Systems Administrator (Windows, Azure, Networking)

About Delavan Holdings

Delavan Holdings is a diversified holding company with interests spanning automotive retail, RV dealerships, hospitality, logistics, industrial services, and professional services across Wisconsin and the greater Midwest. Our portfolio includes Kunes Auto Group, Kunes RV, Lake Lawn Resort, Camp Timber-Lee, G10 Fulfillment, and Ignition Dealer Services. The Office of the CTO is building a small, senior technology team at the holding company that serves every operating company in the portfolio, and this is one of five roles we are adding to it.

This is the hands-on systems and network administration role at the holding company. You will keep core IT systems patched, monitored, backed up, and genuinely recoverable, serve as the escalation point past frontline support, and drive consistency across entities that have historically each done things their own way.

What You'll Do

• Administer on-premises Active Directory across entities, including domains, group policy, DNS, and DHCP, and maintain hybrid identity sync into Entra ID in partnership with the Platform Engineer
• Manage the full user lifecycle with standardized provisioning, deprovisioning, and group and access management
• Administer the workplace productivity and collaboration suite across entities, whether Microsoft 365 or Google Workspace, including email, file sharing, and licensing
• Manage endpoints through their lifecycle in Intune or similar tooling: enrollment, configuration baselines, patching, and secure disposal
• Build, operate, and maintain Windows and Linux servers and the virtualization platforms beneath them, such as Hyper-V or VMware, both on-premises and in Azure
• Administer site networking at the parent company and operating-company locations, including switching, VLANs, firewalls, wireless, and VPN connectivity, with configurations documented and consistent across sites
• Own backup and recovery for systems in scope, including schedules, monitoring, and regular restore testing
• Own the certificate, DNS, and domain lifecycle across entities, including public DNS records, domain registrations and renewals, and TLS certificate issuance and expiry, so nothing lapses silently
• Maintain IT asset and license management across entities, including hardware and software inventory, license assignments and true-ups, and renewals
• Monitor system health, respond to alerts, and act as the escalation point beyond frontline support: troubleshoot to root cause, communicate status, and document RCAs for significant incidents
• Implement a standardized ticketing platform and escalation process across operating companies, in partnership with operating-company IT teams
• Standardize and automate routine administration with PowerShell, so common tasks are repeatable, documented, and auditable
• Follow a disciplined change process in which changes are requested, approved, tested, applied, and logged
• Maintain SOPs, runbooks, version-controlled scripts in GitHub, network maps, and system diagrams so others can support the environment
• Partner with Engineering, IT, vendors, and internal stakeholders to support acquisitions, site turn-ups, and office moves

 What We're Looking For

• 3 or more years in systems administration or a closely related role operating production IT systems across cloud and on-premises environments
• Hands-on Active Directory administration, including group policy, DNS, and DHCP, plus hybrid identity into Entra ID
• Experience administering Microsoft 365 or Google Workspace, including email, collaboration, and file-sharing administration. Comfort with the shared concepts matters more than which platform
• Endpoint management tooling such as Intune, including configuration baselines and patch management
• Experience with RMM, SIEM, and endpoint monitoring tools for visibility, alerting, and remote administration across distributed sites
• Experience building and maintaining Windows and Linux servers and virtualization platforms such as Hyper-V or VMware
• Experience managing Azure infrastructure, including virtual machines, storage, and supporting networking
• Hands-on site networking: switching, VLANs, firewalls, wireless, and VPNs
• Strong PowerShell scripting for automation and administration, with documentation and repeatability as habits
• Backup and recovery practice, including restore testing
• Sound security and data governance habits, including least-privilege access and careful handling of sensitive data across multiple entities
• Strong written and verbal communication, with clear documentation habits and comfort working with non-technical stakeholders
• Familiarity with AI tools in daily work, such as drafting documentation and troubleshooting, paired with the judgment to verify what they produce
• Willingness to travel periodically to operating-company sites

What Sets You Apart

• Relevant certifications such as Microsoft, CompTIA, or virtualization credentials
• You have supported acquisitions, site turn-ups, or office moves and know how much of that work is logistics rather than technology
• You have worked under financial-reporting controls or audit requirements such as change logging and access review
• You fix causes rather than tickets, and you can point to a recurring issue you permanently eliminated
• You write the documentation you wish someone had handed you
• Background in automotive retail, hospitality, logistics, or multi-entity or holding company environments

Why Delavan Holdings

• A small, senior team where you own real surface area instead of a slice of someone else's system
• Greenfield work: much of what you build will be the first version of itself at this company
• A portfolio spanning automotive retail, RV, hospitality, logistics, and fulfillment, which means genuinely varied technical problems
• AI is not a side project here. It is budgeted, used daily by leadership, and expected to be part of how engineering work gets done
• Direct access to the CTO and to the operators you are building for, with a short path from idea to production
• Based in the Lake Geneva region of southeastern Wisconsin, with an entrepreneurial, low-bureaucracy culture

Delavan Holdings is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.