Director of Information Technology

Workbox Holdings, Inc.•Chicago, IL

41d•$100,000 - $160,000•Onsite

About The Position

We are seeking a full-time Director of Information Technology to be based in Chicago at our corporate headquarters. The Director of Information Technology will report directly to the Chief Financial Officer and interact daily with other internal company departments, as well as external vendors, customers, and partners. The Director of Information Technology is a high-impact role responsible for leading and scaling technology operations across a growing, multi-location coworking organization. This position oversees all IT strategy, infrastructure, service delivery, security, and vendor management, while ensuring a seamless technology experience for members and employees alike. The ideal candidate is both strategic and hands on, capable of setting long-term direction while also executing critical initiatives such as new site launches, cloud-first endpoint management, and operational process maturity.

Requirements

10+ years of progressive IT experience, including leadership roles.
Proven experience supporting multi-site or distributed organizations.
Bachelor’s degree in information technology, computer science, or similar field.
Strong background in Microsoft cloud technologies (Microsoft 365, Azure AD, Intune, Autopilot, Power BI).
Experience managing MSPs, vendors, and third-party service providers.
Demonstrated success building IT processes, policies, and operational frameworks.
Ability to balance strategic planning with hands-on execution.
Strong interpersonal skills with the ability to build genuine relationships.
A natural problem-solver who takes initiative and remains adaptable in a growing, dynamic organization.
Highly organized with excellent time management and multitasking abilities.
A team player with a positive attitude and a strong sense of ownership and accountability.

Nice To Haves

Experience in coworking, hospitality, real estate, or multi-location services environments.
Familiarity with HubSpot, Office RND, Zapier.
Experience scaling IT operations during rapid organizational growth.
Familiarity with ITIL best practices and formal change management.

Responsibilities

Owning and executing the companywide IT strategy aligned to business growth, operational efficiency, and security requirements.
Serving as the primary technology partner to executive leadership, translating business objectives into scalable technical solutions.
Developing and maintaining a multi-year IT roadmap to support rapid location expansion.
Establishing and evolving IT governance, policies, and standards across all departments.
Leading end-to-end IT buildouts for new locations, including networking, A/V, identity, endpoints, and collaboration tools.
Owning Microsoft 365, Azure AD, Intune, and Autopilot environments, ensuring secure, cloud-first device provisioning and management.
Overseeing endpoint lifecycle management, including standardization, upgrades, and OS refreshes.
Ensuring reliability, performance, and security across all corporate and member-facing technology.
Designing, implementing, and maintaining core Information Systems to support business operations and member experience.
Driving integration between business platforms (Office RND, NetSuite, HubSpot) to streamline workflows and data consistency.
Leveraging automation tools (e.g., Zapier) to reduce manual processes and improve operational efficiency.
Building and maturing a hybrid support model leveraging MSP partners and internal IT staff.
Owning vendor selection, contract negotiation, SLAs, and ongoing performance management.
Establishing and continuously improving ITIL aligned processes including incident, problem, and change management.
Leading major incident response, escalation, communication, and post-incident reviews.
Partnering with leadership to define and enforce security policies, access controls, and device compliance standards.
Ensuring appropriate identity management, endpoint security, and data protection practices.
Supporting audits, risk assessments, and security initiatives as needed.
Hiring, mentoring, and managing internal IT staff as the organization scales.
Defining roles, responsibilities, and performance expectations for internal and external resources.
Fostering a culture of documentation, accountability, and continuous improvement.
Partnering with cross-functional teams to ensure technology enables business workflows.
Leading the development and adoption of centralized collaboration platforms (e.g., SharePoint).
Ensuring effective communication around technology changes, deployments, and outages.