Modernization Planning Should Be Continuous
Why Stackryn Exists
Enterprise modernization is one of the most expensive initiatives an organization undertakes — yet the planning that precedes it still runs on fragmented engagements, static documents, and outputs with a short shelf life.
Organizations spend hundreds of thousands — sometimes over a million — to answer three questions that go stale almost immediately:
- What systems do we have?
- What should we build or change?
- Are we building the right thing?
Stackryn replaces that model with a living, AI-powered platform that answers them continuously.
Built by people who have served and built.
STACKRYN is a veteran-founded and veteran-led technology company focused on improving how organizations move from intent to delivery.
Who We Are
A founding team shaped by military service, entrepreneurship, and shared love for tech — with deep experience across enterprise SaaS, government and national security modernization, healthcare, financial services, litigation, retail, AI/ML, and startup delivery.
Co-Founder & CEO / CTPO
Army & National Guard Veteran · Enterprise Modernization Leader
Creator of the Stackryn platform and an enterprise modernization leader with 15+ years architecting large-scale transformations across regulated, distributed environments. Led a 0→1 consolidation of 15 legacy systems into a unified enterprise platform supporting 25,000+ users — governed by 2,000+ structured requirements that exposed exactly where alignment breaks down between executives, business stakeholders, and delivery teams. Built Stackryn to solve that gap upstream, drawing on experience advising senior leadership on secure, SaaS and AI-ready adoption in complex, regulated environments.
Co-Founder & COO
Air Force Veteran · SaaS Sales & GTM Strategist
Enterprise Solution Engineer with 15+ years helping organizations evolve and unlock efficiencies through state-of-the-art technology. Passionate about uncovering technical solutions to complex business problems and aligning stakeholders, delivery teams, and engineering around a single source of truth — the exact problem Stackryn solves upstream of Jira and ADO. Air Force veteran focused on bridging executive intent and technical execution before a single backlog item is written.
Soon
Chris Gibson
Co-Founder & CGO
Entrepreneur · Growth & Operations Strategist
Serial entrepreneur with 30+ years building and scaling startups, including three successful exits across diverse industries. Brings the operational backbone Stackryn needs — leading contracting, finance, accounting, and back-office strategy — while partnering with the team on growth planning, go-to-market execution, and long-term positioning. Pattern-matches early-stage chaos into repeatable systems, ensuring the company is structured to scale the moment the market is ready.
Our Commitment
Alignment
Clients and integrators start every engagement with shared understanding.
Clarity
Living intelligence replaces static decks that age the moment they ship.
Governance
Structured handoffs into Jira, ADO, and Jama — no rework, no drift.