Inclusively is partnering with an insurance technology company to hire a System Administrator. **Please note: this role is NOT an internal position with Inclusively but with the partner company.**

ABOUT INCLUSIVELY

Inclusively is a digital tech platform that empowers job seekers with disabilities, caregivers, and veterans by using Success Enablers–accommodations and personalized workplace modifications that help all job seekers reach their full potential and excel. This includes all disabilities under the ADA, including mental health conditions (e.g. anxiety, depression, PTSD), chronic illnesses (e.g. diabetes, Long COVID), and neurodivergence (e.g. autism, ADHD).

Create your profile, select Success Enablers, and connect to jobs from our partnered employers who are committed to creating diverse and inclusive teams. When registering, you must acknowledge that this platform is for people with disabilities, caregivers, and veterans. However, Inclusively does not require candidates to disclose their specific disability to join the platform.

Position Overview

We're seeking an experienced and highly skilled Systems Administrator to join our infrastructure team. In this role, you will support and maintain hybrid infrastructure spanning colocation data centers and cloud environments, including Azure and Google Cloud Platform (GCP).

You will be a key contributor to the day-to-day operation and continuous improvement of our infrastructure — responsible for Windows Server administration, virtual machine lifecycle management, cloud platform operations, patch management, monitoring and observability, and infrastructure automation. You will help ensure our systems remain reliable, secure, and operationally efficient while identifying opportunities to eliminate repetitive manual work and turn recurring incidents into permanent solutions.

The ideal candidate is a self-sufficient infrastructure operator with strong Windows Server experience, a solid understanding of hybrid cloud environments, strong troubleshooting skills, and an automation mindset. This is an individual contributor role focused on execution, reliability, operational excellence, and continuous improvement.

What You’ll Do

• Administer and support Windows Server environments across colocation and cloud infrastructure, including provisioning, configuration, upgrades, patching, and day-to-day operational support
• Manage virtual machine lifecycles, including provisioning, resource management, right-sizing, operational health, and decommissioning across on-premises and cloud environments
• Support and maintain infrastructure across colocation facilities and cloud environments, including Azure and GCP
• Manage cloud resources including virtual machines, storage, networking, and core platform services
• Perform system upgrades, patching, and backup operations across cloud and on-premises environments
• Execute and maintain patch management processes across Windows Server environments, including maintenance windows, patching cadences, and pre- and post-patch validation
• Respond to security vulnerability findings by triaging, scheduling, and remediating identified exposures in partnership with security teams
• Monitor system performance, availability, and capacity across cloud and on-premises environments using monitoring and observability platforms
• Build, tune, and maintain monitors, alerts, and dashboards to improve signal quality, reduce noise, and identify issues before they become incidents
• Respond to infrastructure alerts and incidents, perform root cause analysis, and implement corrective actions
• Identify recurring operational issues and use automation or permanent fixes to improve system reliability
• Build and maintain automation for recurring operational processes such as patching, VM provisioning, health checks, remediation, and reporting
• Develop scripts and automated solutions using PowerShell, Python, Ansible, or similar technologies to eliminate repetitive operational tasks
• Integrate automation with monitoring and observability platforms to support automated responses, proactive checks, and self-healing workflows
• Support Infrastructure as Code practices for repeatable and consistent environment provisioning
• Create and maintain technical documentation, operational runbooks, and procedural guides
• Collaborate with development, cloud engineering, IT support, and operations teams to support system integration and service delivery
• Communicate clearly regarding system status, incident updates, and project progress
• Contribute to post-incident reviews and continuous improvement of operational processes

We’re looking for someone who:

Your experience should include some or all of the following:

• Bachelor's degree in Engineering, Computer Science, or a related field, or equivalent practical experience
• 3–6 years of experience in systems administration, infrastructure operations, or cloud operations
• Strong hands-on experience administering Windows Server environments, including production patching, upgrades, and troubleshooting
• Experience managing virtual machine infrastructure, including provisioning, resource management, and lifecycle operations across on-premises and/or cloud platforms
• Experience with a modern monitoring and observability platform; Datadog preferred, with equivalent experience in SolarWinds, Grafana, AppDynamics, New Relic, or similar platforms considered
• Proficiency in at least one scripting language such as PowerShell, Python, or Bash
• Experience operating hybrid infrastructure across colocation or on-premises data centers and public cloud environments
• Experience with patch management tooling such as Ansible, PatchMyPC, SCCM, or WSUS in a production environment
• Strong troubleshooting and problem-solving skills across infrastructure, operating systems, and cloud environments
• Experience with Azure and Google Cloud Platform (GCP)
• Familiarity with Infrastructure as Code tools such as Terraform or ARM templates
• Experience with Ansible for configuration management and patching automation
• Familiarity with SRE concepts, including SLIs, SLOs, error budgets, toil reduction, and reliability engineering practices
• Exposure to VMware vSphere, ESXi, and vCenter administration
• Exposure to GitLab CI/CD or similar pipelines for infrastructure automation workflows
• Experience with monitoring and observability technologies such as Datadog, OpenTelemetry, Signoz, or equivalent platforms
• Strong written and verbal communication skills, with the ability to create clear technical documentation and operational runbooks
• Relevant certifications such as AZ-104 (Azure Administrator), Google Cloud Associate, VMware VCP, or Ansible equivalent are a plus