itsross
Big-company tech · One architect, no machine

The systems your business runs on. Built to hold up.

A decade in the engine room — identity, cloud, endpoints, migrations, the plumbing that takes a company down at 2 a.m. I find what's actually breaking and fix it at the root: sometimes that's AI, mostly it's the unglamorous infrastructure nobody else wants to own. The best version of hiring me is needing me less.

no reps, no runaround
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10 years in the engine room
A national health-tech company, an enterprise EUC/virtualization partner, and a national e-commerce brand.
What I go deep on
On-prem to cloud · identity & access · security · endpoints · AI automation. 3,000 endpoints migrated, 50+ servers.
~$420K/yr
in licensing, automated away — one script, 5,000 licenses retired.
Team of 8
led across identity, cloud & security — then chose to go back to building.
The build-up

It stacks up quietly. Then one day you can fix anything.

No titles, no logos — just the layers that became second nature, roughly in the order they did.

the fundamentals
endpoint fleets
identity & access
virtualization / EUC
systems that don't fall over
multi-cloud
leading the room
production AI

Old-school internet kid underneath it all — BASIC in the AOL era, scripting mIRC for fun. That hacker-curiosity never left; it just picked up a decade of enterprise on the way.

Your systems. Your infrastructure. Your uptime. It's Ross.

Same hands from the first message to the thing running in production — no handoffs, no re-explaining, no losing the thread halfway through.

"You're not hiring a vendor. You're getting the person who actually builds it."

Steve Ross
Steve Ross
hello@itsross.com
shameless plug → chatly.today
The rare part

Both, from one person.

Running enterprise infrastructure at scale and shipping AI into production almost never live in the same person. I've spent a decade on the first; the second I build for a living. That overlap is the whole point — someone who won't gamble your uptime chasing a demo, and won't hand you a fragile toy and vanish.

A decade of

Identity, cloud, endpoints, resilience — the plumbing that keeps a business standing when it's 1 a.m. and something's on fire.

And now

Production AI built on top of all that — so it survives real load instead of dying the moment it leaves the demo.

The work

I don't do tickets. I find what's actually broken, build the thing that fixes it for good — then I'm gone, and so's the problem.

I'm not staff, and I'm not a retainer you forget you're paying. The best outcome of hiring me is needing me less.

The bench it comes from —
01

Infrastructure & resilience

The systems that don't fall over. High availability, DR, active-active, monitoring — fault tolerance treated as the job, not a checkbox you tick at the end.

02

Identity, access & endpoints

Okta, Entra, AD, SSO/MFA, zero-trust — and the fleets underneath. Who gets in, what runs on their machines, and what breaks if it's wrong.

03

Cloud & migrations

On-prem to AWS, Azure, GCP — and the migrations to get there without taking you down. Old-school roots, so I actually know what I'm modernizing.

04

Production AI

Agentic, multi-model pipelines — and the unglamorous plumbing that makes them survive real load: context, evals, tool-use. The 90% nobody wants to build, which is the only part that matters.

05 · Automation & cost

I wrote a backup automation that retired 5,000 enterprise licenses — ~$420K/year, gone.

Who I help

Two kinds of people. Same wall.

If you're reading this, something's already working — and it's about to buckle under its own weight. That's usually right when people find me.

Small & mid-sized business

Growing faster than your systems can handle.

1 to 250 people, scrappy, ready to punch above your weight. You'll operate like the Fortune 500 — without standing up the Fortune 500 machine.

Builders & vibe coders

You built something real, fast. Now it has to hold up.

The tools got good fast — the boring half didn't come in the box. Auth, security, scale, the stuff that bites at 2 a.m. That gap isn't a you problem. I speak plain English and I'll tell you what's solid, what's a time bomb, and what to fix first.

Either way, the math is the same: if you're looking, you probably can't scale and you needed this yesterday. I'm not for people shopping the cheapest help desk — I'm for people who'd rather have one sharp person who actually gets it.

The receipts
Case · automation & cost
The problem

An enterprise was paying for ~5,000 archive licenses it barely touched — a line item everyone had stopped questioning.

The move

I wrote a backup automation that made those licenses redundant — same protection, none of the per-seat cost.

The result

~$420K/year, gone — recurring, from one script that keeps paying.

And the rest of the track record —
~$420K
/yr license costs eliminated — one backup automation retired 5,000 enterprise archive licenses.
3,000
endpoints migrated off on-prem AD → Entra ID, then off Omnissa → Intune.
Team of 8
led across identity, endpoints, networks, systems.
10 yrs
in the engine room: health-tech · enterprise EUC/virtualization · national e-commerce.
3 SaaS
products shipped solo — infrastructure to UI.

Skool365

End to end · solo

AI video-coaching for sports teams. AWS serverless (30+ Lambdas, API Gateway, DynamoDB single-table, S3 + MediaConvert pipeline, CloudFront), Amazon Bedrock (Claude summaries, Nova technique analysis), React web (coach + athlete portals) + React Native, Stripe, multi-tenant RBAC, COPPA-compliant, full CI/CD.

Chatly

Live on this page

Live AI chat-widget SaaS. One-line embed, self-training knowledge base, in-chat lead capture, one inbox, paid tiers. It's the bubble in the corner of this page. You're using my product right now.

See the feature page →

Landly

Same shop

Landing-page builder. Same shop, same hands, same standard.

Three products, shipped solo — infrastructure to UI. The same discipline that keeps enterprise systems alive, turned on my own.

Most small businesses run on duct tape and hope. "Capable" isn't "resilient" — half the "enterprise" gear I've seen is one bad sensor from a three-day outage. Boring, proven tech ships. If a pitch needs three buzzwords to make sense, it probably doesn't. I build transparent tech that just works — so you're not paying me to fight fires I started. One accountable person beats a faceless team and a ticketing system every time.

"I'll give it to you straight — what's solid, what's a time bomb, and what it's quietly costing you. Plain English, no runaround. If that's the kind of partner you want, we'll get along."

Don't sit in a queue waiting on a callback. Start a conversation right now — ask anything, tell me what's going on, or book time if you want it. You're basically already talking to me.