IT Administrator

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Who’s Clearcover? 

Clearcover is the smarter car insurance company. We use powerful technology to offer everyday drivers better coverage for less money. We’re proud to be one of the fastest growing startups in Chicago, and we’re currently looking to add a few more extraordinary people to our team.

What is an IT Administrator?

We are growing fast and need help administering the software and hardware systems our employees use to do their jobs.  Our team is highly technical and can usually solve their own technical issues however sometimes they need help. Your desire and skills at finding solutions to issues quickly and efficiently are key to this role.  Clearcover is a SaaS first company -- virtually all the systems we use are cloud based.  

While cloud based systems solve a lot of problems, we still need to provision and configure them, they need to be monitored for issues and when things go wrong they need to be fixed or support needs to be engaged.  That’s where you come in.  Most of our users are on Mac’s and we have a modern mobile device management (MDM) system to monitor and provision them which makes this part of the job a joy.  

A few of our users are on Windows and you will be responsible for supporting them too.  Of course, computers break and employees need upgraded computers, you’ll be responsible for helping people get back up and running quickly when they do have an issue.  Finally, even before everyone went fully remote, we were heavy users of web conferencing systems.  As we eventually transition back to the office, we have a number of A/V which you will help support.

What will you do?

  • Manage, respond to and resolve technical issues and requests from local and remote employees.
  • Provision users, grant access, configure and monitor SaaS applications.
  • Set up new hires with equipment and appropriate access to the company’s system.
  • Evaluate and procure computer hardware, software and accessories.
  • Maintain, upgrade and enhance the company’s web conferencing and audio visual systems.
  • Monitor, audit and troubleshoot systems to ensure correct operation and to detect and correct anomalies. 
  • Document activities and develop “run books” for standard operational procedures.
  • Create reports for senior management.

What do you need?

  • You are highly organized and detail oriented. You’re able to manage priorities effectively and keep processes up to date.
  • You’re a great communicator. You’re able to understand complex technical issues and effectively communicate solutions both verbally and in writing.
  • You’re hands-on and a self-starter. You have the ability to identify important tasks and work with little oversight and direction.
  • You’re flexible. You have the ability to work amidst ambiguity and adapt as we grow and expand.
  • You have a growth mindset. You’re driven to improve performance through continued learning.

Nice to haves?

  • Experience administering GSuite.
  • Experience using and supporting Apple Mac devices.
  • Exposure to mobile device management systems (MDMs).
  • Experience with scripting with Bash or Python and administrative APIs

What's in it for you?

  • Unlimited PTO, we hire adults
  • Equity for all employees, so you own a piece of the pie too
  • Dental and Vision, we've got you covered 100%
  • Medical, we cover the vast majority of your premiums to make the cost of you and your family's coverage affordable. Plus, we contribute to your HSA and HRA (cha-ching)
  • We invest in your future by contributing 3% of your salary to a 401(K), even if you don't
  • Come to work pre-taxed through our FSA commuter benefits
  • and yes, we have unlimited LaCroix, beer, snacks and the occasional ice cream social (for once we’re back in the office) 

Clearcover is an Equal Opportunity Employer (EOE) that welcomes and encourages all applicants to apply regardless of age, race, color, religion, sex, sexual orientation, gender identify and/or expression, national origin, disability, veteran status, marital or parental status, ancestry, citizenship status, pregnancy or other reasons prohibited by law.


More Information on Clearcover
Clearcover operates in the Fintech industry. The company is located in Chicago, IL. Clearcover was founded in 2016. It has 570 total employees. It offers perks and benefits such as Volunteer in local community, Open door policy, OKR operational model, Team based strategic planning, Pair programming and Open office floor plan. To see all 3 open jobs at Clearcover, click here.
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