IT Monitoring Specialist

CONNECTING PEOPLE, CULTURES, AND STORIES

Founded in 2017, WeRoad is a fast-growing startup that is disrupting the travel industry in Italy, Spain, UK, Germany, France and Switzerland!

With 200 team members and 4K Travel Coordinators, we’re a community of travelers who turn every trip into a life-changing experience. We’re on a mission to design and deliver experiences worth living and sharing, through rewriting the rules of the travel industry.

Before you apply, please read through our Cultural Manifesto

JOB TITLE: IT Specialist

Hybrid (Milan)

TYPE OF CONTRACT: Full time

Administer Google Workspace end-to-end (users, groups, OUs, security, integrations) and own identity & access management through Jamf Connect and Google Credential Provider for Windows.

Manage our device fleet via JAMF Pro and NinjaOne enrollment, configuration profiles, patching, monitoring, and compliance.

Support WeRoaders on-site and remotely via remote control, and run onboarding/offboarding end-to-end, hardware, accounts, access, and clean deprovisioning.

Administer and roll out the company’s SaaS stack and AI tools, handle licenses and user access, enable colleagues through internal training, and keep their use secure and well-governed (data, policies, shadow IT).

Vendors & contracts: Manage hardware and software contracts, supplier relationships, licenses and renewals, keeping costs, SLAs, and vendor performance under control.

Continuously improve IT processes, documentation, and automations to keep up with the pace of a scaleup.

3+ years in an IT / Workplace / Systems role, ideally in a fast-moving scaleup or tech-driven environment.

Hands-on admin of Google Workspace, JAMF Pro, and NinjaOne, with a solid grasp of IAM, SSO, and basic security & compliance. Jamf Connect, Protect and GCPW are a strong plus.

A commercial streak: You’ve managed supplier relationships, IT contracts, SaaS licenses and renewals before, and you’re comfortable tracking costs and negotiating terms.

Clear communicator who enjoys helping colleagues and translating tech into plain language.

Languages: Fluent in both Italian and English; any additional language is a plus.

You want to be part of a young, smart, and fun team that shares your passion for travel. You make decisions quickly, test, learn, and adapt—because growth comes from action.

Our WeRoaders and Travel Coordinators are at the core of everything we do, and you’re eager to be part of something bigger.

Performance-based bonus – A discretionary annual variable bonus, and based on performance and company results.

A free WeRoad trip every year – Choose your dream destination with €1,400/year travel discount or travel even more as a Travel Coordinator.

Trust-based holidays – We believe performance is driven by impact, not by hours at a desk. Opportunities to learn – We invest in your growth with training and learning opportunities.

New parent support – €3,600/year for 3 years after birth or adoption (or prorated if your child is under 3 when you start at WeRoad).

Hybrid working - Flexible working, and we support you to work from your destination of choice up to 1 month per year.

At WeRoad, cultural fit matters as much as skills. With multiple steps, we make sure every new joiner is not just a match, but 150% aligned with our Culture.

introductory call with Talent Acquisition Lead

Statistically speaking, women are less likely to apply for roles where they don’t fit the job description perfectly.