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Workbox · 23 hours ago

Director of Information Technology

Chicago, IL

Full-time

Onsite

Director/Executive

$100K/yr - $160K/yr

10+ years exp

Workbox is a national workspace operator that goes beyond coworking, helping businesses thrive through a variety of workspace solutions. The Director of Information Technology will lead and scale technology operations across multiple locations, overseeing IT strategy, infrastructure, service delivery, security, and vendor management.

CoworkingIncubatorsReal Estate

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

Qualification

IT strategyMicrosoft cloud technologiesVendor managementIT process developmentMulti-site supportTeam developmentInterpersonal skillsProblem-solvingTime managementCollaborationAdaptability