IT Systems Administrator

New Contributor III

Company: When I Work

Department: IT

Location: Remote US/Canada (org is Minneapolis-based)



IT Systems Administrator managing zero-touch Apple device deployment and SaaS platforms at a cloud-centric, remote-first tech startup.

Job Description

As an IT Systems Administrator, your primary responsibility will be maintenance and management of When I Work’s cloud-centric internal IT infrastructure, ensuring that employees are able to work securely, effectively, and efficiently. You will report to the IT manager and work closely with your IT peers to respond to support requests, manage deployment processes, and continuously find opportunities for service improvements. You will manage a 100% MacOS fleet of devices across the US & Canada, operating in a zero-touch, zero-trust model.


In this role you will:

  • Work with your IT colleagues to design, implement and manage When I Work’s internal IT infrastructure.
  • Manage the acquisition, deployment and administration of our MacOS fleet.
  • Collaborate closely with our Finance team to manage our sprawling SaaS platforms, keeping an ongoing eye on spend and usage.
  • Help When I Work to continue succeeding as a remote-first company, with all the attendant new challenges and opportunities that come with this shift.
  • Maintain and expand our Apple DEP zero-touch device deployment model.
  • Improve the technology and employee experience backing our IT onboarding/deployment processes.
  • Help lead the rollout of the Okta Identity Provider platform for SSO & local MacOS login via Jamf Connect.
  • Document standard processes for intra-departmental and company-wide documentation and instruction.
  • Perform basic system administration, design, implementation, and maintenance tasks.
  • Contribute directly to the planning and execution of all IT processes at When I Work.
  • Mentor teammates on IT best practices.


Experience and Skills Needed

- Minimum of 5 years real-world Network/Systems Admin experience.
- Must demonstrate strong communication and interpersonal skills. - Ability to perform root cause analysis.
- Experience in engineering and administration of macOS systems.
- Strong knowledge of MDM protocol, configuration profiles, and policy management.
- Good working JAMF knowledge and experience.
- Experience deploying Apple hardware using DEP/ADE and MDM platforms (Jamf, Munki, SimpleMDM, Fleetsmith, etc.)
- Working knowledge of command line tools and common scripting languages (shell scripting, python)
- Experience creating configuration profiles and scripts for system deployment.
- Experience deploying and managing diverse SaaS platforms.
- Experience with Google Workspace (formerly G-Suite) products and management.
- Familiarity with configuring SAML SSO integrations.

What Would Be Awesome To Have

  • JAMF Pro product certifications and/or relevant experience (JAMF 200, 300, 400)
  • Knowledge/experience with general networking (VLANs, routing, traffic management, WiFi)
  • Experience managing Cisco Meraki networks (Security Gateways, Switches, Wireless APs)
  • VoIP phone system management experience, SaaS phone system knowledge a plus
  • Experience deploying and/or managing Okta, or equivalent SSO identity platform management.
  • Experience with developing onboarding/offboarding procedures using SSO provisioning APIs.

Company Description

Who We Are

We help hourly teams get shift done.

At When I Work, everything we do starts with a mission to help hourly teams work better together. We deliver on that mission by making every piece of hourly workforce management - scheduling, time tracking, shift trading, team messaging, and more - easy and straightforward for managers and employees alike.

The When I Work IT team is a small but experienced group with the targeted task of helping our colleagues succeed. We run a cutting-edge startup IT stack - Google G-Suite, Zoom, Slack, Atlassian, JAMF, Meraki, Okta, and Mac laptops. When you join this team, you will be joining a group of people who are resourceful, curious, dependable, and highly effective at getting Shift Done. You will have the unique opportunity to work independently coupled with the peace of mind that this close-knit team is always available for support.

Additional Information

What’s In It For You

  • Employee Stock Options
  • Professional development allowance
  • Paid parental leave
  • Medical benefits - employee premiums paid 100% by When I Work
  • Dental benefits
  • Paid vacation and holidays
  • Flexible work environment
  • 401K Match
  • Remote first culture including home office set-up stipend and ongoing telecommuter stipend
  • Casual dress code
  • Dynamic and dedicated team

We believe actions speak louder than words. Every encounter with our people and products should be memorable and helpful. Challenges are exciting, failure is how we learn, and we all have an entrepreneurial spirit. Building an inclusive and equitable workplace isn’t lip service. We invest our time and our money in organizations that are not only working to diversify the current jobscape, but also investing in the future of talent. We’re motivated by a strong, innovative, and passionate work culture and we’re constantly searching for ways to improve and get shift done.

How to Apply

Whether you’re a perfect match or not, if it sounds like a good fit, we encourage you to apply.

The tech industry is notorious for its lack of diverse representation, and we're aware of the research showing that historically underrepresented groups are less likely to apply to a job if they don't believe that they meet all of the criteria. Are you hesitant to submit an application because you're not sure if you check every box? Apply anyway! We would love to hear from you and figure out what you can add to the culture here at When I Work.

We’d love to talk to you! Please submit the following to apply:

  • Resume (including months/years of employment for each position).
  • Cover letter including:
  • an overview of your existing experience
  • a convincing reason why you’d like to work at When I Work.

*Must already be authorized to work in the United States on a full-time basis for any employer.