We’re hiring a sysadmin to work with us on the hosting platform at Paid Memberships Pro. This is a remote position for our fully remote team.

If you’re worried about the title of sysadmin vs. SRE vs. something else, you’re probably not a good fit for the role or our company. Titles and responsibilities are fluid around here. If instead that excites you, keep reading.

The Ideal Candidate

The ideal candidate here is an experienced sysadmin who has seen some things, handled gnarly cases, and broken and fixed complicated systems.

At the same time, the ideal candidate is not only open to new tools but actively using or experimenting with AI tools like Claude Code and Codex. When you read stories about AI deleting production databases, you don’t think, “Oh yeah, never do that.” Instead, you think, “How could you avoid doing that while still using AI tools?”

Honestly, that’s the first question in the interview, so come prepared:

The ideal candidate here doesn’t balk at digging into the code or dealing with non-standard setups. If bad code is causing throttling on the server, you’re going to look at the code and try to figure it out. Before you tag in a developer, if you have to at all, you’re going to get as far as you possibly can. Instead of pushing work off on others, you ask detailed questions and pull others in while staying responsible for the issue yourself.

The ideal candidate finds a way to keep track of our entire fleet, cares for them like a flock of children.

• You don’t just keep the fleet running, you keep it thriving through small improvements here and there as you see them.
• You notice the orphaned servers, figure out what they were for, and shut them down carefully.
• You come into work and discover that the team building the hosting platform totally changed how all of this stuff works, and instead of complaining you figure out how you can help to hold it all together as we move quickly and break things from time to time.

A Note on Being On-Call

This job will have no on-call rotation and no pager. We don’t want you to work odd hours. We definitely don’t want to wake you up to do work in the middle of the night.

We define emergency narrowly: the customer’s site is fully down or broken. Warnings, tickets, and routine requests wait for working hours. Even in cases where the site is offline, we are relatively relaxed about getting the site back online and we’re honest with our customers about this. We have a handful of folks on the team who can address server emergencies.

As our customer base grows and the need grows, we will hire and train more folks to do this.

The Logistics

• Full-time, fully remote, any time zone. Our team spans 5+ countries.
• 35-hour work weeks, minimum 25 paid days off per year.
• USD $45,000–$90,000 base, depending on experience and location, plus healthcare and technology stipends.
• Everything we build is open source, including our whole hosting model. You’d be keeping the infrastructure under it honest.

How to Apply

You can read the full Systems Administrator job brief for the specifics. When you’re ready, email jobs@paidmembershipspro.com with your CV and answers to two questions:

1. Tell us about a gnarly incident you debugged where the root cause lived in a different layer than the symptom.
2. Tell us something exciting about how you are using AI tools at work or on the side.

Specific stories beat polished cover letters. We read everything, and yes, we can tell when an AI wrote your application for you rather than with you. The irony of filtering for that in this particular job is not lost on us.