IT Manager – Hands-On Technology Leader

McCready Law; Chicago (IL); On-site; USD 100,000 - 120,000; Full time

Benefits offered by this job

Medical insurance

Dental insurance

Vision insurance

Retirement benefits

Paid time off

Paid holidays

Job summary

McCready Law in Chicago, IL is seeking an experienced IT Manager to lead our technology operations, supervise two full-time IT staff, and ensure reliable, secure tech support across our Beverly and downtown Chicago offices.

You will hands-on troubleshoot Microsoft 365, manage external IT vendors, handle onboarding/offboarding, access control, backups, and ongoing system improvements while maintaining documentation and a proactive, customer-focused approach.

Qualifications

• At least five years of IT support, systems administration, or technology operations experience.
• At least two years of supervising IT staff or leading technical teams.
• Hands-on troubleshooting with Microsoft 365, devices, connectivity, and IAM.
• Familiarity with Entra ID / Active Directory, MFA, endpoint management, networking, and cybersecurity basics.
• Experience working with managed service providers or external vendors.
• Proven ability to lead, set priorities, and hold teams accountable.
• Ability to juggle priorities and keep tickets moving with a focus on customer service.
• Experience in law firm or professional services IT is a plus; multiple offices and remote teams preferred.

Responsibilities

• Lead and manage two IT employees, including assigning work, coaching, developing skills, evaluating performance, and ensuring accountability.
• Oversee daily IT operations and provide timely, reliable technical support.
• Personally troubleshoot escalated issues involving computers, Microsoft 365, printers, networks, phones, and conferencing equipment.
• Provide on-site support at Beverly and downtown Chicago offices.
• Manage outside IT service providers and vendors to ensure timely issue resolution.
• Oversee onboarding and equipment readiness for new hires; coordinate account access and deactivation for departures.
• Assist with access control, MFA, endpoint protection, cybersecurity practices, backups, and system reliability.
• Maintain IT inventory, software licenses, and documentation.
• Lead technology projects, upgrades, and new solutions to improve productivity.
• Identify recurring problems and implement preventive solutions.
• Manage IT budgets, vendor performance, and service expectations while reporting to leadership.

Skills

Microsoft 365

Team leadership

Customer service mindset

Communication

Identity & access management

Education

Technology-related degree

Tools

Entra ID / Active Directory

MFA

Endpoint management

Job description

Description

Chicago, IL | On-Site | Full-Time

Salary: $100,000–$120,000 annually

Can You Lead an IT Team AND Fix the Problem?

Are you the person everyone calls when technology stops cooperating? Do you enjoy solving a good technical mystery, keeping systems running smoothly, and making sure the printer doesn't win?

If you can lead an IT team, troubleshoot a Microsoft 365 issue, and still have the patience to explain why someone's second monitor isn't working, we'd like to meet you!

McCready Law, a growing personal injury law firm, is looking for an experienced, hands-on IT Manager to lead our technology operations, supervise two full-time IT employees, and keep our team connected, supported, and productive.

And when we say hands-on, we mean it.

This isn't a position where you'll simply oversee employees, forward support tickets, and attend strategy meetings. We're looking for someone who genuinely enjoys technology, gets into the weeds, solves problems, supports employees, and takes ownership of the results.

What You'll Be Doing

• Lead and manage two full-time IT employees, including assigning work, coaching, developing their skills, evaluating performance, and ensuring accountability.
• Oversee daily IT operations and ensure employees receive timely, reliable technical support.
• Personally troubleshoot escalated technology issues involving computers, Microsoft 365, printers, networks, phones, conference room equipment, and connectivity.
• Provide regular on-site technical support at our Beverly and downtown Chicago offices.
• Manage our outside IT service provider and other technology vendors, ensuring issues are resolved rather than endlessly passed around.
• Oversee technology setup for new hires, including equipment, accounts, secure access, and readiness for their first day.
• Coordinate timely account deactivation and equipment recovery when employees leave the firm.
• Help manage user access, multifactor authentication, endpoint protection, cybersecurity practices, backups, and system reliability.
• Maintain accurate technology inventory, software licenses, equipment assignments, and IT documentation.
• Lead technology projects, equipment upgrades, system improvements, and new solutions that make everyone's work easier.
• Identify recurring IT problems and implement solutions that prevent them from happening again.
• Manage IT budgets, vendor performance, and service expectations while keeping leadership informed.

What We're Looking For

• At least five years of progressively responsible IT support, systems administration, or technology operations experience.
• At least two years of experience supervising IT employees, leading technical teams, or managing significant technology operations.
• Strong hands-on troubleshooting experience with Microsoft 365, employee devices, connectivity, and identity and access management.
• Familiarity with Entra ID or Active Directory, MFA, endpoint management, networking, and cybersecurity fundamentals.
• Experience working with managed service providers or external IT vendors.
• Demonstrated ability to lead employees, assign priorities, provide feedback, and hold team members accountable.
• The ability to manage competing priorities, resolve escalated issues, and keep support tickets moving.
• Strong communication skills and a customer-service mindset.
• Someone who enjoys helping people and can explain technical issues without making everyone feel like they need a computer science degree.
• Law firm or professional services IT experience is preferred, but not required. Experience supporting multiple offices and remote or international teams is also a plus.
• Relevant IT certifications or a technology-related degree are preferred. Equivalent professional experience is welcome.

The Type of IT Manager Who Will Thrive Here

• Enjoys leading and developing employees but hasn't forgotten how to troubleshoot.
• Takes ownership instead of saying, "That's the vendor's problem."
• Knows when to delegate and when to roll up your sleeves.
• Can balance an urgent support ticket with an important long-term project.
• Understands that cybersecurity and reliable systems are serious business.
• Believes good documentation is almost as important as a good fix.
• Can hold employees and vendors accountable while maintaining a positive, supportive work environment.
• Knows that great IT support is about people as much as technology.
• Isn't afraid to get your hands dirty solving a problem.
• In other words, we're looking for someone who can lead the team, manage the technology, and still save the day when something inevitably decides to stop working five minutes before an important meeting.

Why McCready Law?

• You'll have the opportunity to make a visible difference in how our firm operates.
• You'll lead a small internal IT team, work with outside technology partners, improve processes, strengthen our technology support, and help shape the future of our IT operations.
• We're looking for someone who brings ideas, takes initiative, develops their employees, and enjoys building a reliable technology environment—not just maintaining the status quo.

Position Details

• Full-time, on-site position supporting both our Beverly and 200 W. Madison offices in Chicago.
• Monday through Friday, 8:30 a.m. to 5:00 p.m.
• Reports directly to the Chief Operating Officer.
• Directly supervises two full-time IT employees.
• Occasional after-hours support may be required for urgent technical issues.
• Annual salary: $100,000–$120,000, depending on qualifications and experience.
• Benefits include medical, dental, vision, retirement benefits, paid time off, paid holidays, and other eligible firm-sponsored benefits.

McCready Law is an Equal Opportunity Employer. We make employment decisions without regard to any legally protected characteristic and provide reasonable accommodations in accordance with applicable law.