Job Description

Overview Senior Systems Administrator at WeTravel. This in-person role is based in our Chicago office in the Loop (20 N Wacker Dr). The IT team is small but mighty, and you’ll be the go-to person for day-to-day IT support as well as proactive improvements to our tools and systems. You’ll work with teams like People, Operations, and Engineering to ensure WeTravelers have a seamless tech experience and the tools they need to work securely, from anywhere. From Your Hiring Manager: Hi! I’m Ivan Tarapon, Director of Platform & Infrastructure here at WeTravel. We’re looking for a Systems Administrator who’s organized, curious, and not afraid to tackle challenges. If you’re a problem-solver who thrives in a semi-remote environment and enjoys automation and optimization, you might be a great fit. This role is based in Chicago and will be hands-on; you’ll have opportunities to own projects and implement your ideas. We value automation and continuous improvement. Responsibilities Provide daily hands-on IT support for our remote team, with a focus on Mac devices and core tools. Manage access, permissions, and user setups across Google Workspace, Slack, Kandji, 1Password, Jira, and Confluence. Partner with HR and Ops to ensure smooth onboarding/offboarding and operational workflows. Create and improve internal IT processes, identify automation opportunities, and own initiatives from idea to execution. Help us scale and stay secure as our team grows. Qualifications At least 5 years of experience in a similar position. Solid experience supporting Mac environments in business settings. Experience with Google Workspace, Slack, 1Password, Kandji (or similar MDM), and Atlassian products (Jira, Confluence). Enjoy helping non-technical colleagues solve technical problems with patience and clear communication. Organized and methodical approach to solving IT issues. Proactive mindset: you spot inefficiencies, suggest improvements, and love automating workflows (bonus if you script). Can work independently and thrive in a fully remote setup. Benefits Competitive salary Health benefits for US team members: 100% employer-covered HDHP medical, DHMO dental, and standard vision or a plan that fits you. Generous Time to Recharge policy — unlimited paid time off to rest and recharge. Amsterdam Program — visit Amsterdam HQ for 2-4 weeks each year, staying in WeTravel apartments. Work remotely for a maximum of 4 weeks per calendar year. Annual team off-site. Extensive paid family leave. Three paid volunteer days per year. Two-week cross-functional onboarding program. Cutting-edge equipment and tools to set you up for success and coverage for certain WFH equipment. Join an international, travel-loving team with a passion for adventure and innovation. Equal Opportunities WeTravel is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. We welcome applicants from all backgrounds, experiences, and perspectives. If you're excited about this opportunity and believe you're a good fit, we encourage you to apply and join us in transforming the travel industry! #J-18808-Ljbffr WeTravel

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