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.

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 Type Script 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.

• 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.

• 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 Power Shell 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…