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Senior Manager of Systems Administration

Cooper's Hawk Winery & Restaurants

Downers Grove, IL

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JOB DETAILS
JOB TYPE
Full-time
SKILLS
Accidental Death and Dismemberment (AD&D), Android, Asset Management, Automation, Benchmarking, Change Management, Cloud Computing, Coaching, CompTIA Security+, Computer Security, Computer Services, Computer Systems, Continuous Improvement, Customer Experience, DHCP (Dynamic Host Configuration Protocol), DNS (Domain Name System), Data Recovery, Dental Insurance, Disaster Recovery, Documentation, Encryption Software, Endpoint Security, Enterprise Endpoint, File and Print Sharing, High Availability, ITIL (IT Infrastructure Library), Identity Data Management, Incident Management, Insurance, Inventory Management, Leadership, Logistics, Mac Operating System, Maintain Compliance, Manufacturing Data Management, Menu Development, Microsoft Active Directory, Microsoft Hyper-V, Microsoft Infrastructure, Microsoft Windows Azure, Microsoft Windows Operating System, Microsoft Windows Server, National Reconnaissance Office (NRO), Network Configuration Management, On Site Support, Operating Systems, Oracle, Oracle Applications, PCI, Prescription Drugs, Printers, Public Key Infrastructure (PKI), Purchasing/Procurement, Release Management/Engineering, Reliability Engineering, Replication and Remote Mirroring, Request for Proposals (RFP), Restaurant, Retail, Root Cause Analysis, Software Engineering, Software Patches, Source Code/Configuration Management (SCM), Supplier Relationship Management (SRM), System Center Configuration Manager (SCCM), System Lifecycle, Systems Administration/Management, Systems Reliability, Team Lead/Manager, Team Player, Technical Leadership, Telemedicine, Telemetry, VMWare, Vendor/Supplier Licensing, Vendor/Supplier Relations, Virtual Machine (VM), Virtualization, Vision Plan, Win32 API (Application Programming Interface), Windows PowerShell, iOS
LOCATION
Downers Grove, IL
POSTED
18 days ago

Ready to be part of something extraordinary? At Cooper’s Hawk, connection is at the heart of everything we do, and we’re looking for passionate people to join us. When you become part of our team, you step into a collaborative, supportive culture built on Uncompromising Hospitality, where standards and genuine care come together to create something truly unforgettable.  As we continue our exciting journey, you’ll help us deliver unforgettable experiences to our Wine Club Members and the entire Cooper’s Hawk community. Join us, and let’s turn moments into lasting memories.
 
The Senior Manager of Systems Administration at Cooper’s Hawk is a hands-on technical leader who directs a high performing team of system administrators, engineers and endpoint specialists who are responsible for reliability, performance, security, and lifecycle of all compute environments—restaurant systems, cloud platforms, corporate servers, end‑user devices, and mobility technologies. This role ensures that mission‑critical hospitality systems remain stable, scalable, and secure across 70+ locations and the Restaurant Support Center.
 
You will architect and execute strategy across hybrid infrastructure, endpoint engineering, identity and access management, mobility platforms, and restaurant technology. A major focus of this role is driving automation, orchestration, and standardization to reduce manual effort, increase consistency, and improve system reliability. Flexibility is required to support a national, seven‑day‑a‑week operation.
 
How You Will Succeed:
 
Systems & Cloud Infrastructure
  • Architect, manage, and optimize hybrid compute environments spanning Azure, onprem Windows Server, and restaurant back‑office systems.
  • Oversee core infrastructure services including Active Directory, Azure AD, Group Policy, DNS/DHCP, PKI, file/print services, virtual machine maintenance, and identity governance.
  • Ensure patching compliance and OS lifecycle management using Intune, SCCM/MECM, Azure Update Manager, Automox and automation pipelines.
  • Manage backup and disaster recovery strategies using Azure Backup, Arserve, site‑to‑site replication, and retention policies.
  • Implement and maintain monitoring and observability.
  • Partner with Field Services/NRO partners to standardize and deploy restaurant back‑office servers, network appliances, and local computer resources.
  • Collaborate with Security on vulnerability remediation, system hardening baselines, CIS benchmarks, and secure configuration standards.
 
Restaurant & Hospitality Technology
  • Partner with internal teams to assist with uptime, performance, and lifecycle of restaurant systems including Oracle Simphony POS, KDS, BOH servers, payment terminals, printers, and local infrastructure.
  • Maintain configuration standards, patching, and version control for POS and KDS environments.
  • Support NRO (new restaurant opening) technology builds including server imaging, POS provisioning, network configuration, and vendor coordination.
  • Implement remote management and telemetry solutions for proactive issue detection and automated remediation.
  • Ensure PCI‑aligned system hardening, endpoint protection, and secure connectivity across all restaurant locations.
 
End User Compute (EUC) & Mobility Management
  • Lead enterprise endpoint engineering across Windows, macOS, iOS, and Android platforms.
  • Administer and evolve Intune, JAMF, and other MDM/EMM platforms for device compliance, conditional access, encryption, and application deployment.
  • Standardize imaging and provisioning using Autopilot, ADE/DEP, JAMF enrollment workflows, and automated configuration scripts.
  • Oversee software packaging, versioning, and deployment pipelines using Win32 apps, MSI packaging, PowerShell DSC, and configuration baselines.
  • Manage the full EUC lifecycle including procurement, asset tagging, inventory management, repair logistics, and secure disposal.
 
Support, Reliability & Operational Readiness
  • Implement change management, release management, and maintenance windows aligned with ITIL practices.
  • Ensure high‑availability coverage for critical systems during business hours, holidays, and peak restaurant operations.
  • Drive root‑cause analysis (RCA) and post‑incident reviews with a focus on automation and prevention.
 
Team & Vendor Leadership
  • Foster a culture of “automate first” thinking, continuous improvement, and cross‑functional collaboration.
  • Lead a team of system administrators, cloud engineers, and EUC specialists focused on uptime, automation, and service excellence.
  • Build technical depth through coaching, training, and cross‑functional collaboration.
  • Manage vendor relationships, licensing, hardware procurement, and RFP processes for mobility, compute, and managed services.
  • Partner with restaurant leadership, service desk, security, networking, and application teams to deliver seamless technology experiences.
 
What You’ll Need:
 
Required
  • 8+ years in systems or infrastructure engineering roles, including 3+ years in technical leadership or management.
  • 5+ years of hands‑on experience with Microsoft infrastructure: Windows Server, Active Directory, Azure AD, M365, Intune/SCCM/MECM.
  • Strong background supporting distributed, multi‑unit brick‑and‑mortar environments (restaurant or retail preferred).
  • Expertise with MDM/EMM platforms, endpoint security, compliance policies, and device lifecycle management.
  • Experience with cloud infrastructure, virtualization (Hyper‑V/VMware), backup solutions, monitoring tools, and system hardening.
 
Preferred
  • Familiarity with Oracle Simphony POS, KDS, and restaurant back‑office systems.
  • Familiarity with ITIL frameworks, asset lifecycle management, and compliance reporting.
  • Experience supporting new restaurant openings and field operations.
  • Certifications such as AZ‑104, AZ‑305, MDM/EMM certifications, ITIL Foundation, Security+, etc.
  • Multi‑unit retail + restaurant experience is a strong plus.
 
What You Bring to Cooper’s Hawk
  • A passion for building reliable, secure, and service‑driven technology that enhances the guest and team member experience.
  • A collaborative mindset with the ability to partner across engineering, operations, and field teams.
  • A process‑oriented approach with strong execution, documentation, and continuous improvement.
  • A commitment to technical excellence, team leadership, and hospitality‑focused innovation.
  • A belief that anything done three times should be automated.
 
Compensation Range: $120,000-$150,000 + bonus potential. The final offered salary will be based on several factors, including but not limited to the candidate’s depth of experience, skill set, qualifications, and internal pay equity.
 
What You’ll Get:   
  • Incredible Discounts:
    • Monthly Dining Allowance
    • 50% Dining and Carryout
    • 40% Retail Wine
    • 20% Retail and Private Events
    • Monthly Complimentary Wine Tasting for Two 
  • Medical, Prescription, Dental, Vision Insurance plus Telemedicine and Wellness Program
  • Company Matching 401(k) Retirement Savings Plan
  • Flexible Savings Accounts- Health and Dependent Care
  • Health Savings Account 
  • Long-Term Disability; Voluntary Short-Term Disability
  • Basic Life and AD&D Insurance (with option to purchase additional coverage)
  • Paid Parental Leave
  • Highly Competitive Pay plus Team Member Incentives & Rewards  
  • Paid Time Off 
  • Milestones Recognition Program
  • Complimentary Gym Membership in RSC Building
  • Hybrid Work Week (3 days in office, 2 days remote, depending on role)
 
Cooper’s Hawk is an equal opportunity employer.  All qualified applicants are considered for employment without regard to the person’s race, color, religion, national origin, sex, sexual orientation, age, marital status, veteran status, disability, or any other characteristic protected by applicable law. Cooper’s Hawk makes reasonable accommodations during all aspects of the employment process, including during the interview process.  
 
The information provided above indicates the general nature and level of work required of the position and is not a comprehensive list of all responsibilities or qualifications. The Benefits list is only a highlight of some of the benefits offered to team members; eligibility for certain benefits apply.  

About Us

Cooper's Hawk features a Napa-style tasting room with wine-inspired retail for entertaining and a full-service restaurant, bar and private event space, offering a modern-yet-casual dining experience. Each scratch-kitchen menu item is designed to pair with our wines. Speaking of wine...the Cooper's Hawk Wine Club is perhaps the largest in the world, offering not only top-notch award-winning wines but also exclusive Wine Club membership benefits, including curated dining and travel experiences. Since 2005, we've brought the Napa Valley experience to our guests and Wine Club members, and now, with Piccolo Buco by Cooper’s Hawk, we’re bringing the vibrant flavors of Rome to them as well. Together, we’re creating a lifestyle brand like no other.

About the Company

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Cooper's Hawk Winery & Restaurants

After four years of planning and construction, Cooper’s Hawk Winery & Restaurant opened in 2005 in Orland Park, a south suburb of Chicago. The concept was unique. We would create a signature menu with a selection of dishes designed to pair perfectly with our own Cooper’s Hawk wines, made in our own private winery. With sophisticated food and exceptional wines, our concept was born.

The Cooper’s Hawk concept includes four distinct components: an upscale casual dining restaurant, full-service bar, private barrel-aging room, and Napa-style tasting room and retail gift store…all under one roof. Each Cooper’s Hawk location is distinctive in layout and décor, but carries the same warmth and elegance that guests have come to expect.
INDUSTRY
Restaurant/Food Services
FOUNDED
2005
WEBSITE
https://www.coopershawkwinery.com/