AI Systems and Automation Specialist

The short version

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.

What we are honestly offering

A trade, stated plainly. 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.

What the work actually is

Once you are up to speed, roughly:

• Keeping our automation running, and being the person who finds out first when something breaks. Right now we find out because somebody notices a report did not arrive — building the error reporting that fixes that is one of your first real projects.

• Diagnosing failures that do not announce themselves. Our PSA will happily return zero rows, or every row, without throwing an error. You will learn to distrust anything marked "successful."

• Building new automation from a prioritized list of things that currently eat someone's afternoon every week.

• Supporting our client portal and, later, the compliance and training product inside it. Our owner and Director of IT are launching that themselves — it comes to you around month six, once you have your footing.

• 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 — including you.

• Credential hygiene, tracking what we spend on AI, and keeping a clear record of what client data goes where.

What you need on day one

• Some MSP or IT service experience. You understand tickets, time entry, RMM and PSA data, and roughly how the business makes money. This is the context everything else sits on and it is slow to teach from scratch.

• The troubleshooting instinct. You read error messages properly, change one thing at a time, and check against reality instead of assuming. If you have ever found a bug everyone else had written off as "just how it is," lead with that story.

• Evidence you taught yourself something nobody asked you to. A PowerShell script, a spreadsheet that got out of hand, a Zapier flow, a home lab. We do not care what it was. We care that the impulse is there.

• Reliability with recurring work that has a deadline. Part of this job is a compliance publishing cycle that runs on someone else's schedule and cannot slip. If precise repetition drains you, this will wear badly.

• Willingness to be corrected a lot for six months, and to find that useful rather than annoying.

• Clear writing. Enough that someone can follow your documentation without asking you.

• The ability to work remote without supervision — and to say something early when you are stuck instead of going quiet.

• Trustworthiness. This role eventually holds administrative access across every client environment we manage.

Compensation and logistics

• $65,000 to $80,000 base, depending on your MSP depth and what you have already taught yourself.

• Formal performance reviews at month three and month six against the ramp deliverables above, then annually.

• Full-time, exempt, with our standard benefits package.

• Fully remote within the United States. We do need you US-based: this role eventually holds administrative access to systems containing our clients' patient data, and our insurance and client agreements require that access stays domestic. It is not about trust — it is about what we can defensibly tell a dental practice during an audit.

• No on-call rotation during your ramp. If we add one later, we will pay for it and discuss it with you first.