Job Brief: Systems Administrator
Stranger Studios, LLC is a creative firm that builds open source technology and produces digital content to help people get paid. All of our software is free to use. All of our content is free to consume.
Stranger Studios builds products around the platforms we create, including support, automation, guidance, and enhanced content delivery. Businesses that use our platforms benefit from fast, secure software built specifically to help them make more money. Individuals and organizations use that money to find freedom in their lives and to achieve their respective goals.
About the Systems Administrator Role
We are looking for a Systems Administrator to take ownership of our hosting platform, the infrastructure that keeps our customers' membership sites online and running smoothly.
This is a hands‑on role. We need someone who does the work themselves: patches the servers, reads the logs, writes the runbook, fixes the thing. You will collaborate closely with a small team and work in the open, but the day‑to‑day health of the platform is yours.
If you’re worried about the title of Systems Administrator versus SRE or something else, this is probably not the right role for you. Titles and responsibilities are fluid around here. If that excites you, keep reading.
Our setup is atypical on purpose. We host one site per server, with no shared servers and no lock‑in, automate aggressively, and lean heavily on AI tools to help us build, maintain, and document our infrastructure.
An AI agent works alongside our team with real access to the platform: it monitors the fleet, investigates issues, and proposes changes. Part of this job is being the experienced human in that loop: reviewing its work, improving the runbooks it executes, and supplying the judgment it doesn’t have.
The right candidate finds that genuinely exciting: open to non‑standard approaches, fluent enough with modern AI tools to use them as a force multiplier, and grounded enough in Linux fundamentals to know when to override what an AI suggests.
Stranger Studios is a great place to work.
- Fully remote team with diverse members in 5+ different countries.
- 35 hour work weeks.
- Flexible paid time off policy for full time team members, with a minimum of 25 paid days off per year.
- Competitive salaries.
- Stipends for healthcare and technology expenses.
- Join a team that cares about your growth and well‑being.
Responsibilities
As our Systems Administrator, you will own the day‑to‑day health of our hosting platform. Customers trust us to keep their sites online; you will be the person making sure we live up to that trust.
Responsibilities include:
- Manage the Fleet: Oversee a growing fleet of Ubuntu Linux servers on DigitalOcean, one customer site per server, running the LAMP stack (Linux, Apache, MySQL, PHP) and WordPress. This is fleet management, not server babysitting: golden images, repeatable provisioning, and fleet‑wide rollouts rather than hand‑tuning individual boxes. You keep track of the whole fleet, notice what doesn’t belong, and make careful improvements that keep it healthy over time.
- Maintenance and Updates: Keep our servers up to date with security patches, software updates, and best practices.
- Troubleshooting: Monitor, diagnose, and address traffic, performance, and security issues as they arise across the whole stack. When a site is broken in the browser but fine from the command line, you know to suspect the layers in between.
- Own the Weird Problems: Dig into code when needed and work effectively in non‑standard setups. If bad code is causing throttling on a server, you do not stop at "that’s a dev problem." You get as far as you can, ask good questions, and stay responsible for the issue while pulling in others as needed.
- Operational Stability: Be the calm, careful counterweight on a team that ships fast. Catch what we miss, push back when something needs more thought, and make sure routine maintenance and observability never get deferred.
- Documentation: Maintain runbooks, infrastructure decisions, and incident postmortems clearly enough that the next person, human or AI, can act on them.
- Work with our AI Tooling: Review changes proposed by our AI agent, improve the automation and runbooks it runs, and serve as the human judgment layer for the platform.
- Advise on Tooling: Partner with our development team on the design and rollout of internal tools, server templates, automation, and APIs that support the hosting platform. You will not be expected to lead software development, but your operational perspective should shape what gets built.
What you might have worked on last month
Real examples from our platform, lightly sanitized:
- Traced a fleet‑wide alert storm to a monitoring container that didn’t survive a host reboot, fixed the container restart policy, and wrote up the gotcha so it can’t surprise us twice.
- Debugged a customer site returning 500 errors after an automatic plugin update; the command line worked fine, the front end didn’t, and traced it to PHP opcache behavior under our configuration, then hardened the update pipeline so the whole class of problem went away.
- Reviewed and shipped a provisioning fix so newly created servers allow our monitoring hosts from first boot, instead of firing a false alarm three minutes after creation.
After‑hours expectations: the honest version
- There is no scheduled on‑call rotation and no pager.
- We do not want you working odd hours, and we definitely do not want to wake you up in the middle of the night to do routine work.
- We define "emergency" narrowly: a customer site fully down or broken. Warnings, tickets, and routine requests wait for working hours. Our service commitments are not built around uptime nines.
- Monitoring and AI tools handle first‑line detection and triage around the clock.
- We have a handful of people on the team who can address genuine server emergencies, and the rare true after‑hours issue is shared among several of us, including you.
- If after‑hours work ever becomes regular rather than rare, we treat that as a problem to fix, not a norm to absorb.
Skills and Qualifications
- Demonstrated experience managing production Linux servers, particularly Ubuntu. You have seen some things, handled gnarly incidents, and broken and fixed complicated systems.
- Strong proficiency with the LAMP stack (Linux, Apache, MySQL, PHP) in WordPress hosting environments, including comfort with wp‑cli.
- Cross‑layer debugging instincts. When a site 500s but the CLI works, you reach for opcache, PHP‑FPM, and cron state, not just the plugin list.
- Solid understanding of server security, performance tuning, monitoring, and incident response.
- Comfort at the command line and with shell scripting; comfort reading and modifying configuration management code (Ansible or similar).
- Willingness to dig into code and follow a problem across layers before handing it off. You do not push work away just because the root cause turns out to live somewhere unexpected.
- Methodical attention to detail. You read the docs, you check the logs, and you double‑check the irreversible commands.
- Clear written communication. You can write a runbook a teammate can actually follow, and you work in the open: async writeups and shared channels, not a silo.
- Real, current practice with AI tools (Claude, ChatGPT, or similar) as part of your daily work, and the confidence to push back when they’re wrong.
- Comfort with non‑standard approaches. We have made deliberate choices that diverge from common WordPress hosting patterns, and we want a colleague who can engage with the reasoning rather than insist on the textbook version.
Salary Range
This is a full‑time, fully remote position open to candidates in any timezone.
Annualized base salary ranges from USD $45,000 to $90,000, based on experience and location. Stipends for healthcare and technology expenses, and other benefits, are discussed alongside the base salary.
Bonus Skills and Qualifications
- Experience with DigitalOcean specifically (Droplets, Spaces, snapshots, monitoring).
- Hands‑on Cloudflare experience (DNS, WAF, page rules, Workers).
- Familiarity with Ansible and infrastructure‑as‑code workflows.
- Experience operating Prometheus / Grafana / Alertmanager observability stacks.
- Comfort with Docker and docker‑compose for operational tooling.
- Experience with Tailscale or similar mesh VPNs.
- Experience designing or operating WordPress hosting at scale.
- Familiarity with Restic, MySQL replication, Postfix, or similar adjacent tooling.
Core Values
At Stranger Studios, we believe in purposeful work, mutual respect, and commitment to open‑source principles. We embrace our humanity, balancing work with life and fostering an environment where team members and customers feel valued. We take ownership of our work, collaborate with empathy, and strive to build software that is both effective and free for others to use and learn from.
Joining our team means aligning with these values and contributing to a supportive, respectful, and innovative environment.