AI Systems and Automation Specialist

Darkhorse Tech

3d•$65,000 - $80,000•Remote

About The Position

We are a managed IT and compliance provider for dental practices. Over the last two years our owner and our Director of IT built an unusual amount of automation — roughly 35 production workflows, two AI voice agents that answer client calls after hours, internal apps our staff use daily, and a client portal that is about to launch. Neither of them is a software engineer. They built it with a troubleshooting mindset, AI coding assistants, stubbornness, and a deep understanding of how our business works. We are looking for someone with an MSP background and the same instincts, and the two of them are going to teach you to run it. If you are a service desk technician who has hit the ceiling of what tickets can teach you, and you have been quietly automating bits of your own job because the manual version annoyed you, this is written for you. We are paying what an experienced technician earns rather than what a fully-formed automation engineer costs, because you will not be one on day one. In exchange you get direct training from the two people who built all of this, and six months of protected ramp to become one. You will be trained, not thrown in. The first three months you are learning and documenting, not carrying a pager. Scope arrives in stages and we have written down what you own when. You will finish your first year with skills that were not on your resume when you started — API work, workflow automation, enough TypeScript to be useful, and the judgment to run a platform. Those are portable whether you stay or not, and we would rather be honest that they are yours. Formal reviews at month three and month six, against written deliverables rather than impressions. You will always know where you stand. You will be the only person doing this work, which means real ownership rather than a slice of someone else's project. The people training you are the owner and the Director of IT. Not a manager relaying instructions — the people who actually wrote it. The honest counterpart: the systems you inherit are load-bearing and largely undocumented, and a good part of your first few months is sorting out that mess. Some people find that satisfying and some find it grim. Worth knowing which you are.

Requirements

Some MSP or IT service experience. Understanding of tickets, time entry, RMM and PSA data, and roughly how the business makes money.
The troubleshooting instinct. Ability to read error messages properly, change one thing at a time, and check against reality instead of assuming.
Evidence of self-taught skills, such as a PowerShell script, a complex spreadsheet, a Zapier flow, or a home lab.
Reliability with recurring work that has a deadline.
Willingness to be corrected a lot for six months and to find that useful rather than annoying.
Clear writing skills, sufficient for documentation that can be followed without further questions.
Ability to work remote without supervision and to communicate proactively when stuck.
Trustworthiness, as the role eventually holds administrative access across every client environment.

Nice To Haves

API work
Workflow automation
TypeScript
Judgment to run a platform

Responsibilities

Keeping our automation running, and being the person who finds out first when something breaks.
Building the error reporting that fixes the issue of finding out about broken automation because somebody notices a report did not arrive.
Diagnosing failures that do not announce themselves, such as PSA returning zero rows or every row without throwing an error.
Building new automation from a prioritized list of tasks that currently consume significant time.
Supporting our client portal and, later, the compliance and training product inside it.
Looking after a growing set of small internal tools that our staff use daily and nobody currently owns.
Writing down how all of it works, so that none of it depends on one person again.
Credential hygiene, tracking what we spend on AI, and keeping a clear record of what client data goes where.