About Chesapeake Systems

Where strategy meets execution

We've been where you are—leading complex IT initiatives, navigating stakeholder dynamics, and driving outcomes that matter. That experience shapes everything we do.

Built on real-world experience

Chesapeake Systems was founded on a simple observation: too many IT initiatives fail not because of technology, but because of the gap between strategy and execution. We bridge that gap.

Our leadership has spent decades in the trenches—managing $100M+ enterprise implementations, leading technical teams through complex design, implementations and migrations, and helping executives navigate critical decisions. We've seen what works, what doesn't, and why.

Based in Baltimore, we serve clients across healthcare, federal, and commercial sectors. Whether you need strategic guidance before a major initiative or hands-on program leadership to drive it home, we bring the expertise and commitment to make it succeed.

We've built our practice around solving the pain points we've seen too many times: organizations wasting time and money on firms that staff projects and full time employees with inexperienced recruiters and account managers who are learning on your dime. Our approach is different. We bring senior practitioners with real-world experience from day one, streamline decision-making through proven frameworks, and cut through the inefficiencies that plague traditional consulting engagements. The result: faster time to value, lower total cost, and outcomes that actually stick.

20+
Years Experience
$100M+
Programs Led
50+
Clients Served
100%
Repeat Clients

Partnering with Chesapeake Systems provided us a unique combination of strategy, IT expertise and excellent project management to keep it all organized that provided us exponential value.

Principal

Lobbying Firm — Healthcare & Federal Sector

How we think about work

We combine structure with adaptability, bringing the right expertise to each engagement while staying responsive to what the work actually needs.

Clarity First

We help you understand the full picture before making decisions. No jargon, no unnecessary complexity—just clear thinking about what you're trying to accomplish and how to get there.

Structured Flexibility

We bring waterfall planning to set direction and agile execution to adapt as we learn. Clear milestones, but room to iterate based on what we discover along the way.

Right-Sized Teams

We match expertise to the initiative. Sometimes that means a single advisor; sometimes it means a full program team. You get what you need, not a predetermined staffing model.

Who's behind the work

Brian Reno, Founder & Principal of Chesapeake Systems

Brian Reno

Founder & Principal

Brian founded Chesapeake Systems after two decades leading enterprise IT initiatives across healthcare, federal, and commercial sectors. His experience spans the full spectrum—from strategic planning and vendor selection to hands-on technical program management.

He has led technical delivery for $100M+ Epic implementations, managed enterprise Microsoft 365 migrations, and managed the SharePoint platform at CMS. He has chaired steering committees in both federal and healthcare sectors, guiding cross-functional teams through complex decision-making. His commitment to team development earned him a nomination for employee engagement excellence at Johns Hopkins Medicine, and he serves as a member of a leadership council for technology consultants. His work in emerging technology includes leading quantum computing initiatives with DoD contractors and developing AI-powered platforms for vertical markets.

Brian's approach is shaped by having been on both sides of the table—as the client trying to make sense of vendor recommendations, and as the consultant responsible for making initiatives succeed. That dual perspective informs how Chesapeake Systems works: clear communication, realistic planning, and a relentless focus on outcomes.

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Ready to talk?

Whether you're planning a major initiative or need help with one already underway, let's discuss how we can help.