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Root

Engineering Director

Sorry, this job was removed at 02:05 p.m. (CST) on Tuesday, Mar 17, 2026
Remote
Hiring Remotely in United States
Remote
Hiring Remotely in United States

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Root is on a mission to unbreak insurance by creating experiences people love at prices they can’t believe. We believe that investing in world-class technology will facilitate a new class of insurance products, driving a massive positive impact on the hundreds of millions of drivers who carry auto insurance in the US. Root’s Engineering team is committed to building a flexible platform on which our product designers and quantitative scientists can quickly test ideas, deploy them into production, and iterate, with the ultimate objective of a delightful customer experience coupled with effective risk management.


The Opportunity


As we scale, we need a leader who can bridge the gap between complex insurance operations and world-class engineering execution. You will lead a multi-disciplinary organization of Engineering Managers across multiple product teams. Your success is defined by the health of your leadership pipeline, the clarity of your technical roadmap, and your ability to turn high-level business goals into scalable reality.


Salary Range: $225,000-$265,000 (Also eligible for competitive bonus and equity offering)
Root is a “work where it works best” company. This means we will support you working in whatever location that works best for you across the US.


While this role is remote-friendly, candidates must be located in the U.S. and some travel for interviews or meetings may be required.


How You Will Make an Impact

  • Partner with Product, Data Science, Analytics, Security, and experts in the Insurance Operations group to set the strategy for the quarters to come.
  • Establish and evolve a talent strategy that attracts, develops, and retains top-tier engineering talent at all levels.
  • Continuously evaluate the performance and effectiveness of your teams’ process in order to improve things over time.
  • Work closely with senior leaders in Engineering to improve the effectiveness of the Engineering organization as a whole.
  • Develop and ensure execution of technical strategy for your teams and Engineering as a whole to solve clear problems for the business.
  • Foster an environment of high accountability and psychological safety.
  • You look for high leverage actions and activities to drive meaningful improvements to the team, system, and process.


What You Will Need to Succeed

  • 7+ years as a people manager on software teams.
  • 12+ years in software engineering as a manager and individual contributor.
  • Proven leadership of strategic initiatives involving multiple teams across functional domains.
  • Excellent communication skills both with cross-functional colleagues and senior business leaders.


As part of Root's interview process, we kindly ask that all candidates be on camera for virtual interviews. This helps us create a more personal and engaging experience for both you and our interviewers. Being on camera is a standard requirement for our process and part of how we assess fit and communication style, so we do require it to move forward with any applicant's candidacy. If you have any concerns, feel free to let us know once you are contacted. We’re happy to talk it through.


Please see our Privacy Notice available HERE for more information on how we process your personal data.

Root Chicago, Illinois, USA Office

Chicago, IL, United States

What you need to know about the Chicago Tech Scene

With vibrant neighborhoods, great food and more affordable housing than either coast, Chicago might be the most liveable major tech hub. It is the birthplace of modern commodities and futures trading, a national hub for logistics and commerce, and home to the American Medical Association and the American Bar Association. This diverse blend of industry influences has helped Chicago emerge as a major player in verticals like fintech, biotechnology, legal tech, e-commerce and logistics technology. It’s also a major hiring center for tech companies on both coasts.

Key Facts About Chicago Tech

  • Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
  • Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
  • Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
  • Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
  • Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
  • Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory

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