Director of Information Technology

ABOUT WORKBOX

Workbox is a national workspace operator that goes beyond coworking-our ecosystem accelerates ambition, cultivates connections, and helps businesses thrive . In addition to office space and coworking solutions, we offer connection to a network of investors, professional specialists, and high growth businesses across our entire portfolio. Our workspace products include private offices, reserved desks and floating memberships, as well as meeting rooms and event spaces. We currently operate 13 locations, encompassing over 400,000 square feet, in seven cities across the U.S., and our differentiation has led to us being one of the fastest growing workspace operators in the country.

ABOUT THE OPPORTUNITY

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.

KEY RESPONSIBILITIES

IT Strategy & Leadership 

• 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.

Infrastructure & Systems

• 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.

Service Delivery & Operations

• 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.

Security & Risk Management

• 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.

People & Team Development

• 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.

Collaboration & Enablement

• 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.

Requirements

Required

• 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.

Preferred

• 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.

Benefits

Anticipated salary: $100,000-$160,000 annually (commensurate with experience)

Comprehensive health benefits, including medical, dental and vision coverage

Company-paid life insurance

401(k) plan

Generous paid time off

FSA, HSA and commuter benefits

Ongoing training and professional development