About Me
I help teams untangle complexity in software systems—whether it's modernizing aging platforms, scaling new cloud-native solutions, or explaining technical decisions in high-stakes legal cases.
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 work with companies navigating change—platform rewrites, cloud transitions, or critical architecture decisions. I also support legal teams and litigators with technical assessments, codebase analysis, and expert opinions in software-related litigation.
Full Name
Christopher Woodruff
Email Address
chris@woodruff.dev
Phone
+1 616.724.6885
services
Essential Services
Bring seasoned architectural strategy to your team when you need it most, from roadmap to execution.
High-impact technical leadership—without the full-time overhea
Ongoing architecture support, available when your team needs clarity, feedback, or direction.
Trusted guidance on call—because tech challenges don’t follow a schedule
I lead and execute focused architecture and modernization efforts with start-to-finish accountability.
Clear deliverables, defined outcomes, real momentum
Unbiased, expert analysis of software systems for litigation, IP disputes, and contract breakdowns.
When code is on trial, I help make the technical case clear
I advise leadership teams on platform evolution, scaling, technical risk, and innovation.
Strategic tech insight where it matters most—at the decision table
Fast, focused sessions to resolve architecture questions, performance issues, or critical forks in the road.
One hour. One problem. Real answers
testimonials
Users Feedback
“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. Chris is highly sought after by industry experts and is in high demand. If you have an opportunity to leverage Chris in your organization, I would highly recommend him.”
Natalie Greenwood / Global Senior Director of Advisory Services
“ User feedback is qualitative & quantitative data from customers on their likes, dislikes ”
Ted Neward / Architect/Leader
“ Impressions, and requests about a product. Collecting and making sense of user feedback is critical. ”
Dekson P. Pablo / CEO At Brator
call to action
Any Project On Mind
Whether in the boardroom or the courtroom, I bring clarity to complex software challenges—and help people make better decisions through better understanding.
Let’s work together to solve what’s slowing you down.
Address : Wyoming, MI 4941
Phone : +1 616.724.6885
Email : chris@woodruff.dev
news
Blog & Insights
Business of Software
Software Quality Assessment as an Ongoing Practice, Not a One-Time Event
If you're looking to enhance your organization's systems through quality assessments, I would love to connect with you. Let's explore how I can contribute to your success. You can easily reach me via my contact page here: https://www.woodruff.dev/contact/ Quality checks are often treated as a box to...
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Business of Software
The Hidden ROI of Technical Due Diligence in Software Investments
If you're looking to enhance your organization's ROI through strategic software investments, I would love to connect with you. Let's explore how I can contribute to your success. You can easily reach me via my contact page here: https://www.woodruff.dev/contact/ Most investment decisions focus on fi...
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Simplicity-First
Bringing Simplicity-First to the Page: My Upcoming Book
I am excited to share some big news. In the second half of 2026, my new book, titled Software Architecture Made Simple: A ‘Simplicity-First’ Approach to Software in the Age of Complexity, will be released. This book compiles years of blog articles, newsletters, and social media post...
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Business of Software
System Modernization Without the Burnout: Lessons from Distributed Systems
If you're looking for support in successfully migrating your legacy system, I would love to help your organization through this process. Let's connect and explore how I can assist you. You can contact me directly via my contact page here: https://www.woodruff.dev/contact/ The Dreaded “Big-Bang...
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Business of Software
Why Fractional Architecture is the Future of Technology Strategy
If you’d like to chat about how I can help your organization as a Fractional Architect, I’d love to connect. You can reach me directly through my contact page here: https://www.woodruff.dev/contact/ Hook: The Myth of Big-Enterprise Architecture For years, software architecture has carrie...
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Genetic Algorithms
Day 35: Evolution Beyond Biology: Using Genetic Algorithms for Creative Art and Design
Genetic Algorithms are often associated with engineering, scheduling, or optimization problems, but their potential extends into the domain of art and design. When applied to visual composition, generative structures, or music synthesis, GAs can produce unexpected and compelling outcomes. These crea...
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