Senior Systems Administrator
WeTravel👋 From Your Hiring Manager
Hi! I’m Ivan Tarapon, Director of Platform & Infrastructure here at WeTravel.
I joined WeTravel to help build a secure, reliable, and scalable IT environment as we grow. Our team’s mission is to empower every WeTravel employee with the tools and support they need to work efficiently, securely, and without friction — no matter where they are in the world.
We’re looking for an Systems Administrator to help us level up — someone who’s organized, curious, and not afraid to jump into a challenge.
If you’re a problem-solver who thrives in remote setups, enjoys helping others, and gets excited about automation and optimization, you might be just who we’re looking for.
This role is an in-person role in our new Chicago office, located in the Loop (20 N Wacker Dr).
How We Work
Our IT team is small but mighty, and plays a critical role in making sure WeTravelers have a seamless tech experience. You’ll be the go-to person for day-to-day support, but also take part in bigger-picture improvements and proactive initiatives.
You’ll be working closely with teams like People, Operations, and Engineering — not just reacting to issues, but actively improving how we manage our tools and systems. Our stack is modern and remote-friendly: think Google Workspace, Slack, Kandji, Atlassian, 1Password, and a Mac-only environment.
We're looking for someone who enjoys structure but doesn’t need hand-holding — you’ll have room to own projects and implement your own ideas. And yes, we really do like people who automate the boring stuff. 😉
You Should Apply If You…
You have at least 5 years experience working in a similar position.
Have solid experience supporting Mac environments in business settings.
Have worked with tools like Google Workspace (G Suite), Slack, 1Password, Kandji (or similar MDM), and Atlassian products (Jira, Confluence).
Enjoy helping non-technical colleagues solve technical problems — with patience and clear communication.
Are organized and take a methodical approach to solving IT issues.
Have a 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.
You Might Not Be the Right Fit If You…
Prefer a very structured, ticket-heavy IT environment with little room for flexibility.
Don’t feel confident managing Mac systems and Google Workspace environments.
Get overwhelmed by juggling multiple tools or shifting priorities.
Don’t enjoy helping others or explaining technical concepts to non-technical teammates.
On a Weekly Basis, You’ll Be…
Providing daily hands-on IT support for our remote team — especially around Mac devices and core tools
Managing access, permissions, and user setups across Google Workspace, Slack, Kandji, 1Password, Jira, and Confluence
Partnering with HR and Ops to ensure smooth onboarding/offboarding and operational workflows
Creating and improving internal IT processes, identifying automation opportunities, and owning initiatives from idea to execution
Helping us scale and stay secure as our team grows
Benefits
Competitive salary
Your health matters – US team members get 100% employer-covered HDHP medical, DHMO dental, and standard vision coverages or a choice of plans that suit your needs.
Generous "Time to Recharge" policy — enjoy unlimited paid time off to rest, recharge, and show up as your best self.
Amsterdam Program – visit us in Amsterdam (HQ) for 2-4 weeks every year, staying in one of our WeTravel apartments.
Work remotely for a maximum of 4 weeks per calendar year.
Annual team off-site (often somewhere sunny 🌊).
Extensive paid family leave.
Three paid volunteer days per year — take time to give back to causes you care about, on us.
2-week cross-functional onboarding program.
Cutting-edge equipment and tools to set you up for success. Coverage for certain work-from-home (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!