Yes — the reference is intentional. After twenty-plus years of senior IT consulting in regulated industries, it is also a fair description of the work.
For the part of the audience who hasn’t seen Pulp Fiction: in Tarantino’s film, Winston The Wolf is a fixer — a calm, well-dressed professional who arrives in the middle of a disaster, assesses what needs to happen, executes with precision, and leaves the situation measurably better than he found it. He does not panic. He does not improvise. He knows what he is doing because he has done it before.
That is also a fair description of the work I do. The clients we take on are usually not in a clean technology situation. There is a backup that nobody has tested. A practice management system that crashes mid-morning. A compliance audit coming in six weeks that the previous IT vendor was not equipped for. A multi-location operation where each office still acts like its own company on the network.
I happen to share the first name with the character. The disposition came independently. The combination is on-the-nose enough to acknowledge openly.
Twenty-plus years in IT, the entire career spent on the senior end of it. Trained in enterprise consulting at one of the Big Five firms — the kind of place where you learn how to walk into a room of Fortune 100 executives, listen carefully, ask the questions nobody else is asking, and propose a path forward that survives contact with reality.
Moved into direct Fortune 100 client engagements after that — the kind of work where technical decisions affect tens of thousands of employees and operational dollars in the eight and nine figures. Earned a Top Secret clearance and performed work in classified environments where downtime carried consequences beyond business revenue. MCSE certified, along with the rest of the alphabet that this work tends to accumulate, though the certifications were always less interesting than the engagements they enabled.
After two decades inside large firms and government-adjacent work, I founded Winston IT to bring the same discipline to mid-market businesses that don’t have a CIO of their own — the medical groups, dental practices, financial firms, manufacturers, law firms, and professional offices where the stakes are real but the in-house IT bench is thin.
The first thing I do on any engagement is audit. Network, identity, business systems, backups, security posture, compliance documentation, and the operational practices around all of it. I produce a written list of what is broken, what is risky, and what is fine — with priorities and rough costs. The client decides what to fix. We fix it.
The engineering discipline I bring is not unique to me — it is the standard at any senior consulting firm. Strict access controls. Defense-in-depth security architecture. Documented change management. Rigorous incident response. Network segmentation that assumes the perimeter has already been breached. What is unusual is bringing that discipline to a practice with twelve operatories, or a multi-office RIA with thirty-eight advisors, or a multi-plant manufacturer that has been bouncing between three different break-fix vendors.
That is the gap I close. The mismatch between what mid-market businesses actually need from IT and what most vendors at their price point are equipped to deliver.
Winston IT is not a one-person operation. We operate as a firm — senior engineers, dedicated leads per account, shift coverage for manufacturing clients whose lines run 24 hours. The standards I set are the standards every account experiences. Every engagement gets a named lead and a small dedicated team that stays for the life of the relationship.
No tier-1 ticket farm. No junior techs learning on your network. Same playbook across every site, every location, every engagement.
A meaningful portion of the work I am most proud of cannot be discussed publicly. The clients, facilities, and technical specifics are subject to disclosure restrictions I honor without exception. The engagements happened. The discipline they instilled informs every commercial engagement I take on today.
If you are inquiring from an organization that has standing to verify cleared work, you will know how to reach me through the correct path. If you are a commercial client, that history is still relevant — the engineering discipline that comes from cleared work is the same discipline I bring to commercial engagements, scaled appropriately. You pay commercial prices for the kind of rigor that, in a different setting, was the price of admission to keep working at all.
Offices in Chicago, San Diego, and Honolulu — three coasts, three time zones, on the ground in each. Most ongoing client work runs remotely; for installs, audits, incident response, and new-location buildouts, I and the team travel anywhere in the United States.
Bilingual English / Spanish support is part of how the firm operates — for front-desk staff at medical and dental practices, line workers in manufacturing, and clients across the country whose first language is Spanish.
If you fit one of these profiles, the conversation is worth having:
— You operate across multiple locations and IT feels like it is fighting you
— You are in a regulated industry and the next audit is keeping you up
— You have been through two or three IT vendors and none has stuck
— You are growing — new office, acquisition, new line of business — and the IT scaffolding is starting to crack
— Your current vendor handles tickets but cannot explain your IT strategy
— You need someone who understands compliance, security, networking, business systems, and AI — not five different specialists
20-minute scoping call. No sales pitch. I’ll tell you whether we’re a fit and, if we are, what we would do.
Email to book a scoping callOr use the form on the contact page.