Hello, I'm
Chris Cimaszewski
Baltimore, MD, USA
Software Developer - Technology Leader - Technical Architect Contact Me


code is art

My name is Chris Cimaszewski, and I solve problems with technology. I'm a seasoned software developer, architect, technical manager, and entrepreneur with over a decade of professional experience. I'm passionate about making life easier through software. My software has impacted millions of users across the following industries:


I help to define, and also implement, national healthcare interoperability standards. On behalf of the Office of the National (ONC), I am the technical architect and lead engineer for the Standards Implementation and Testing Environment (www.sitenv.org). For SITE, we create and host the necessary test tools to allow Health IT software product vendors to test their systems for Meaningful Use. I also lead a team of engineers that are working with NIST to create future Meaningful Use certification test tools.


My expertise lies primarily in the tolling industry. I have designed and developed the full stack (lane controller, data aggregation services, and toll host clients) of software required to implement electronic toll collection (ETC) and conventional lanes. I have also developed violation imaging and video auditing systems to support my toll road implementations. Aside from tolling, I also have experience with spatial software including traffic management systems and straight-line diagramming tools, to assist state and regional transportation departments.


I have played the roles of both software and enterprise architect for one of the largest student loan servicers in the country. I designed many of their SOA components (e.g. identity verification, account management, document management) as we migrated their enterprise away from legacy mainframe systems. I'm also well versed in the PCI DSS information security standard, and I have implemented various systems that have passed formal validation of this standard. Finally, I was the lead technical architect for a loan origination SaaS product, which focused primarily on the origination of private student loans.

I enjoy making beautiful and accessible software. I'm a firm believer that code is art. I have been a GNU/Linux user/zealot for 20 years, and I actively contribute to the open source software community; many contributions can be found on my GitHub page.

What I


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Where I
Do It

  • August 2017 to Present

    Chief Architect

    Baltimore, MD
    After a brief spirit journey, I started doing some R&D consulting for special projects at Ai. My early focus was with working with the team on the Unified Landing Page (ULP) product designing and implementing the identity access and management (ULP IAM) module. This module allows the product to support single-sign on from various external identity providers to the ULP portal and federate those authentication and authorization sessions to downstream applications, or service providers, through a mechanism called identity provider chaining, using AuthN/AuthZ standards such as SAML 1.0 and 2.0, OAuth 2.0, and OpenID Connect.

    From this R&D work, the leadership team at Ai worked to build me a new role within the organization in which I could focus on strategic initiatives (such as our cloud adoption strategy), lead our enterprise architecture, design and develop new R&D initiatives to determine market viability, and operate in a developer advocate role as a coach and mentor to our growing engineering team to help them adopt containerization, CI/CD processes, and cloud-native architectures.

    In mid-2018, there was a need for me to move back into an interim role, where I directly managed the engineering team again, and actively played a solution architect/scrum master role for one of our development teams to establish CI/CD workflows and pipelines for our products and help get through some critical delivery milestones. I moved back to my chief architect/developer advocate role in June of 2019.
  • June 2013 to May 2017

    Principal, Engineering

    Baltimore, MD
    I served a leadership role in the company as well as a solutions architect. While I was in this role at Ai, I've helped to make some positive change in the company. We doubled our staff from just under 30 employees to over 60 in my first 18 months. I was part of a three person team that devised a new software engineering process (based on Scrum) that has been appraised at CMMI level 3, and we also successfully migrated all of our development projects to this process. I also serve as the technical architect overseeing some of our CRISP engineering projects (e.g. the CRISP Reporting System and a state-wide provider directory) and our entire federal engineering project portfolio. I still found some time to write some software for Ai, as well - I have developed the majority of the Standards Testing and Implementation Environment, and I'm responsible for UX design and Section 508 compliance. Fortunately, all of my development work for our federal contracts is released as open source, most of which can be found on GitHub.
  • October 2011 to June 2013

    Software Architect Consultant

    Mechanicsburg, PA
    Celerity had a solid relationship with many Central-PA based private and public organizations, and there was an opportunity to independently consult with them for the Architecture team at AES/PHEAA. While I was consulting at PHEAA, I architected many of their web applications and services; I focused primarily on their privacy and identity verification systems, I also helped to stand up their enterprise architecture team. By the end of my time at PHEAA, I had been selected to lead their legacy modernization effort to migrate their architecture away from mainframe systems. I taught Java and Object-oriented design/development methodologies to their mainframe development team, and I led the platform migration and productization effort of their private student loan origination SaaS product.
  • April 2009 to April 2011

    Senior Application Developer

    Camp Hill, PA
    I was recruited to Highmark by some former colleagues. While at Highmark, I focused on Java web application and service development, specifically with their Privacy and Compliance division. I was the Lead Developer/Architect, responsible for the design, development, and production support of multiple rich internet applications. I managed a team of Java and COBOL developers, and I migrated our team from a waterfall SDLC to an agile methodology (Scrum) utilizing Test-Driven Development. I worked closely with the enterprise architecture group in defining a new reference implementation for their JEE technology stack, and I led my team of developers in the adoption of the reference implementation in multiple projects. I also served as a mentor as other departments began to adopt the new technology stack.
  • June 2004 to September 2006

    Software Developer

    Mechanicsburg, PA
    At Target Systems, I worked my way up to a lead developer on various software engineering projects for their federal, state, and commercial clients.


In my free time, I try to keep my skills sharp and learn new technologies. As working products are created, I release the code in hopes to inspire people to learn development. Code for my projects can be found on my GitHub page.


Portsmouth is an enhanced window manager for Mac OSX. The current version should be compatible with Mountain Lion, Mavericks, and Yosemite.

With Portsmouth, you can automatically resize and position windows (both Cocoa and X11) via a keyboard shortcut or dragging and dropping the window to a target on the screen (corners and edges). Window resizing and positioning is supported by all Cocoa-based and X11-based applications.

Additional Functionality:

  • Keyboard controlled window resizing and positioning
  • Keyboard controlled screen lock and screensaver activation
  • Fully customizable interface

Portsmouth is released as open-source software and is available from the GitHub repository.