Senior Manager of Systems Administration

About the role

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.

Responsibilities

• Architect and execute strategy across hybrid infrastructure, endpoint engineering, identity and access management, mobility platforms, and restaurant technology.
• Drive automation, orchestration, and standardization to reduce manual effort, increase consistency, and improve system reliability.
• 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.
• 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.
• 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.

Requirements

• 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.

Qualifications

• 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.

Skills

• Systems and cloud infrastructure architecture and management.
• Endpoint engineering and management.
• Identity and access management.
• Mobile device management and endpoint security.
• Backup and disaster recovery strategies.
• Monitoring and observability tools.
• Collaboration and teamwork.
• Change management and release management.
• Root cause analysis and incident response.
• Vendor management and relationship building.
• Technical leadership and coaching.

Benefits

• 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).