Your Strategic IT Wingman For Your Chicago Legal practice
Most MSPs focus on tickets and tools. Wingman focuses on outcomes that matter, especially for law firms balancing security, compliance, and client confidentiality.
We help legal teams lead with intent, reduce risk, and modernize IT infrastructure without expanding headcount. From peer-level advisory to tactical execution, Wingman is purpose-built to support firms navigating today’s evolving legal tech landscape.
Accelerate IT and Security with Confidence for your firm
Strategic IT Support for Chicago Law Firms
Wingman is built for law firms with bold goals, lean teams, and limited time to chase specialized talent. Whether you’re preparing for an audit, onboarding a high-stakes client, or facing mounting cybersecurity and compliance demands, Wingman delivers clarity, structure, and senior-level expertise, right when you need it.
This isn’t your typical break-fix support. Wingman acts as a strategic force multiplier for Chicago firms, giving you access to a curated bench of CIOs, CISOs, architects, and engineers. Each one steps in to close specific skill gaps, accelerate outcomes, and move your firm forward.
Designed for modern legal environments, Wingman helps Chicago attorneys and IT leaders bridge the gap between legacy systems and future-ready infrastructure so you can focus on what matters most: serving clients, not putting out fires.
Why Wingman Stands Apart
Most MSPs focus on tickets and tools. Wingman focuses on outcomes that matter to Chicago law firms, strengthening security, closing skill gaps, and keeping your team focused on clients.
We help legal practices lead with intent, prioritize risks, and build a secure, scalable foundation for the future. From peer-level advisory to hands-on execution, Wingman delivers the strategic support your firm needs without adding headcount.
What Wingman Delivers
“Wingman gave us the resources to meet our security objectives without losing momentum on other priorities. Their team brought practical, real-world expertise and acted like a true partner to our internal IT and legal teams.” - , Chief Operating Officer, Naperville Law Firm
Fill the Gaps. Accelerate with Experts.
Even with strong internal teams, Chicago law firms often hit roadblocks, missing key skills needed for audits, client security requirements, risk assessments, or evolving compliance demands. That’s where Wingman steps in. With speed, flexibility, and deep expertise.
You get access to a team of CIOs, CISOs, architects, and engineers, each selected to meet the specific needs of your firm. This isn’t off-the-shelf support. Wingman brings peer-level legal tech expertise, practical guidance, and tailored roadmaps that empower your IT and security leaders to move faster and smarter, without expanding headcount.
Our Strategic Agile Approach
The Wingman service follows a proven six-step process that brings discipline and flexibility together.
This approach ensures consistent progress without overwhelming your team.
Get Started with Wingman
Transform Gaps into Momentum. Ready to turn IT and security from a constraint into a competitive edge?
Let’s talk about how Wingman can plug into your team, fill critical gaps, and drive your roadmap forward with the right expertise, at the right time.
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