IT Support for Creative Professionals

We Are an Apple Authorized Premium Service Provider Offering

  • Mac-based IT Support
  • Systems Design
  • Remote Support
  • Consulting
  • Outsourced CIO
  • Data Security
  • Network Administration & Maintenance
  • Hardware & Software Setup

About Chesa Creative IT

Who We Are

Chesapeake Systems Creative IT offers hands-on, expert-led systems design and management, outsourced IT and consulting for small to mid-size businesses and departments in the Baltimore, MD to Washington, DC area. Chesapeake IT is Apple Authorized and brings more than 25 years of experience working with Mac-based clients, network support, data security, backend technology development, and much more.

What We Specialize In

Whether you need remote support, expert opinion on the best storage solution for your business, reassurance that you’ve got ironclad security in place, a ground-up system build, recurring maintenance, or to hand off all IT duties without ever looking back, we are ready to meet you where you are. Chesa IT is the first call for systems design, implementation, and support.

Our Process

We’ve made it our business to know our clients inside and out, and our mission is to advance their business objectives through technology. Chesapeake IT clients depend on us to make sure the user experience is seamless and efficient, systems are reliable and secure, and you don’t lose revenue to downtime. It’s our job to make sure your business runs smoothly.

Our Services

Outsourced CIO

The right IT infrastructure starts with the right plan. Our experienced CIO’s act as a part of your team, and are there to help architect and deliver and IT roadmap for success that makes sense for your organization, your budget and your users.

Managed Services

Managed services encompasses almost everything we do for our clients on an ongoing basis. We ensure your network, hardware, software, and overall IT platform is secure, compliant, and performing at a high level. If issues or questions pop up, our team is there to help.

Hardware & Software Setup

Buying an Apple product from Best Buy or the Apple Store may seem like an easy thing, but for most companies the devil is in the details. User management, software installation and updates, modified hardware requirements – as an Apple Authorized Service Provider, Chesapeake can order, assemble and deliver any Apple product you need so it’s ready to use when your team walks in the door. For one device, or hundreds – we’ve been an Apple partner for over 10 years.


Working as an extension of your creative teams, and in tandem with IT, Chesapeake Creative IT consultants are the experts in IT who can assess your infrastructure in light of all internal and external considerations, creating a plan that allows you to grow to meet tomorrow’s demands.

Network Administration & Maintenance

It can be easy to forget that it’s not just the computers that keep your office working.  Under the desk, through the walls, in a closet and in the the air, your company’s network is your lifeline to the world.  Chesapeake will keep your organization’s network up-to-date, secure, and operating as intended.

Data Security

The machines are beautiful, but the data is irreplaceable. The team at Chesapeake will ensure that your organization’s data is backed up and secure wherever your users go, and protect against those who would try to steal your data for their own purposes.

Who We Help

  • Schools + universities
  • Architecture Firms
  • Financial Institutions
  • Creative Agencies
  • Small Business
  • Hospitals and Physicians
  • Startups

The Problem

Chesa has been providing our services to The Walters Art Museum for over 15 years. Once every two months our team goes in and provides maintenance and consulting services. Their organization has a variety of unique challenges that our team is happy to help determine solutions for.

Our Solution

Everything that comes into the museum gets photographed – their team has to capture and document everything they do, including visiting collections, and their collections. We implemented a solution to keep their photographs backed up. Our team works side by side with their IT Director to accomplish their organizational goals for Macs, and performs regular ongoing maintenance for the marketing department, photographers, and any other staff in need of support.

The Problem

Another IT company referred Water Street Design to us because they couldn’t meet their industry specific needs, and work with their Mac systems. They had been working with Mindspring previously, and wanted to transition to an MS Exchange back end.

Our Solution

Rather than trying to shoehorn in a new solution, we picked up and supported what they had. Their agency is all Mac and uses Adobe Creative Cloud. Our team goes to their office once a month and spends half day to a day performing maintenance on each workstation. We also use software that gives us and them insights into how their machines are performing, as well as  provide remote and phone support calls whenever they run into any problems with Adobe software or any of the other tools they use. When the team needs a new machine we take care of all hardware – networking, wireless, Mac, PC, data backup, etc. “I’ve been really pleased with the service from Chesapeake Systems. We are a mac-based creative agency, and until we worked with Dave and his company, most IT consultants came at our mac-OS problems with Microsoft-style solutions… it just didn’t work. Chesapeake doesn’t just support our network operating system, they also understand all the tools we use, and how vital things like font management and printer definitions are to the success of our business. Managed IT is a great solution for small businesses like mine. Remote monitoring and software updates coupled with monthly on-site “wellness visits” have all but eliminated lost time for computer related problems.” – Water Street Design

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Chesapeake Systems