VP of Operations

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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 the role?
We are looking for a Head of Business Operations. This is an executive-level role that reports to the CEO and will work closely with our Board of Directors. In this role, you will ensure the Clearcover organization scales efficiently and effectively and continues to deliver extraordinary results against ambitious objectives. You will be accountable for building, implementing and managing tools and systems for strategic planning and operational excellence, and providing general management of important company functions. You’ll also help develop the company’s overall strategy, support fundraising efforts, and lead a variety of other projects.

What will you do?

  • Evaluate, (re)build and manage the strategic planning systems for the company (currently, OKRs and some proprietary tools)
  • Drive productivity and accountability within the organization through systematic goal-setting and achievement tracking… i.e. make sure we’re always raising the bar
  • Institute and manage tools, frameworks, and systems to ensure the right balance of speed and qualitative/quantitative rigor in team and individual decision-making
  • Directly manage key functional areas of the business
  • Help develop the overall strategy of the organization, pushing the company and your teammates to balance 10x thinking and operational pragmatism
  • Ensure alignment and proper communication across all functional areas
  • Lead and support a variety of strategic projects, including equity and debt fundraising, partnerships, M&A, and organizational design/development
  • Lead planning and execution of Board of Directors and other key stakeholder updates and meetings
  • Build, tear down, and rebuild operational systems as we rapidly scale the organization
  • Be a steward of our core values, building and maintaining processes to ensure we adhere to Clearcover’s Operating Principles

What do you need?

  • Experience scaling business operations and processes at a rapidly scaling, growth-stage startup company (e.g. a company that quickly grew from 10s to 100s of people)
  • Significant experience developing and applying systems for organization and management with growth-stage startup teams
  • The ability to challenge the status quo, map business goals to process design, and design/test new initiatives
  • Experience evaluating/developing company strategy and raising venture capital
  • Experience building and leading high-performance teams and teams of teams
  • A belief that “process” is primarily a tool to remove constraints, not create them
  • Direct communication skills; comfortable giving critical feedback and holding people accountable for results
  • Management tool and process enthusiast (e.g. you can easily name your top 3 management books/mentors and decision-making books/tools)
  • Significant startup-focused financial literacy, including a deep understanding of unit economics and other early-stage KPIs (e.g. you obsess over how we design, refine and improve output and key metrics)
  • A passion for learning and improvement

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)
  • 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 
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Location

33 W Monroe, Chicago, IL 60603

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