IT Operations Manager

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.

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.

* 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.

* 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.

* 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.

* 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.

* 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.

* 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.

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.

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.

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"!