About the role

What will you do at Hillsborough County Clerk of Circuit Court & Comptroller?

Location: Remote (on-site emergency availability required)

Employment Type: Independent Contractor (LLC)

Experience Level: Senior (7+ years)

Salary: $72-$82/hr.

About the Role

We are seeking a highly skilled Senior DevOps Engineer to provide senior-level

systems administration and Azure platform support. This hands-on role is

approximately 75% traditional Windows Systems Administration and operational

support and 25% troubleshooting and support for a custom Azure-native messaging

platform. The ideal contractor is a strong senior systems administrator with

deep Microsoft enterprise skills, Azure troubleshooting, scripting and

automation experience, strong customer service, and the ability to own complex

incidents through resolution. This is not intended to be a pure DevOps

platform-engineering role.

Key Responsibilities

* Administer and support Windows Server environments, including configuration,
patching, performance monitoring, troubleshooting, security hardening, and
operational improvement.
* Manage Microsoft Entra ID and Active Directory, including hybrid identity,
Exchange Hybrid, Microsoft Teams and eDiscovery, users, groups, access
controls, and permissions.
* Administer DNS/Infoblox, SSL/TLS certificates, privileged access functions,
enterprise FTP services, file shares, and NTFS permissions.
* Respond to service requests and incidents, serve as an escalation point for
complex infrastructure issues, and support after-hours maintenance, on-call
activities, and emergency operations when required.
* Support and troubleshoot a custom Azure-native messaging solution through
log/telemetry analysis, root-cause analysis, configuration review, deployment
troubleshooting, and reliability improvements.
* Troubleshoot Azure Service Bus, API Management, Azure Functions or similar
compute services, Cosmos DB or Azure SQL, Key Vault, Managed Identity/RBAC,
and Azure networking for PaaS services.
* Use PowerShell, Python, Terraform/Terragrunt, Git/GitHub, C#, Azure Monitor,
Log Analytics, Application Insights, KQL, and approved AI-assisted
engineering tools for automation, infrastructure-as-code, validation,
observability, troubleshooting, refactoring, and documentation.
Required Qualifications
* 7+ years of experience in systems administration, infrastructure engineering,
or enterprise IT operations with demonstrated senior-level technical
ownership and problem-solving skills.
* Strong hands-on Windows Server administration experience in an enterprise
environment, including performance, security, patching, troubleshooting, and
core infrastructure services.
* Strong experience with Microsoft Entra ID, Active Directory, hybrid identity,
Exchange Hybrid, Microsoft Teams/eDiscovery, DNS, certificate management,
access controls, and file permissions.
* Strong PowerShell scripting and operational automation experience; experience
using Python for administration, API checks, validation, reporting, log
analysis, or repeatable troubleshooting workflows.
* Experience supporting Microsoft Azure environments and troubleshooting
Azure-hosted applications/services, including platform configuration,
deployments, messaging, identity, and monitoring.
* Working experience with Terraform or Terragrunt and Git/GitHub; strong
customer-facing support and cross-team collaboration skills; must be
available on-site during emergencies.

Preferred Qualifications

* Experience with Azure Government (AzureUSGovernment), Azure PaaS networking,
Azure observability, and integration/message-flow troubleshooting.
* Ability to read, troubleshoot, and make targeted corrections to C#/.NET and
Python code; experience with Kubernetes or containerized workloads is
beneficial but not required.
* Experience leveraging approved generative AI or AI-assisted development tools
for DevOps scripting, Terraform/IaC, debugging, root-cause and log/KQL
analysis, refactoring, deployment validation, and runbook creation; ability
to validate AI-generated output and safeguard credentials and sensitive
information.
* Relevant certifications such as Microsoft Windows Server Hybrid
Administrator, Azure Administrator, Azure Solutions Architect, Azure DevOps
Engineer, or HashiCorp Terraform Associate.
* Bachelor's degree in Information Systems, Computer Science, or a related
field preferred; equivalent relevant experience accepted. Operational
documentation and runbook experience is also preferred.
Why Contract with Us?
* Contract is with local government entity
* Serve in a high-impact senior technical role supporting mission-critical
public services across traditional Microsoft enterprise technologies and
modern Azure-native services.
* Support a strategic Azure-hosted messaging platform while strengthening
automation, reliability, and troubleshooting capabilities through an
independent contractor engagement with competitive hourly compensation.

Which skills does this role require?

Windows Server AdministrationPowerShellActive DirectoryMicrosoft Entra IDAzure Service BusGitGitHubSystems AdministrationInfrastructure EngineeringSecurity HardeningTerragruntAPI ManagementCosmos DBAzure SQLKey VaultLog AnalyticsApplication InsightsInfrastructure-as-CodeHybrid IdentityDNSInfobloxSSL/TLSNTFSC#SQLLLMs

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