Head of People

Clearcover is looking for a Head of People to drive HR strategy and execution at one of the fastest growing companies in Chicago. We’re building a smarter choice for car insurance and want you to join us on this mission. 

To succeed in this role, you must believe in the power of shared core values, then build tools and process to ensure they are integrated with everything we do. You should also be able to handle tough issues with flexibility, agility and a willingness to let “some fires burn” – we’re looking for someone who can balance speed and structure.

As our Head of People and Talent, you’ll work hand-in-hand with the CEO to develop and execute the company’s strategies around headcount planning, recruiting, interviewing and hiring, onboarding, compensation, performance management, feedback and coaching, and employee relations and engagement. You’ll also work with other executives and our board of directors on organizational design.

Desired Skills/Experience
•5-7 years of human resources or people operations experience
•Direct experience at a rapidly-scaling technology startup (e.g. your company grew headcount 3-5x in 12-18 months)
•High empathy/EQ coupled with the ability to challenge directly and have difficult conversations
•Demonstrated experience developing and dismantling policies and procedures
•Demonstrated experience implementing employee programs including compensation (cash and equity), benefits, rewards, and training
•Impeccable and tactful communication skills
•Ability to think about problems from first principles, challenge assumptions and create new paths
•Ability to be analytical and make data-driven decisions, even in traditionally qualitative areas (e.g. evaluating core value “performance”)
•Studied familiarity with the HR/People strategies of other large, successful tech companies (Netflix, Google, Amazon, etc.)
•Experience developing or implementing a recruitment and onboarding program
•Strong background in managing and resolving employee relations issues
•Experience implementing HRIS/ATS systems and HR-focused KPIs/metrics

If you were the Head of People and Talent at Clearcover for the past month, you would have: 
•Worked on strategies to enhance our abilities to find shared core values and “superpowers” during the recruiting and interview process.
•Read (or reread) “How Google Works” and the Netflix “Culture Deck”
•Worked together with other divisional leaders to develop a hiring roadmap for the next quarter
•Challenged most of the assumptions behind our current HR practices… and perhaps some of your own assumptions too
•Learned a lot about insurance (for better or for worse…)
•Met with other members of our team to gather feedback on their professional and personal development goals
•Participated in our weekly Monday Commitments and Friday Wins sessions
•Learned what the “Over the Top” award is (and maybe even have won it)

About Us 
Clearcover, a Chicago-based company, provides high-quality car insurance at lower prices than traditional insurance carriers by applying advanced technology, avoiding unnecessary expenses and passing along the cost savings to customers. Clearcover has been featured in Forbes, Inc. and Venturebeat, for our innovative approach to changing the car insurance experience.

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