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Technical Analyst

Chicago, IL
  • Expired: October 23, 2022. Applications are no longer accepted.
Who's Clearcover?

Clearcover is a venture-backed technology start-up disrupting the trillion-dollar legacy insurance market. We've focused on building products that create confident, happy customers - and we're flourishing. We believe in putting our people first, paying them well, and working together to solve tough problems. If you'd like a high-growth opportunity with an award-winning company, let's chat.

We are excited to announce that Clearcover is ranked #151 on this year's Inc. 5000 list, landing us in the Top 3% of the fastest-growing privately held companies in America!

What is a Technical Analyst at Clearcover?

With ambitious growth in mind, Clearcover needs motivated experts to own and drive the configuration and launch various innovative insurance products. This role necessitates execution excellence and continual process improvement that are essential to the core of our business.

What will you do?
  • Connect the needs of product, actuaries, and business strategists with our technology platform
  • Perfecting the process and technology to deliver equitable pricing and products tailored to a wide range of customers and regions
  • Execute end-to-end software development and deployment in an agile environment with contributions from multiple teams
  • Build a deep understanding of insurance products, risk, and pricing through hands-on work and guided mentorship
  • Contribute to our development roadmap for business tooling to enable faster iteration in our business strategy
  • Drive continuous process and technology improvements
  • Use and improve our automated acceptance, integration, and unit testing strategies for rapid, accurate product launches
  • Trace and triage configuration and pricing issues through our consumer-facing and internal pricing technologies.

What do you need?
  • Ability to express strong communication skills; spoken and written.
  • Ability to understand and explain technical issues to a non-technical audience.
  • Ability to show strong understanding of REST and how to test web services with tools like Postman.
  • 1+ year of experience debugging the behavior of complex systems across multiple applications using SQL, Datadog, and other monitoring tools.
  • 1+ year of experience in quality engineering, testing or software development
  • Ability to show functional understanding of cloud computing
  • Ability to show your commitment to enabling our business customers with creativeness and fearlessness.

Did you know that women and minorities are less likely to apply to a position if they don't match 100% of the job qualifications? Don't let that be the reason you miss out on this opportunity! We encourage you to apply anyway. Don't count yourself out!

But wait, there's more:

As a people-first company, your health and well-being is a priority at Clearcover. We offer comprehensive benefits for individuals and families :
  • Medical. We offer rich and affordable BCBS plans for you and your dependents. If you select the high deductible health plan, we offer an HRA and contribute to your HSA.
  • Dental and vision. We cover 100% of dental and vision premiums for you and your dependents.
  • Pre-tax benefits, disability, and life insurance.
  • 401(k). We contribute 3%, even if you contribute nothing.

We've also curated a stack of perks and benefits that stretch beyond the expected. Our people have access to:
  • Generous vacation, 12 paid holidays, and parental leave.
  • Equity in the company (plus an evergreen plan) and an annual bonus program.
  • Employee resource groups, live yoga, and mental health workshops.
  • Top of the line hardware, snack stipends, and meeting free "Focus Fridays".

We're a remote first company, having paved the way for flexible work locations and continue to offer this flexibility. If you are local or in town visiting, you also have the choice to work from our Chicago HQ office.
  • Remote employees are eligible to work from: AZ, CO, CT, FL, GA, IA, IL, IN, KS, MA, MI, MN, MO, NC, NJ, OK, SC, TN, TX, UT, VA, WI.

To top it all off, if Clearcover is available in your state, you could have access to an employee discount on auto-insurance! Excited to learn more? Complete the application below!

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 identity and/or expression, national origin, disability, veteran status, marital or parental status, ancestry, citizenship status, pregnancy or other reasons prohibited by law.



Chicago, IL
60701 USA



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