The IT Operations Manager is responsible for the reliability, scalability, and evolution of the company’s IT environment. This role is accountable not just for keeping systems running, but for continuously improving how IT operates as the business grows and complexity increases.

This is a hands-on leadership role for someone who enjoys running stable operations and is motivated to modernize them—reducing friction, increasing automation, and scaling capabilities without adding unnecessary complexity or risk. The IT Operations Manager reports directly to the Director of IT and plays a key role in turning strategy into durable operational outcomes.

Operating Philosophy

We believe strong IT operations are defined by two things: stability today and improvement tomorrow. Firefighting is sometimes unavoidable—but recurring issues, manual workarounds, and fragile systems are signals to fix the root cause. This role is expected to reduce noise over time, not normalize it.

This role requires a true IT generalist—someone comfortable operating across endpoints, identity, networks, SaaS platforms, vendors, and field technology. You don’t need to be the deepest expert in every system, but you must understand how they fit together, where they break, and how to improve them pragmatically.

Key Responsibilities

Operations & Service Delivery

Identify opportunities to improve processes, tooling, and workflows; drive changes that reduce friction, manual effort, and recurring issues
Own daily IT operations across corporate offices, field locations, and remote users
Ensure availability and performance of core systems including networks, endpoints, collaboration tools, and SaaS platforms
Oversee incident, problem, and change management processes; act as escalation point for complex issues
Monitor SLAs, KPIs, and service health; drive continuous improvement and root-cause remediation

Infrastructure & Systems

Administer and support identity, endpoint, and device management platforms (e.g., MDM, IAM, EDR)
Maintain and improve network connectivity across HQ and field sites, including ISP coordination and failover readiness
Support cloud and SaaS platforms (Microsoft 365, collaboration, security tooling) with a focus on reliability and cost efficiency
Partner with security stakeholders to enforce baseline controls, patching, and compliance requirements

Vendor & Partner Management

Manage relationships with MSPs, network providers, hardware vendors, and software partners
Coordinate onboarding/offboarding of vendors; review contracts, renewals, and performance
Ensure vendors meet security, compliance, and service expectations

Team Leadership & Enablement

Lead and mentor support resources (internal and/or contracted), setting priorities and standards
Establish clear runbooks, documentation, and operating procedures
Provide hands-on support when needed; lead by example

Projects & Continuous Improvement

Execute IT initiatives and improvements aligned to the IT roadmap (automation, tooling upgrades, standardization)
Support rollouts for new locations, systems, or devices
Identify opportunities to reduce toil, improve reliability, and enhance end-user experience

Required Skills & Experience

7+ years of progressive IT experience in operations, infrastructure, service delivery roles, and innovation
Proven experience owning day-to-day IT operations in a multi-site, distributed, or retail environment
Strong operational mindset with the ability to manage across multiple technical domains using standards, documentation, and repeatable processes
Experience administering and supporting modern endpoint, identity, and collaboration platforms
Working knowledge of ITIL-based incident, problem, and change management practices
Demonstrated success managing MSPs, carriers, and technology vendors
Strong troubleshooting skills with the ability to act as an escalation point
Excellent written and verbal communication skills

Preferred Experience With Systems & Platforms
Experience with modern, enterprise-grade platforms in the following areas is preferred:

Identity & Access Management: Cloud-based identity directories and SSO platforms
Endpoint & Device Management: Windows, macOS, and mobile device management (MDM)
Collaboration & Productivity: Email, chat, video conferencing, and document collaboration suites
Networking & Connectivity: Firewalls, wireless, SD-WAN, and multi-site ISP management
Field / Retail Technology: POS systems, kiosks, and distributed edge devices
IT Service Management: Ticketing, asset management, and service monitoring tools
Security & Compliance: Operational security controls, patching, and compliance-aligned practices

Direct experience in multi-location or retail environments is strongly preferred.

Why This Role

This role is ideal for an IT leader who enjoys both operational responsibility and thoughtful improvement—someone who wants to keep systems running and make them better every quarter as the business grows. It offers real ownership, visible impact, and the opportunity to shape how IT operations scale with the business.

About us:

Insomnia Cookies was founded in a college dorm room by then-student, Seth Berkowitz. Fast forward 20 years and so... many....cookies... later, our innovative bakery + delivery concept has become a cult brand known for its rabid following of cookie lovers who crave Insomnia’s warm, delicious delivery all day and late into the night. With an expanding footprint of over 300 stores globally, an experiential, “sweet-easy” concept as the brand’s flagship in Philadelphia, Pa. (where Insomnia Cookies is headquartered), and a rapidly-growing nationwide shipping and gifting portfolio... Insomnia Cookies is revolutionizing the cookie game by truly "Imagining What’s Possible"!

Insomnia Cookies

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