Remote Ai Infrastructure Engineer Jobs in Chicago, IL

Harvest is seeking a highly seasoned Hybrid Infrastructure Engineer III to join our team in a full-time capacity as a senior technical resource responsible for the engineering, administration, and operational excellence of our hybrid infrastructure environment. This role supports a production environment built on VMware and a disaster recovery environment being consolidated from on-premises and AWS into Microsoft Azure.

The Hybrid Infrastructure Engineer III will serve as a subject matter expert across both the VMware and Azure platforms, ensuring stability, security, and performance throughout the infrastructure stack. This individual will play a key role in decommissioning legacy DR sites (on-premises and AWS-based), supporting the build-out and steady-state management of Azure-based DR services, and maintaining the reliability of VMware-based production systems.

This is a hands-on, senior-level technical role focused on execution and operational leadership. The individual will work closely with the Systems Engineering Manager, internal teams, and external partners to maintain infrastructure, drive continuous improvement, and uphold organizational standards across the hybrid environment.

VMware Production Environment

• Administer and support VMware environments (vSphere 8.x and 9.x), including VM provisioning, lifecycle management, and performance tuning
• Manage and maintain VMware vSAN storage infrastructure and associated datastores
• Administer TrueNAS storage systems providing NFS datastores to VMware clusters
• Support object storage platforms such as MinIO (S3-compatible storage)
• Monitor VMware environment health and performance using vRealize Operations (vROps) and VMware Log Insight
• Perform routine system maintenance, patching, and upgrades across all VMware infrastructure components
• Troubleshoot infrastructure issues across compute, storage, network, and virtualization layers

Azure Disaster Recovery Environment

• Support the migration and consolidation of disaster recovery services from on-premises and AWS environments into Microsoft Azure
• Administer and maintain Azure cloud environments, including compute, storage, and networking resources for DR operations
• Develop, document, and enforce cloud standards, including naming conventions, tagging, and resource management
• Implement monitoring and alerting systems within Azure to ensure DR readiness and system reliability
• Monitor and report on Azure usage and costs; identify and implement cost optimization opportunities
• Support the decommissioning of legacy DR infrastructure, including VMware on AWS and on-premises DR sites

Windows Server and Identity Services

• Manage Windows Server environments (2019 and newer), including:
  • Active Directory (Domain Services, Group Policy)
  • DNS, DHCP
  • File and Print Services
  • Certificate Services (PKI)
  • Remote Desktop Services (RDS)
• Support Windows 11 endpoint environments in a virtualized or enterprise setting

Networking

• Maintain and troubleshoot networking infrastructure including pfSense firewalls and OpenVPN remote access solutions
• Manage VLANs, routing, switching, and TCP/IP networking across the hybrid environment
• Ensure connectivity and network reliability between production (VMware) and DR (Azure) environments

Security and Compliance

• Implement and maintain security controls across both VMware and Azure platforms, including identity and access management
• Maintain access control policies and procedures across the hybrid environment
• Support compliance requirements and audit readiness through monitoring of system logs and audit trails
• Ensure consistent application of governance practices across on-premises and cloud infrastructure

Backup, Recovery, and Business Continuity

• Manage backup, recovery, and business continuity processes across the hybrid environment
• Support and monitor replication using NAKIVO for VMware-based backup and disaster recovery
• Validate DR readiness and participate in DR testing and failover exercises

Vendor Coordination

• Serve as a key internal technical contact for external cloud consultants and service providers
• Track vendor deliverables and ensure alignment with project expectations
• Facilitate knowledge transfer from external partners to internal teams

Documentation and Process Improvement

• Create and Maintain comprehensive documentation for all infrastructure configurations, processes, and standards
• Develop and improve operational procedures for hybrid infrastructure management
• Identify opportunities for automation and efficiency improvements across the environment

Required Education and Experience

• Bachelor's degree in Computer Science, Information Technology, Information Systems, Cybersecurity, or a related field; or an Associate's degree with 7 or more years of experience in information technology
• Minimum 7 years of progressive experience in systems engineering, infrastructure operations, or cloud engineering roles
• Minimum 5 years of hands-on experience with VMware (vSphere, vSAN, replication)
• Minimum 3 years of hands-on experience with Microsoft Azure
• Deep knowledge of Windows Server (2019+) and Active Directory

Technical Knowledge and Skills

• Strong hands-on experience across VMware and Azure platforms in a hybrid operating model
• Experience with Infrastructure as Code tools (e.g., Terraform)
• Experience leading or supporting cloud migration and DR consolidation projects
• Strong understanding of core infrastructure services: DNS, DHCP, TCP/IP networking, Group Policy, identity and access management
• Experience with storage technologies: NAS/SAN (TrueNAS or similar), NFS datastores, object storage (S3-compatible systems such as MinIO)
• Experience with monitoring and alerting tools (PRTG, vROps, Azure Monitor, or similar)
• Familiarity with firewall and VPN technologies (pfSense, OpenVPN, or equivalents)
• Scripting and automation experience (PowerShell preferred; familiarity with Bash/Python a plus)
• Strong troubleshooting skills across compute, storage, network, and virtualization layers
• Experience working in regulated environments

Security and Compliance Knowledge

• Knowledge of security best practices across both on-premises and cloud environments, including identity and access management
• Familiarity with logging, monitoring, and audit processes
• Understanding of regulatory or compliance frameworks preferred

Preferred Certifications

• VMware Certified Professional (VCP)
• Microsoft Azure certification (e.g., Azure Solutions Architect, Azure Administrator)
• Microsoft certifications (AZ-800, or equivalent)
• Networking certifications (Network+, or equivalent)

• Prolonged periods of sitting at a desk and working on a computer
• Ability to operate computer equipment
• Ability to occasionally walk, stand, bend, or reach when accessing equipment, cabling, or hardware components
• Ability to communicate effectively in person and via electronic means

• Travel to our Production Data Center in a near northwest suburb of Chicago as needed.

This description is not designed to cover or contain a comprehensive listing of activities, duties, or responsibilities that are required of the employee for this job. Primary duties, assisting duties, and other department responsibilities and activities may change at any time without notice.

Remote Work Environment Requirements: 

• Dedicated, quiet workspace free from distractions to maintain focus and accuracy.
• Reliable high-speed internet connection to support secure document processing and collaboration.
• Ability to meet deadlines in a remote setting while maintaining attention to detail.
• Strong self-discipline and time management skills to work independently and efficiently.
• Comfortable using remote communication tools (e.g. email, Microsoft Teams, Zoom) for team collaboration.

Benefits:

This is a full-time position with competitive compensation and good work/life balance.

• Health insurance
• Paid Time Off
• Disability insurance
• Paid holidays
• 401k with employer contribution
• Remote work environment
• Generally, promotion within firm

Harvest Valuations LLC is an equal opportunity employer and does not discriminate based upon race, color, religion, sex, sexual orientation, pregnancy, marital status, national origin, citizenship, veteran status, ancestry, age (over 40), physical or mental disability, medical condition (cancer-related), gender identity or expression, genetic information including sickle cell or hemoglobin C trait, or any other consideration made unlawful by applicable federal, state, or local law.

We are not seeking agency assistance with this role.

We are unable to consider candidates who require current or future visa sponsorship for employment in the United States. Candidates must be authorized to work in the US without current or future visa sponsorship or transfer.