Senior Engineering Manager

| Chicago

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:  

https://techcrunch.com/2019/09/09/root-insurance-valuation-hits-3-65-billion-in-latest-round-led-by-dst-global-and-coatue/

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.
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Technology we use

  • Engineering
    • JavaLanguages
    • JavascriptLanguages
    • PythonLanguages
    • RLanguages
    • RubyLanguages
    • SqlLanguages
    • SwiftLanguages
    • ReactLibraries
    • ReduxLibraries
    • React NativeLibraries
    • Ruby on RailsFrameworks
    • PostgreSQLDatabases
    • RedisDatabases

An Insider's view of Root

What does your typical day look like?

A quick standup followed by opportunities for both pairing and soloing. Maybe an occasional design meeting or retrospective. My team sits at the intersection of a lot of technologies so the day-to-day work varies. There's time carved out to learn technologies that are new to me and to help lead others with the technologies that I already know well.

Jordan

Senior Software Engineer

How does the company support your career growth?

I think the emphasis on team rather than personal responsibility makes Root a great place to grow. Engineers aren't concerned with producing their "own" work at the exclusion of helping others. Engineers at Root also just love problem-solving and step up to whatever problems I come to them with.

Liz

Software Engineer

What are Root Perks + Benefits

Root Benefits Overview

Our benefits exist to support exceptional employees in doing their very best work. We have full health, vision, dental insurance and we cover 100% of the premiums for employees and 75% for dependants.

Culture
Eat lunch together
Daily stand up
Open door policy
Team owned deliverables
Team based strategic planning
Pair programming
Open office floor plan
Health Insurance & Wellness Benefits
Flexible Spending Account (FSA)
Root employees can contribute up to $2700 annually to their FSA.
Dental Benefits
Our dental plan covers $1250 of expenses.
Vision Benefits
The vision benefits plan covers 100% for annual eye exams with $130 for glasses and contact lenses.
Health Insurance Benefits
A health insurance plan that provides for you and your family.
Life Insurance
Employer-paid for life insurance is equal to 60% times an employee's annual salary.
Pet Insurance
Pet insurance that protects your four-legged loved ones.
Retirement & Stock Options Benefits
401(K) Matching
Root contributes the equivalent of 3% of your salary to your 401(K) regardless of your contribution.
Company Equity
Root offers incentive stock options that vest over a 4-year period for all of our Engineering roles.
Child Care & Parental Leave Benefits
Generous Parental Leave
We provide up to 12 weeks of parental leave for the primary caretaker. Root also provides 6 weeks of leave for the secondary caretaker.
Flexible Work Schedule
Root provides employees with a flexible work schedule but our core hours are generally 9-5.
Vacation & Time Off Benefits
Unlimited Vacation Policy
Paid Holidays
Paid Sick Days
Perks & Discounts
Casual Dress
Commuter Benefits
Root offers up to $100 a month for qualified commuter expenses.
Free Daily Meals
We provide catered lunch every day.
Stocked Kitchen
Root has a stocked kitchen of snacks and drinks. Everything you need to do your very best work.
Relocation Assistance
We offer competitive relocation packages.
Professional Development Benefits
Job Training & Conferences
Root has a continuing education budget for conferences, online resources, and certifications that are related to their work.
Lunch and learns
Root hosts weekly lunch and learns from
Cross functional training encouraged
Promote from within
Time allotted for learning
We have 12 hack days a year for engineers to explore new technologies or build things that aren't prioritized on our product roadmap but pique their interest.

Additional Perks + Benefits

Our carefully curated benefits and perks exist to empower our employees to do their very best work by bringing their authentic selves to work every day.

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