Matthew Williamson
Founder & CEO, Clevyr · Enterprise Technology Strategy · AI, Software Engineering & Intelligent Systems
Oklahoma City, OK · clevyr.com · Clevyr on infocard · crossinginto.ai
About
I’m the founder and CEO of Clevyr, a technology engineering and consulting company headquartered in Oklahoma City. I’ve spent more than 30 years working at the intersection of software, infrastructure, business, and emerging technologies.
At Clevyr, we help organizations solve difficult problems through custom software engineering, systems integration, artificial intelligence, data architecture, cybersecurity, and intelligent automation. Our work spans enterprise platforms, business-critical integrations, and the increasingly complex intersection of humans and AI agents.
I’m particularly interested in what happens when AI evolves beyond individual tools into coordinated systems capable of transforming how organizations operate.
I still build things. Not because I need another startup, but because experimenting is how I learn, challenge assumptions, and stay connected to the technology.
My focus remains Clevyr, our clients, and building the next generation of intelligent business systems.
Clevyr
Humanizing the technology experience.
Clevyr helps organizations understand, design, integrate, and operate the technology their businesses depend on. We’ve done it since 2009 — through early web platforms, enterprise integration, cloud, and now AI — with thoughtful engineering, sound architecture, and technology that serves people.
Organizations bring us in when the problem is bigger than a single tool: systems that don’t talk to each other, operations that have outgrown off-the-shelf software, data no one trusts, or an AI strategy that needs to become something real and accountable.
| Capability | What it means |
|---|---|
| AI Strategy & Implementation | AI roadmaps, applied AI in real workflows, agentic systems and orchestration |
| Custom Software Engineering | Customer-facing platforms, internal systems, mobile applications |
| Enterprise Systems Integration | APIs and integrations between business-critical systems |
| Data Engineering & Intelligence | Data architecture, analytics, business intelligence, intelligent automation |
| Cloud Infrastructure | Cloud architecture, DevOps, and ongoing operations |
| Cybersecurity | Security practices and technology governance |
| CRM & RevOps | HubSpot Diamond Solutions Partner — CRM architecture and revenue operations, with capabilities well beyond HubSpot |
Industries: Banking & financial services · Healthcare · Energy · Logistics · Education · Pro sports · Non-profits
Working with Clevyr
I’m not seeking employment, freelance programming work, or personal consulting engagements. If your organization needs help with software, integration, data, or AI, talk to Clevyr — that’s where the work happens, with a senior team behind it.
I’m glad to connect with enterprise technology leaders and potential strategic partners, and I’m open to speaking and advisory opportunities.
Expertise
- Enterprise Technology Strategy & Architecture
- AI Strategy, Agentic Systems & Orchestration
- Custom Software Engineering & Systems Integration
- Data Engineering, Business Intelligence & Automation
- Cloud Architecture, Infrastructure & DevOps
- Cybersecurity & Technology Governance
- HubSpot, CRM Architecture & Revenue Operations
- Executive Leadership, Business Development & Organizational Strategy
What I do best is understand complex organizations — find the architectural and operational problems underneath the symptoms, then build the teams and systems that solve them.
Experience
Founder & Chief Executive Officer
Clevyr, Inc. · Company profile
Mar 2009 – Present · 17 yrs
Oklahoma City, OK
- Founded Clevyr and have led it for 17 years as an engineering organization — not a small software shop or a single-platform agency.
- Set company strategy, enterprise architecture direction, and the delivery model behind every engagement.
- Led large-scale, complex initiatives including logistics centers, laboratory management systems, and critical business infrastructure for Fortune 100 companies.
- Built Clevyr’s capabilities across custom software, systems integration, data engineering, cloud infrastructure, cybersecurity, and CRM/RevOps, and earned HubSpot Diamond Solutions Partner status.
- Leading Clevyr’s work in AI strategy and agentic systems — helping clients move from AI experiments to accountable, integrated systems.
We are here to help each other, and that is what drives me.
Earlier experience (1992–2009)
Technology Strategist
iThryv · Full-time
Sep 2008 – Apr 2009 · 8 mos
Oklahoma City Metropolitan Area · Hybrid
After introducing two of my favorite technologists, they combined forces to create this early financial services corporation to create online banking replacements for most major cores. I managed internal web development along with the marketing website, day-to-day project management of the software development team, and more.
Marketing Internet Strategist
Century Martial Arts
May 2007 – Oct 2008 · 1 yr 6 mos
Ran the e-commerce platform for the world’s largest martial arts gear manufacturer. Handled all SEO, CPC, sales, placement and more.
Corporate Internet Strategist
Metavante
Mar 2002 – May 2007 · 5 yrs 3 mos
Joined Advanced Financial Solutions and ran a group of motivated developers, oversaw all SEO marketing, acted as a project manager on IT initiatives. We were acquired by Metavante.
Java Developer
American Fidelity / Enrollcom · Full-time
Aug 1999 – Mar 2002 · 2 yrs 8 mos
Oklahoma City Metropolitan Area · On-site
Hired to create the initial software offering and infrastructure built on top of a Solaris/Java stack using the BEA WebLogic suite of servers. I focused on UI/UX java development once the initial DevOps was built out.
Director of Content
LifeLine · Full-time
Apr 1998 – Aug 1999 · 1 yr 5 mos
Oklahoma City Metropolitan Area · On-site
Built the webservers for this startup using Solaris and Apache. I also managed and curated the content for this Christian internet provider focusing on family-friendly content.
Electronic Media Editor/Web Developer
NewsOK.Com · Full-time
Jan 1996 – Apr 1998 · 2 yrs 4 mos
Oklahoma City Metropolitan Area · Hybrid
Hired as the first employee of ConnectOK and NewsOK.com to facilitate the creation of the state’s largest newspaper’s online presence. I worked with a small team to move the daily newspaper onto the web utilizing the Netscape Suite of E-Commerce products and extensive custom development on the Harris Publishing System.
Field Artillery Cannoneer
United States Marine Corps · Part-time
Jan 1992 – Jul 1996 · 4 yrs 7 mos
- Operated the M198 artillery system as a Field Artillery Cannoneer in the US Marine Corps Reserves.
- Managed the deployment of the SAW and PRC-77 communication equipment during exercises.
- Collaborated with team members to ensure effective artillery support and communication in various scenarios.
Assistant Sales Manager
ioNET DBA Internet Oklahoma
Jul 1995 – Jan 1996 · 7 mos
Oklahoma City Metropolitan Area
I was promoted from the technical side into sales to help spur significant contract development and client success. I joined this ISP startup and gave it my life for a year, one of the best years of my professional career. It was a Master’s Class in network topology, UNIX, and the web.
Internet Technician/Solaris Developer
ioNet (Internet Oklahoma) · Full-time
Jan 1995 – Jul 1995 · 7 mos
Oklahoma City Metropolitan Area · On-site
As the first employee of ioNet, I helped to build the groundwork for what would become a regional player in the early internet. From punching down phone lines and provisioning thousands of modems to running Apache, SendMail, WuFTP, Gopher, WAIS, and more, this was a Master’s Class in the internet before most knew what it was.
Technical Background
My career started in 1995 as the first employee of an Oklahoma ISP — punching down phone lines, provisioning modems, and running UNIX servers before most people knew what the internet was. I’ve worked across modern and legacy stacks ever since.
| Area | Experience |
|---|---|
| Infrastructure | UNIX/Solaris, Apache, networking & ISP operations, cloud & edge platforms (Cloudflare Workers, D1, KV, Durable Objects) |
| Languages | TypeScript · JavaScript · Java |
| Frameworks & Platforms | Vue · React · Astro · Hono · BEA WebLogic · Netscape commerce suite |
| AI | Anthropic Claude · OpenAI · Workers AI · agent workflows and orchestration |
| Business Systems | HubSpot · CRM & RevOps architecture · e-commerce · content management |
Personal Experiments & Technical Exploration
I believe technology leaders should remain curious about the technologies they’re asking others to adopt. Outside my work at Clevyr, I build small applications and experimental platforms to explore AI, agentic architectures, infrastructure, and emerging development tools. These are personal learning projects, not separate business ventures.
Crossing Into
My personal site and independent publication on AI
A place to make sense of our transition into an AI-shaped world, and decide how we want to cross it. Home to The Brief — a five-minute weekday briefing on consequential AI news, research, policy, and arguments — and a set of free, open tools that make websites and AI systems more legible, accountable, and useful: the llms.txt generator, Legible, Aligned, izakaya, ChainProof, and Eigenstate.
infocard.ai
Exploring: AI tag extraction and search over plain Markdown
Markdown resumes from GitHub repos — no accounts, no keyword stuffing. Recruiter search with AI tag extraction, skill matrix, and company profiles.
typescript hono cloudflare-workers d1 workers-ai
chainproof.ai
Exploring: trust and accountability for AI agents
A signed, hash-chained ledger for agentic workflows. Every AI action is cryptographically logged with a verifiable audit trail.
typescript hono cloudflare-workers d1 durable-objects
promptcard.ai
Exploring: how individuals and teams manage prompts day to day
Store, organize, search, and share AI prompts. Folders, tags, full-text search, keyboard shortcuts, and team folder sharing.
typescript cloudflare-workers
briefing.wtf
Exploring: fast, algorithm-free information on the edge
A global news start page — 43 feeds, 8 categories, and a live market ticker, with no algorithmic noise.
typescript cloudflare-workers