About Me

Hi, my name is Darryl Anderson, and I provide technology advisement and design and development services to early and growth stage software companies. Based in Chicago, IL, I primarily work with companies in the local market, but can also work with remote companies.

I’ve been building software products for 20+ years, across multiple domains including healthcare (genomics, clinical trials, medical records), transportation, knowledge management, and telecom.

From a technology perspective, I’m passionate about cloud architecture, continuous delivery, devops culture, and security. I believe that architecture should support the business, and that common architectural ‘ilities’ such as reliability, scalability, maintainability, security, and extensibility are best achieved through cloud delivery models.

Learn more about me at the links below:

LinkedIn GitHub Mastodon


  • Cloud architecture and devops advisory engagements.
  • AWS, Azure, and Google Cloud contracts.
  • Technical architecture guidance.
  • Security reviews and advisory services.


I have 20+ years of experience in building large scale enterprise web applications.

I currently serve as Principal Architect for Clearcover, a hyper growth insuretech startup where I lead the Architecture, Data Engineering, and SRE/Cloud Ops teams.

Prior to joining Clearcover, I was the co-founder of ChainFront, a blockchain services company.

Before that, I was Chief Architect and Technical Advisor for project44, a rapid growth startup in the transportation logistics space.

Prior to joining project44, I was the lead architect for Oracle’s Healthcare Global Business Unit. I was responsible for the architecture and development of Oracle’s Translational Research, Precision Medicine, and Healthcare Analytics product suites. These products combine genomic data with clinical data for research and point-of-care solutions.

I came to Oracle through the acquisition of ClearTrial, where I was the founding architect. While at ClearTrial, in addition to building the technical architecture, product development processes, and software development infrastructure, I built the SaaS hosting platform, achieving 99.9995% planned uptime since launch in 2006.

Prior to ClearTrial, I was the lead software architect at Participate.com, a knowledge management SaaS company. Acquired by OutStart Inc.

Prior to Participate.com, I was the lead software architect at MedRemote, a medical transcription SaaS company. Acquired by Nuance.

I have a Masters degree in Electrical Engineering from University of Waterloo in Canada.