Director of Engineering

| Chicago
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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 a Director of Engineering at Clearcover?
As the
Director of Engineering you will oversee the engineering talent and technical strategy for multiple domains and technical areas focused on our core product and APIs . This is a new role for Clearcover as we continue to expand as a business and grow our engineering teams. This role will report directly to the VP of Engineering and have a direct impact on our business performance and the continued growth of our engineering teams and technologies. The Director of Engineering will partner with Product Directors, functional business leaders, the VP of Engineering to accomplish large business and technology objectives. This role will have direct reporting responsibility for 2-4 engineering teams. We are looking for a leader who is passionate about people and technology and who has a proven record of scaling engineering teams and systems. 

What will you do?

  • Mentor, coach and develop individual contributors and managers 
  • Foster a high performing engineering culture which attracts a diverse spectrum of top engineering talent 
  • Own the quality, scalability, security, and performance of applications, systems, and integrations in the Clearcover domain
  • Measure and improve team engagement and productivity 
  • Set the technical strategy and execution plan for the domain 
  • Represent Clearcover as a brand ambassador to the local technology community 
  • Partner with the Director of Product to enable business value creation, as well as the stability and scalability of our solutions.
  • Build measurable goals with your teams and direct reports and ensure they are meeting or exceeding those goals
  • Promote simplicity in solving complex problems across our products and teams as we scale.
  • Play a key role in people-related initiatives including recruiting, onboarding, performance reviews, training, career advancement, etc.

What do you have?

  • Bachelor’s degree in Computer Science or related field. MS preferred.
  • Proven experience in software design and development
  • Experience leading multiple high-performing engineering teams, preferably in the ecommerce industry
  • Experience developing and getting stakeholder and engineer buy-in to execute a long-term technical strategy 
  • Expertise establishing and managing both onshore and offshore teams
  • Several years' experience building backend API centric software solutions
  • Deep understanding of cloud computing principles and practices. 
  • Strong expertise with languages/ technologies such as Ruby Java, TypeScript, Kotlin, .NET, Scala, etc
  • A strong understanding of database technologies
  • Prove expertise in agile software development
  • A proven ability to develop engineering managers and to build and retain diverse engineering teams 
  • Strong communication skills with the ability to understand and explain technical issues to a non-technical audience
  • Ability to provide honest, direct and actionable feedback to the team and follow up with relevant coaching and guidance  
  • Experience in a fast paced, Agile, continuous integration environment 
  • Creativity, fearlessness and an unwavering commitment to putting the customer first

Nice to haves?

  • Experience with automated unit and integration testing of infrastructure code
  • Experience with container security
  • Experience in one or more languages such as Python, Go, Ruby, or JavaScript

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.

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Technology we use

  • Engineering
    • KotlinLanguages
    • PythonLanguages
    • RubyLanguages
    • ScalaLanguages
    • ReactLibraries
    • Ruby on RailsFrameworks
    • PostgreSQLDatabases
    • SnowflakeDatabases

Location

33 W Monroe, Chicago, IL 60603

An Insider's view of Clearcover

How does your team reward individual success?

We celebrate "wins" on Fridays with the entire company where we celebrate the success of the week with the rest of the organization, it is a fun and casual way to be recognized by peers. However, I also find a moment to individually recognize my team during our weekly touch bases for something specific that they accomplished.

Rosyln

Head of Agency Distribution

How do you empower your team to be more creative?

I manage a hybrid team of traditional "creatives" and business strategists. I work hard to foster a spirit of creativity by asking my teammates to consider a variety of ways to solve every problem we encounter. Then, I create opportunities for them to be creative in ways that align with their superpowers.

Ariana

VP of Brand & Creative

What makes someone successful on your team?

People who are successful on the Customer Experience team communicate with empathy, love solving problems for our customers, continually look for ways to work smarter, and thrive in the face of challenge.

Heidi

Head of Customer Experience

What are Clearcover Perks + Benefits

Clearcover Benefits Overview

Clearcover offers a comprehensive benefits package along with a number of perks in an effort to support our employees and their families. We work to align our perks with our core values and empower our employees to balance work and their personal lives.

Culture
Volunteer in local community
Intracompany committees
Daily sync
Open door policy
Team owned deliverables
Team based strategic planning
Pair programming
Open office floor plan
Diversity
Dedicated Diversity/Inclusion Staff
Unconscious bias training
Hiring Practices that Promote Diversity
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
Wellness Programs
Onsite Gym
Retirement & Stock Options Benefits
401(K)
401(K) Matching
Clearcover provides employees with a 401(k) contribution of 3% of an employee's annual gross pay.
Company Equity
Child Care & Parental Leave Benefits
Child Care Benefits
Dependent Care FSA allows you to put away pre-tax dollars towards daycare expenses for dependents under the age of 13.
Generous Parental Leave
Clearcover offers parental leave for new parents after birth or adoption of a child. Full-time employees that have been employed for six months are eligible for six weeks of paid Parental Leave.
Flexible Work Schedule
Clearcover has flexible start and end times based upon your position and your team.
Remote Work Program
Our remote work program includes work from home Full-time remote for specific positions, as well as work flexible remote work for most position.
Family Medical Leave
Employees who have been with the company for 12 months are eligible for 12 weeks of family medical leave. Other policies apply to those here less than 12 months.
Return-to-work program post parental leave
Vacation & Time Off Benefits
Unlimited Vacation Policy
Paid Volunteer Time
Paid Holidays
Paid Sick Days
Employees receive 5 paid sick days each year.
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
We send snack boxes monthly since we are virtual.
Home Office Stipend for Remote Employees
We offer a one-time $250 stipend to set up your work from home office. Use this for anything that will support your work from home arrangement.
Professional Development Benefits
Job Training & Conferences
Clearcover offers a stipend to each employee to invest as they choose in their own professional development.
Diversity Program
Lunch and learns
Cross functional training encouraged
Promote from within
Time allotted for learning
Online course subscriptions available
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