We’re hiring a Senior Engineering Manager in Chicago, IL

The engineering team at Root strives to be one of the most transformative engineering teams ever. We’re changing the way an industry works by leveraging technology and data to build the best products possible. Even with our significant growth, we operate in small teams that are given ownership over projects and results. We’ve found that the people closest to the problems are the best at solving them.

Our team excels at delivering software to solve the problems in front of us at Root: presently, a suite of world-class mobile, web, and server-based products obsessed with the customer experience. We’ve shaped our team and process around this; we know that constant iteration and experimentation produce the best results.

We recently raised one of the largest VC rounds ever for an Ohio technology company:  


For more information on engineering at Root see https://eng.joinroot.com/

We are looking for a Senior Engineering Manager to come and join our team. In this role, you will have responsibility for multiple product engineering teams across a vertical within our business.  Our technical leaders are expected to be hands on in the technical decision making process - although you won’t be writing code on a daily basis, we fully expect our engineering leaders to be able to read and write code, and more importantly both make and contribute to technical architecture decisions. You will own the technical architecture and roadmap decisions for an emerging product line built atop our existing business, so this leader will need to be skilled at looking around corners and anticipating “where the puck is going”. To support our long-term rapid growth, you will need to be exceptional at hiring and growing top-tier engineering talent, and not afraid to think outside of the box in order to do so. You will also be expected to manage at multiple levels and know when to dive deep and when to manage using auditing mechanisms. This includes helping to define KPIs, drive and improve operational posture, and be able to identify potential risks before they become issues.    

The Role & Responsibilities

  • Lead multiple engineering teams in having a transformative impact, redefining an industry that has underutilized technology and been stagnant for far too long.
  • Fluidly lead the transitions necessary to grow the engineering organization from 12 to 30+ engineers over the next 24 months.
  • Deliver working software to realize the tremendous advantage that Root has being an insurance carrier built on modern technology.
  • Maintain the momentum of a high-performing team that has excelled in building the entirety of a software platform necessary to run an auto insurance carrier.
  • Coach and grow new engineering leadership, especially cultivating new management talent within your scope
  • Continue to attract talent of the caliber that will make Root nearly unrivaled in its achievements relative to its team size.
  • Cultivate skills and manage performance, guiding your engineering organization in career progression, promotions, performance improvement, and hiring practices.
  • Collaborate fluidly with internal peers (Product, Design, Data Science, and more) on applying engineering expertise to deliver on organizational objectives.
  • Use your judgement and technical ability to follow problems wherever they lead as you work across departments to solve ambiguous, gnarly problems.
  • Professionally represent Root in conversations with clients and vendors as necessary.

Preferred Professional Qualifications

  • Proven ability and success running and scaling a team of developers, attracting outstanding talent, and creating a culture of innovation and technical excellence.
  • 5+ years of engineering leadership experience in a high-growth company, reliably executing on product roadmaps.
  • Ability to recruit and motivate top engineering talent. Can effectively manage teams ranging in size from 10 to 45 engineers.
  • Demonstrated technical leadership with significant exposure to growing organizations, enabling process, and growing software engineering teams (career mentoring, retention, advancement).
  • Familiarity with building large-scale products powered by backend API platforms and client-server architectures.
  • Strong technical knowledge, with the ability to understand critical path challenges and product delivery implications.
  • Experience with modern technology and the latest open source distributed systems and architecture knowledge is ideal.
  • Skilled at implementing and optimizing software engineering and product development methodologies and processes.
  • Strong communicator and past success working cross-functionally in partnerships with adjacent business functions in an evolving company.
  • Real strength around process management and implementation.
  • Eloquent and savvy leader who can find optimal execution for goals and objectives held by all stakeholders: founders, investors, and employees.

Personal Characteristics

  • Highly effective at creating collaborative relationships across an entire organization.
  • Comfortable in both scrappy and entrepreneurial environments as well as more sophisticated and later stage organizations.
  • A strategic thinker, with a vision that far transcends what is visible today.
  • Inventive, understanding when to pursue creative solutions to problems while being thoughtful of their trade-offs
  • An entrepreneur who sees ambiguity as opportunity, and obstacles as chances to build.
  • High energy and action-oriented with a history of getting things done in complex environments.
  • Integrity beyond reproach and the ethical soundness of a true leader.
  • Superior analytical skills and attention to detail with good business judgment and exceptional maturity, diplomacy, and communication skills (both written and verbal).
  • Results orientation with a strong work ethic. Must be tenacious, with the emotional intelligence to know when to push harder and when to look for alternative approaches.

Get in touch

Finding the right people to help us build Root is a top priority. Whether you would like to explore the possibility of working together or simply learn more about the position, we’d love to hear from you!

Apply now

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If you’d like to be a part of what we are building but don’t see an opening that suits you, email us at jobs@joinroot.com.