Developer • USMC Veteran • Lifelong Learner

Judah
Helland

I’m a developer who ships practical software for real ops workflows — AI agents, support tooling, and the glue that makes them trustworthy. I communicate clearly, own the work, and keep getting sharper.

How I show up

I care about steady execution more than flashy claims. My focus is writing maintainable code, asking good questions, and creating momentum for the team.

About Me

Hands-on builder,
eager to keep growing.

I spent nearly four years in the United States Marine Corps as a Network Administrator, supporting mission-critical environments where reliability and accountability were non-negotiable.

After the Corps, I worked in technical support, then transitioned into software. That path gave me a practical mindset: solve the real issue, communicate clearly, and leave systems better than I found them.

"I bring discipline and consistency now, and I’m hungry to learn from stronger engineers every day."

Today I build AI systems and SaaS tools with TypeScript, React, and Cloudflare — especially products that sit where tickets, devices, and techs already work. I’m aiming for a role where I can contribute immediately while growing into larger ownership.

Experience highlights:

• USMC Network Administrator (2018–2022): operations, maintenance, and team leadership.

• Technical Support (~3 years): high-volume issue resolution and process improvements.

• Software Developer (present): AI agents, MSP tooling, and production SaaS on Cloudflare.

What I’m optimizing for: durable systems, clear ownership, and AI that earns its place in a workflow.

Selected Work

Projects & Deep Dives

Two AI systems for MSP ops: Caisey puts a troubleshooting agent on the endpoint; Steno keeps ticket write-ups honest after the work is done.

01
AI / MSP Ops
React / TypeScript Workers + DOs Clerk
Caisey
Remote troubleshooting console — cloud UI coordinating headless agents on client machines
Problem
MSP techs need on-device investigation without brittle remote sessions, and orgs need audit, permissions, and installers outside the browser.
Solution
Built a control plane to enroll devices, pick a machine, and chat with a runtime that can investigate on-device — with org auth, audit trails, and installers on Cloudflare.
Clerk org Worker + DOs Bridge Endpoint runtime
Open architecture notes

Org-scoped fleet with manual deploy, auto-enroll, or client-specific installers. Runtime traffic is proxied for forward-only audit and conversation records. Permission defaults, Fast-mode controls, and multi-device prompts keep technicians in charge while the agent does the digging.

02
AI / Ticket Quality
Workers / D1 Astro Syncro API
Steno
Documentation quality agent — cron-driven AI that reopens thin Syncro tickets before they rot
Problem
Resolved tickets often skip root cause, steps, fix, and follow-up — knowledge that future techs need disappears into the void.
Solution
Every few minutes Steno scores recently resolved tickets, stamps a clean summary when they’re solid, or sends them back with a precise gap note techs can act on.
Syncro resolve Steno cron LLM audit Reopen / seal
Open implementation notes

Confidence thresholds and reopen caps keep noise low. Per problem-type expectations replace one blunt checklist. Teachable in-ticket tags (##STENO_UPDATE##, ##STENO_EXPECT##, ignore tags) let techs shape behavior without touching the Worker. Dashboard + runtime on Cloudflare with D1-backed state.

03
SaaS / Infrastructure
TypeScript / React Next.js Cloudflare
Microtunnel
Secure tunnel management without traditional VPN friction
Problem
Managing secure access for distributed teams was slow, brittle, and hard to audit.
Solution
Built a central UI for provisioning and controlling cloud tunnels with sane defaults and cleaner ops workflows.
Open architecture notes

Designed around a thin API layer and deterministic setup flows so support staff could handle onboarding without deep infrastructure knowledge.

04
Consumer / AI
Alpine.js Workers AI Cloudflare Pages
TewDew AI
Goal-to-task decomposition for people who hate blank to-do lists
Problem
Users often know their goal, but not the first practical steps to start.
Solution
Used AI-assisted planning prompts to turn high-level goals into clear, actionable task sequences.
05
Media / Automation
RSS / Parsing Cloudflare Workers
Light News
Summarized news feed tuned for quick daily scanning
Problem
Most news experiences are noisy and time-consuming to parse every day.
Solution
Built a lightweight pipeline for collecting, filtering, and presenting clearer summaries.
Writing

How the work thinks
out loud.

Notes on AI in MSP ops — architecture, safety, and why summarizers never quite become technicians.

Jul 2026
How Caisey Works

Architecture, information flow, independent risk evaluation, and the human-in-the-loop principles that keep technicians in charge.

Jul 2026
The MSP Transformation that wasn’t

Lots of MSPs are “trying out” AI. Very few are seeing it handle work — because context, access, and tools are still missing.

Technical Skills

What I work with

Frontend
  • React / TypeScript
  • Alpine.js
  • Tailwind CSS
  • HTML / CSS
  • Astro / Next.js
Backend
  • Node.js
  • Python
  • REST APIs
  • SQLite / D1
  • Syncro / Graph API
Cloud
  • Cloudflare Workers
  • Durable Objects
  • D1 / R2 / KV
  • Clerk Auth
  • Azure / Firebase
Methods
  • LLM / Agent Systems
  • MSP Ops Tooling
  • Troubleshooting
  • Product Ownership
  • Support Operations
Contact

Let's build something useful.

Open to roles and collaborations where AI meets real operational load — consoles, agents, and the boring glue that makes them trustworthy.

Email: [email protected]
GitHub: neckbeardthepirate
LinkedIn: judah-helland