Automation Engineer (Python) - US medical practice, long-term, $1,800-2,600/mo

We are a small physician-owned pain management practice in New York. We run our own document pipeline: providers fill in patient visit forms, Python and Node scripts turn them into clinical notes, and browser automation files them into our EMR. It runs nightly on a Mac and in Google Cloud.

It mostly works. When it doesn't, it usually fails silently - a job reports success and the output is empty. Your job is to own that pipeline and make it honest.

WHAT YOU WILL ACTUALLY DO

• Maintain a Python and Node.js codebase plus six scheduled jobs on macOS launchd and Google Cloud Scheduler
• Read the nightly audit output every morning and work the exceptions
• Write a failing test for a defect before you fix it
• Improve the monitoring so that a job which ran but did not work is visible without a human noticing
• Occasionally join a call with the doctor and explain what broke, in plain English

YOU MUST HAVE

• Real Python. Not "I have used Python" - you can debug code you have never seen before, written by someone else
• Comfort in a terminal: git, cron or launchd, log files, ssh
• Enough JavaScript to maintain a Playwright or Puppeteer browser automation script
• The habit of checking that a thing worked, rather than that it ran
• Reliable power and internet, and a machine you can work on for eight hours

NICE TO HAVE
Google Cloud (Functions, Scheduler, Storage). PDF form tooling. Any exposure to US healthcare.

HOURS AND PAY
40 hours a week, of which 4 must overlap 9am-1pm New York time. The rest you schedule yourself.
$1,800-$2,600 per month depending on what you demonstrate, paid twice monthly, plus 13th month pay in December. Reviewed at six months.
This is long-term. We are not looking for project work and we are not looking for an agency.

ABOUT THE DATA
This role handles US patient health information. You will be trained on HIPAA, you will sign a confidentiality agreement, and you will be given your own named logins. You will never be asked to share an account or to use someone else's.

HOW TO APPLY - read this part carefully, it is the first test.

Start your application with these two lines, exactly, each on its own line:

PIPELINE-2026
LEDGER

Then answer these three, numbered, in this order:

1. A link to code you have written that I can read - GitHub, GitLab, a gist, anything. If you cannot share code, instead describe in five sentences the hardest bug you have ever found in someone else's code, and how you found it.

2. A script runs every night, exits with status 0, and writes an empty file. There is nothing in the logs. Name the three things you would check first, in order.

3. If our workday starts at 9:00 AM in New York, what time is that where you are, today? Would your answer be the same in January? Explain in one sentence.

Applications that do not follow this format are not read. That is not a trick - it is the job. Following an instruction exactly, every time, is most of this work.