Fractional Architect · Strategic Advisor · Expert Witness

Designing solutions that workeffortlessly.

I help teams untangle complexity in software systems: modernizing aging platforms, scaling cloud-native solutions, making a platform work for AI coding agents, and explaining technical decisions in high-stakes legal cases.

Chris Woody Woodruff
  • Microsoft MVP 2025
  • JetBrains Community Contributor
The problem

Your system has outgrown the people who can hold it in their heads.

Architecture decisions get deferred or re-litigated every sprint. A migration, a rewrite, or a lawsuit is on the horizon. A full-time principal architect is the right role, but not the right spend yet.

The solution

Senior technical judgment, on the schedule the decision actually needs.

Fractional architecture, a 90-minute decision brief, a fixed-fee assessment, expert testimony, or a seat at the board table. Every engagement ends with written decisions your team can point to and push back on.

Hi there

I'm Woody. Allow me to introduce myself.

After two decades building distributed systems with .NET, C#, and Azure, I've shifted from full-time execution to strategic impact. Today I work as a fractional architect, technology advisor, and software expert witness, offering focused expertise exactly when and where it's needed.

I'm a Microsoft MVP (first awarded in 2008), co-host of The Breakpoint Show, author ofASP.NET Core Reimagined with htmx and Beyond Boundaries, and the person who coined the term Agentic Developer Relations. As AI writes more of the world's software, the scarce skill is knowing what not to build.

About me

Heard and read on

  • .NET Rocks!
  • JetBrains
  • InfoWorld
  • TechBullion
  • The Azure Podcast
  • CDF

All press and media

The numbers don't lie

Notable milestones from a career that started before the first .COM boom

  • 25+Years building software
  • 50+Conference talks, North America and Europe
  • 200+Articles on this blog
  • 3Books written or in print
What I do

I focus on the architecture so you can focus on the business.

Embedded architecture leadership, forensic code analysis for litigation, agentic developer relations, scoped modernization projects, and an independent technical voice for boards and founders.

See the six services
How I do it

Discovery, engagement, execution, iteration.

  1. Discovery. We define your goals, pain points, and existing tech landscape in a focused kickoff.
  2. Engagement. I embed with your team on a fractional basis: guidance, architecture reviews, decision support.
  3. Execution. Clear deliverables and actionable recommendations, backed by experience and empathy.
  4. Iteration. As your needs evolve, so does my involvement: deeper during transitions, lighter when stable.
Testimonials

Some love from clients

I had the pleasure of working with Chris on several projects for one of our key clients. Chris is a true professional. His technical skills are expert level. Chris is a strong team lead who goes above and beyond to ensure his team’s success. If you have an opportunity to leverage Chris in your organization, I would highly recommend him.

Natalie GreenwoodGlobal Senior Director of Advisory Services

Chris brings a rare combination of deep technical expertise and clear communication. His ability to translate complex architectural concepts into actionable guidance makes him an invaluable resource for any team.

Ted NewardArchitect / Leader
Blog & Insights

Useful articles from the blog

All blog posts

Let's connect

Ready to untangle your system?

Whether in the boardroom or the courtroom, I bring clarity to complex software challenges and help people make better decisions through better understanding.

Hire me