Head of IT

google g suite, cisco, python, bash, cyber security, nist, pci dss, software, hardware, director, leadership, cloud
Full Time
Depends on Experience
Work from home not available Travel not required

Job Description

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.

We are looking for someone to make our internal information technology systems awesome for our employees. We want to make sure we protect our customers, employees and companies information but make it easy for our employees to get their jobs done. When we bring new employees into the company, we want them to be delighted by the experience. When someone needs access to new systems or software, we want to make the process smooth and effortless for them. We want to provide networking that just works whether you in the office, at home or at the coffee shop. We are a cloud first organization and have technically savvy users that are creating a great company. We need information technology systems that supports this vision.

What will you do?

  • Oversee all technology operations, including network and device security.
  • Devising and establishing IT policies and systems to support the implementation of company objectives.
  • Evaluate and purchase efficient and cost effective equipment and software
  • Identify and recommend the need for spares, upgrades, configurations or new systems.
  • Assist and support departments in analyzing their technology requirements.
  • Prepare and control budgets and report on corporate IT expenditures.
  • Develop strategies to ensure the protection of our employee endpoint devices.
  • Manage licensing for subscription based services and provision/deprovision users.
  • Eliminate toilsome tasks through automation
  • Support AV systems and video web conferencing systems.
  • Respond to IT support requests from a technically savvy, and partially remote, team.

What do you have?

  • A cloud first mindset.
  • Roll up the sleeves and get stuff done attitude.
  • Proven experience in an IT leadership role in a growing company.
  • Sound understanding of computer systems (hardware/software), networks etc.
  • Scripting language experience with Bash and/or Python.
  • Experience with PCI DSS, SOC II and/or NIST Cybersecurity Framework.
  • Experience with asset and technology lifecycle management.
  • Experience in analysis, specification, implementation and evaluation of IT systems.
  • Excellent organizational, communication and leadership skills.
  • BSc/BA in computer science, engineering or relevant technical field.

Nice to have?

  • Experience managing Cisco Meraki networks (Security appliances, Switches, Wireless)
  • Experience managing Google G Suite applications
  • Experience deploying and managing Mobile Device Management solutions
  • Experience with Zoom video conferencing systems
  • Mac and Windows experience
  • 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 90% of your premium and 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

Posted By

33 W Monroe St Chicago, IL, 60603

Dice Id : 9110203sc
Position Id : 6146012
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