MacOS Tech Support On-Site, Saint Paul, Minnesota

We’re looking to grow our small but mighty support team with someone who’s just as comfortable troubleshooting install problems as they are explaining how Cross Over works, all without sounding like a robot. You’ll be helping users run Windows apps on macOS and Linux, primarily over email and occasionally over the phone. If you’re curious, tech‑savvy and genuinely enjoy helping people, we want to hear from you.

We’re only considering local candidates currently. If you’re not within commuting distance of our St. Paul, Minnesota office, we won’t provide relocation support.

• Respond to customer tickets with clarity, warmth, and technical accuracy
• Occasionally hop on calls to guide customers through complex issues
• Troubleshoot Cross Over installs and compatibility challenges
• Learn by doing: dig into Cross Over and Wine to better understand how they work
• Document your work in tickets, write bug reports and share fixes with the team
• Contribute to our knowledge base and user guides
• Work closely with users and developers to identify and report bugs
• Collaborate with your teammates, balancing your workload and sharing insights
• Stay curious and keep learning—this is a tech-heavy role, and there's always more to know

• Experience in tech support or a customer-facing role
• Strong writing skills that are friendly, clear, and technically sound
• A willingness to ask questions and explore unfamiliar problems
• Comfort using macOS, Linux, and troubleshooting from the command line
• The ability to adapt when priorities change and tasks build up
• A team mindset with a willingness to share knowledge and ask for help
• A local address with the ability to work on‑site in St. Paul

• Familiarity with Windows or Linux
• Working knowledge of the command line
• Passion for Free and Open-Source Software

No lengthy online applications, repetitive questions or typing out your work history. We don’t use an applicant tracking system or a CRM. We believe in real people connecting with real people. Send an email to  and include the position in the subject line, your resume, and any work samples you find relevant. Don’t be afraid to tell us a little about yourself in your email—consider that your cover letter.

We’re curious about the critical stuff, like why Star Trek obviously crushes Star Wars (unless you have a strong argument otherwise), which Pantone color is your soulmate, whether you pledge allegiance to cats, dogs, or the chaos of owning both, what game has devoured more of your life than REM sleep, or your definitive take on the one true pizza topping.

We’re not saying this will affect anything... but we’re also not not saying that.