastructure across both internal and client environments. 

This is a hands-on infrastructure role with a strong focus on VMware, Windows Server, and Linux administration, alongside backup and recovery, infrastructure monitoring, patching, troubleshooting, and ongoing system reliability. 

You’ll work across a varied technical environment and collaborate closely with Network Operations, Cybersecurity, Platform Engineering, and other technical teams to keep critical systems available, secure, and performing effectively. The role supports both Smiley's internal infrastructure and client environments, providing exposure to a broad range of technologies and projects. 

What You’ll Be Doing

• VMware & Virtual Infrastructure - Administer and support VMware vSphere, ESXi and vCenter environments, including virtual machines, clusters, snapshots, templates, datastores, and host maintenance. 
• Windows & Linux Administration - Configure, patch, monitor and troubleshoot Windows Server and Linux systems, supporting their ongoing performance, security, and availability. 
• Core Infrastructure Services - Support Active Directory, Group Policy, DNS, certificates, service accounts, and other core infrastructure dependencies. 
• Server Hardware & Storage – Support enterprise server hardware, firmware, and storage infrastructure, helping ensure systems remain reliable, available, and properly maintained. 
• Monitoring & Reliability - Monitor infrastructure health, performance, capacity, and availability, proactively identifying and resolving potential issues. 
• Backup & Recovery - Manage enterprise backup and recovery processes, investigate failed or degraded backup jobs, and perform restore testing and recovery validation. 
• Technical Support - Provide advanced Tier 2 / 3 support for infrastructure issues, taking ownership of troubleshooting, leading root cause analysis efforts, and coordinating resolution of infrastructure incidents. 
• Automation - Use PowerShell, shell scripting and command-line tools to automate repeatable tasks, gather diagnostics and improve operational efficiency. 
• Containers & Kubernetes - Support the underlying Linux and VMware infrastructure used by container and Kubernetes environments, collaborating with Platform Engineering when required. 
• Maintenance & Security - Support patching, vulnerability remediation, firmware updates, certificate renewals, and scheduled infrastructure maintenance. 
• Business Continuity - Participate in disaster recovery exercises, scheduled maintenance, and an on-call rotation to support critical systems. 
• Documentation & Improvement - Maintain technical documentation and operational runbooks while identifying opportunities to improve reliability, security, and standardization. 
• Knowledge Sharing & Collaboration – Contribute to team standards, share technical knowledge, support cross-training efforts, and help maintain a culture of continuous learning. 

What We’re Looking For

• Associate degree in a technical field with 4 or more years of relevant experience, or an equivalent combination of education and practical experience. 
• 4+ years of enterprise systems administration experience, including strong hands-on experience with VMware vSphere, ESXi and vCenter. 
• Experience supporting production infrastructure in hybrid, multi-environment, or managed-services environments. 
• Experience administering Windows Server 2016 - 2025, including Active Directory, Group Policy, DNS, and certificates. 
• Working knowledge of Linux administration and troubleshooting. 
• Experience with enterprise backup and recovery platforms such as Veeam, Barracuda or Unitrends. 
• Experience with infrastructure monitoring, patch management, system security, and vulnerability remediation. 
• PowerShell and/or shell scripting experience. 
• Understanding of enterprise server hardware, storage, and infrastructure dependencies. 
• Foundational understanding of containers and Kubernetes - deep Kubernetes engineering experience is not required. 
• Strong communication, organization, and attention to detail, with service-oriented approach and the ability to prioritize incidents, service requests, maintenance, and project work in a fast-paced environment. 

This is a great opportunity to join Smiley Technologies at an exciting stage of growth, working on critical technology that supports community banks across the US while gaining exposure to a broad and complex enterprise infrastructure environment. 

Next steps?

After completing your application, our Talent team will review your profile and aim to provide feedback within 5 working days. 

If you have any questions about the opportunity, or would like to know further information before applying, please don’t hesitate to reach out to jdixon@sibanking.com.