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Dev/Ops Engineer

| Chicago

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. 

Reporting to Matt Dressel, VP of Engineering, the Dev/Ops Engineer will work with the larger Engineering team to create infrastructure, monitoring, and automation for Clearcover’s growing family of applications and services. 

What will you do? 

  • Help establish reliability standards for our services, and create tools to monitor and alert on outages and anomalies.
  • Build infrastructure and application deployment pipelines for a microservice architecture.
  • Help us migrate our applications from Amazon ECS to Kubernetes.
  • Work with the engineering and product team to automate the maintenance and deployment of AWS resources. 
  • Balance infrastructure, operational, and security concerns.
  • Build tools to support  high-velocity, self-service, agile product teams.

What do you have? 

  • Strong communication and experience collaborating between many teams
  • Experience maintaining AWS production environments using infrastructure-as-code tools 
  • Experience using SRE techniques to establish patterns for reliability
  • Experience in analyzing and visualizing monitoring sources including logs and metrics
  • Experience  in a production Kubernetes environment 
  • Worked in a multi-environment deployment architecture (Staging, UAT, Production)
  • Experience with Terraform, Docker, ECS, PostgreSQL, CI/CD tools systems ( e.g. Gitlab, Jenkins, etc)

Nice to haves: 

  • Security expertise 
  • Experience with secret storage and management
  • Experience monitoring with Prometheus and Grafana 
  • Familiarity with .NET and the Azure platform

What's in it for you?

  • Unlimited vacation and flexible work schedule, 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, 75% of your dependents and contribute to your HSA and HRA (cha-ching)
  • While we don't match yet, our 401(K) is pretty slick 
  • Come to work pre-taxed through our FSA commuter benefits 
  • and yes, we have unlimited LaCroix, beer, snacks and the occasional ice cream social 
Read Full Job Description


33 W Monroe, Chicago, IL 60603

An Insider's view of Clearcover

What's something quirky about your company?

It’s surprising how much we all grow to love discussing insurance. Everyone is genuinely interested in how the industry works and sharing knowledge. I think we feel we owe it to our customers to understand how insurance works, so they don’t have to. We’ve likely all thought at one point, “Wow, I never thought I’d care about insurance this much.”


Senior Software Engineer

How do you collaborate with other teams in the company?

Whether I'm working with Product to promote a feature launch or partnering with our Customer Advocate team to communicate updates to customers, I get to collaborate across teams, leverage my skills & improve my expertise every day. Clearcover nurtures a collaborative environment and encourages thinking outside the box to deliver better experiences.


Director of Communications

What are Clearcover Perks + Benefits

Volunteer in local community
Intracompany committees
Daily stand up
Open door policy
Team owned deliverables
Team based strategic planning
Open office floor plan
Health Insurance & Wellness Benefits
Flexible Spending Account (FSA)
Disability Insurance
Dental Benefits
Clearcover covers 100% of the employee's dental benefits.
Vision Benefits
Clearcover covers 100% of the employee's vision benefits.
Health Insurance Benefits
Clearcover's health insurance plan is with United Healthcare with a range of plans including PPO, HDHP and HSA. If you elect an HSA, we cover your out-of-pocket deductible as an HSA contribution.
Life Insurance
Clearcover offers voluntary life insurance.
Pet Insurance
Onsite Gym
Retirement & Stock Options Benefits
Company Equity
Child Care & Parental Leave Benefits
Generous Parental Leave
Clearcover offers parental and maternal leave with up to three months of paid time off.
Flexible Work Schedule
Remote Work Program
Family Medical Leave
Return-to-work program post parental leave
Company sponsored family events
Acme co. sponsors family oriented events Semi-annually.
Vacation & Time Off Benefits
Unlimited Vacation Policy
Generous PTO
Paid Volunteer Time
Paid Holidays
Paid Sick Days
Perks & Discounts
Casual Dress
Commuter Benefits
Clearcover's offers Commuter Benefits, employees can save an average of 30 percent off their commute by contributing pre-tax dollars.
Company Outings
Clearcover celebrates company wins by organizing quarterly outings to a variety of places like the Escape Room, Punchbowl Social and Bounce.
Game Room
Clearcover's game room includes a state-of-the-art ping pong table, custom Nerf gun wall and a Pop-a-Shot to let employees enjoy breaks between work.
Stocked Kitchen
Some Meals Provided
Professional Development Benefits
Job Training & Conferences
Clearcover offers a stipend to each employee to invest as they choose in their own professional development.
Lunch and learns
Cross functional training encouraged
Promote from within
Time allotted for learning
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