About the Role

Join Robert Half's dynamic AI & Technology Solutions team as an IT Manager/Director in the heart of Chicago, Illinois. Reporting directly to the Head of AI & Technology Solutions, you'll be the linchpin in transforming our internal IT operations into a seamless, secure, and user-centric powerhouse. This pivotal role partners closely with Product and Data leadership to align cutting-edge IT infrastructure with groundbreaking AI initiatives and future workflows.

We're seeking a strategic IT leader who thrives in a hybrid environment, committing to at least three days per week in our state-of-the-art Chicago office. Your mission: elevate the technology experience, fortify cybersecurity defenses in tandem with our outsourced vCISO, and manage our trusted MSP to deliver white-glove support. If you excel at vendor orchestration, hands-on troubleshooting, and driving operational excellence, this Chicago IT Manager/Director position at Robert Half offers the platform to make a lasting impact.

With a competitive salary starting at $120,000, this full-time role is perfect for seasoned IT professionals passionate about cybersecurity, cloud platforms, and AI-enabled innovation. Keywords: IT Manager Chicago, Director of IT Illinois, MSP management jobs, cybersecurity leadership roles, Google Workspace admin careers.

Key Responsibilities

Elevate Internal Technology Experience

• Significantly improve internal satisfaction with technology and tech support across the organization.
• Ensure team members feel supported, empowered, and unencumbered by avoidable technical issues through proactive measures.
• Collect and act on ongoing feedback to continuously refine and optimize the user experience.

Manage Managed Service Provider (MSP)

• Oversee the firm’s MSP relationship, ensuring SLAs are consistently met or exceeded with rigorous oversight.
• Drive a high-touch, white-glove support culture that prioritizes user needs.
• Own all vendor contracts and renewals for hardware, software, cybersecurity, and IT services.
• Hold MSP and security partners accountable via structured performance reviews and metrics.
• Lead quarterly MSP and vCISO alignment sessions to synchronize strategies.
• Step in hands-on when needed to expedite resolutions or validate MSP deliverables.

Own IT Infrastructure

• Manage end-to-end hardware lifecycle planning, procurement, inventory tracking, and asset management.
• Coordinate seamless onboarding and offboarding processes in partnership with HR and external partners.
• Administer core platforms like Google Workspace, Slack, Box, Microsoft 365, and other SaaS applications.
• Ensure robust identity and access management through Okta implementation and maintenance.
• Oversee JAMF or Intune policies with MSP support for device management.
• Maintain accurate internal documentation, runbooks, and system records for operational continuity.
• Handle escalated troubleshooting to minimize downtime and frustration.

Cybersecurity Leadership

• Serve as the primary internal point of contact for all information security matters.
• Conduct basic internal checks including device compliance, MFA enforcement, and endpoint security protocols.
• Partner strategically with vCISO providers on threat monitoring, SIEM/log reviews, risk assessments, vulnerability scanning, and incident response planning.
• Support the evaluation and selection of top-tier vCISO partners to bolster defenses.
• Ensure crystal-clear alignment and execution of security responsibilities across all vendors and teams.

Required Qualifications

To succeed in this IT Manager/Director role at Robert Half in Chicago, IL, you bring:

• 5+ years of progressive IT management or senior operational experience in dynamic environments.
• Proven track record managing MSPs, vCISOs, and multi-vendor ecosystems with SLA enforcement.
• Expert-level proficiency in Google Workspace, Microsoft 365, Slack, Box, Okta, JAMF/Intune.
• Strong cybersecurity acumen, including threat monitoring, compliance checks, and incident response.
• Hands-on expertise in hardware lifecycle, procurement, IAM, and escalated support.
• Exceptional vendor management, contract negotiation, and performance accountability skills.
• Experience aligning IT with AI/ML initiatives and cross-functional teams (Product/Data).
• Hybrid work adaptability with in-office presence (3+ days/week in Chicago).
• Bachelor's in IT, Computer Science, or equivalent; certifications like CISSP, CISM a plus.
• Superior communication and stakeholder management for leadership reporting.

Why Join Us

At Robert Half, you'll pioneer a modern, reliable, secure tech environment that fuels AI innovation and seamless collaboration. Enjoy a hybrid model in vibrant Chicago, competitive $120K+ salary, comprehensive benefits including 401(k) match, PTO, health coverage, and professional growth opportunities. Be part of an elite AI & Technology Solutions team driving world-class user experiences. Apply now for this Chicago IT leadership role and shape the future of tech at Robert Half!