/about

Kevin Willoughby III

i solve problems by designing systems that don't need me.

What I do

I design systems that reduce complexity and make work flow better. That includes automation, internal tools, and decision frameworks — the quiet infrastructure that keeps everything moving.

I specialize in high-friction environments: unclear goals, overlapping priorities, systems with no documentation. That's where I operate best. By breaking inertia and turning ambiguity into action.

I work where things are messy, to make them less so. Most people don't notice the systems I build. And that's the point.

Background

I didn't grow up with consistency. There wasn't a clear path or someone showing me how things work — I had to figure that out by watching, breaking, and rebuilding. Everything I've built came from two things: needing stability, and refusing to wait for someone else to give it to me.

I got obsessed with systems because life felt chaotic.
I got obsessed with speed because I didn't trust anything to last.
And I got disciplined because, honestly, I was scared of falling behind.

There is no clean story. Just a pattern: I find the gaps, I fix the friction, and I keep moving.

Philosophy

I don't believe anything matters by default. That used to scare me.

If nothing has meaning built in, I get to choose what does. So I choose to build, to move with clarity, and to create systems that make things better — for myself, for others, for whatever comes after me.

I don't rely on motivation or emotion to move. I work with whatever's in front of me, and I try to leave things smoother than I found them.

I don't think I have it all figured out. But I do know how to keep going — calmly, intentionally, without pretending it's deeper than that.

Professional Experience

Software Delivery Manager

Sentry Management Inc. | 2024 - Present

Took ownership of a legacy system mid-transition. Migrated infrastructure from CentOS 6 to RedHat 8 to stabilize and secure our environment.
Rebuilt our internal tools platform: restructured 90% of the UI/UX and rewrote how users interact with the system across the org.
Set up structured product management where there was none — introduced Azure DevOps + Aha!, standardized backlog flow, clarified priorities across engineering and ops.
Automated manual admin tasks to reduce wasted time. Saved 40+ hours/month in repetitive work.
Overhauled our payment operations — replaced 1,000s of manual entries with a reliable automated process that brought revenue and reduced errors.
Currently building out a scalable integration layer for our banking systems to handle future growth without tech debt stacking.

IT Support & Automation Specialist

Sentry Management Inc. | 2022 - 2024

Rebuilt the company's Zendesk instance used by 300K+ clients — improved structure, ticket routing, and visibility across teams.
Built and deployed a custom health-monitoring and sync system (Azure, LDAP) to reduce manual provisioning issues.
Wrote internal tools and scripts to improve onboarding speed and reduce setup errors.
Acted as the connective tissue between users and developers — cleaned up the handoff process, clarified technical feedback, and kept requests flowing cleanly into delivery.

Co-Founder & Technical Lead

Quantera | 2018 - 2021

Co-founded and ran a dev shop serving 150+ clients globally. Focus on systems that automated or enhanced client workflows.
Delivered full-cycle projects: chatbots, dashboards, admin tooling, integrations, and backend infrastructure.
Handled architecture, coding, deployment, and client relations.
Clients came to use with messy ideas — we delivered clean solutions they kept using.

Contact

Let's cut the friction. kevin@kvnw.dev

Or skip the small talk — book directly.

You don't need a cold email. You need a warm launch point.