Root Insurance

Own and architect Jira platform strategy, lead migration efforts, and enable product discovery workflows, while influencing cross-functional teams. | Deep Jira expertise, experience leading platform migrations, and strong stakeholder management skills. | The Opportunity We are seeking a Lead Business Systems Engineer to provide strategic ownership and technical leadership of our Jira product suite, including Jira Software and Jira Product Discovery, as we migrate from Shortcut and Productboard. This role operates with a high degree of autonomy and influence, owning system architecture decisions, platform strategy, and long-term scalability for product development tooling. As a senior individual contributor, this role partners closely with Product, Engineering, Program Management, and Leadership to ensure Jira enables efficient product discovery, planning, execution, and insight across the organization. Salary Range: $108,000-$132,000 (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. How You Will Make an Impact Strategic Jira Platform Ownership Serve as the principal owner and architect for Jira Software and Jira Product Discovery. Define and evolve Jira platform strategy, architecture, and standards aligned with company growth. Design and maintain complex Jira configurations including workflows, issue hierarchies, custom fields, automations, permissions, and schemas. Evaluate and manage Atlassian Marketplace apps and integrations to extend Jira capabilities. Migration & Transformation Leadership Lead the end-to-end migration from Shortcut and Productboard to Jira Software and Jira Product Discovery. Drive discovery and decision-making on future-state workflows, data models, and governance. Partner with senior Product and Engineering leaders to align Jira design with operating models. Own migration planning, execution, risk management, and post-migration optimization. Jira Product Discovery Enablement Architect Jira Product Discovery to support scalable idea intake, discovery workflows, prioritization frameworks, and roadmapping. Ensure strong alignment and traceability between discovery, delivery, and outcomes. Enable executive-level visibility into product priorities and progress through Jira configurations and reporting. Cross-Functional Leadership & Influence Act as a trusted advisor to senior stakeholders on Jira capabilities, tradeoffs, and best practices. Translate ambiguous or evolving business needs into durable system designs. Influence teams toward standardized, scalable solutions while balancing flexibility. Mentor junior Business Systems Engineers and Jira administrators through design guidance and best practices. Governance, Risk & Optimization Establish and enforce governance models for Jira configuration changes, access, and data quality. Proactively identify and remediate system risks, performance issues, and configuration debt. Continuously evaluate platform usage and drive simplification and optimization initiatives. Ensure Jira remains secure, performant, and compliant with internal standards. What You Will Need to Succeed 7+ years of experience in Business Systems Engineering, Systems Administration, or a related field. Deep expertise administering and architecting Jira Software in large-scale, multi-team environments. Proven experience leading complex tooling migrations or platform transformations. Strong understanding of Agile, Scrum, Kanban, and modern product development practices. Demonstrated ability to operate independently and lead initiatives with broad organizational impact. Excellent stakeholder management, communication, and influence skills Nice to Have Hands-on experience with Jira Product Discovery. Experience designing product discovery and delivery ecosystems. Advanced experience with Jira automation, APIs, scripting, or integrations. Familiarity with the broader Atlassian ecosystem (Confluence, Jira Service Management). Experience in SaaS or high-growth technology organizations. 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. Consistent with the Americans with Disabilities Act (ADA) and the Civil Rights Act of 1964, it is the policy of Root to provide reasonable accommodation when requested by a qualified applicant or candidate with a disability, unless such accommodation would cause an undue hardship for Root. The policy regarding requests for reasonable accommodation applies to all aspects of the hiring process. If reasonable accommodation is needed, please contact recruiting@joinroot.com

Designing, building, and maintaining web applications and APIs, collaborating with teams, and optimizing performance. | Requires 4-7 years of experience in software engineering, strong backend skills in Ruby on Rails, experience with distributed systems, cloud infrastructure, and system reliability. | The Opportunity We’re looking for a Senior Software Engineer to join our Partner Activation Engineering team. In this role, you’ll design, build, and operate systems that enable seamless onboarding, integration, and activation of strategic partners. You’ll work closely with product, partnerships, and other engineering teams to deliver reliable, scalable solutions that directly impact company growth. As a Senior Software Engineer, you’ll take ownership of complex features and services, contribute to architectural discussions, and help raise the technical bar through strong engineering practices and mentorship. Salary Range: $133,784-$155,000 (Bonus and LTI Eligible) 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. How You Will Make an Impact Design, build, and maintain core services, APIs, and workflows Own features end-to-end, from technical design through production support Collaborate with Product, Partnerships, and Platform teams to translate business needs into well-architected technical solutions Contribute to system design discussions and help evolve service architecture over time Write high-quality, well-tested code and participate in thoughtful code reviews Help identify and reduce technical debt while balancing delivery and maintainability Mentor and support other engineers through pairing, code reviews, and knowledge sharing Participate in on-call rotations and contribute to operational excellence What You Will Need to Succeed 4–7 years of professional software engineering experience working on production systems Strong experience building backend services and APIs in Ruby on Rails Experience working with distributed systems and cloud infrastructure Comfort owning features and services with minimal oversight Solid understanding of data modeling, performance, and system reliability Strong communication skills and ability to collaborate across disciplines A pragmatic, product-minded approach to engineering Nice to Have Experience building partner-facing platforms or external integrations Familiarity with event-driven architectures and asynchronous processing Experience working in regulated or high-availability environments Prior experience mentoring junior engineers Understanding of API schemas, particularly OpenAPI/Swagger Tech Stack Backend: Ruby on Rails monorepo APIs & Integrations: RESTful APIs, webhook-based integrations, Kafka-based event streaming Cloud & Infrastructure: Docker, Terraform, AWS (ECS/EKS, EC2, RDS, S3, Redshift), Buildkite Observability: Datadog and Sentry for logging, metrics, and alerting Security: OAuth2, JWT-based authentication, role-based access control 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. Consistent with the Americans with Disabilities Act (ADA) and the Civil Rights Act of 1964, it is the policy of Root to provide reasonable accommodation when requested by a qualified applicant or candidate with a disability, unless such accommodation would cause an undue hardship for Root. The policy regarding requests for reasonable accommodation applies to all aspects of the hiring process. If reasonable accommodation is needed, please contact recruiting@joinroot.com

Lead and coordinate engineering teams to develop and implement software solutions, ensuring best practices and high-quality code. | Requires 7+ years of software engineering experience, leadership in multiple projects, and expertise in Ruby on Rails, which the candidate does not possess. | Title: Staff Software Engineer Location: Remote (United States) Department: Foundational Job Description: Root was founded on the belief that car insurance is broken, and we set out to change it. We’re harnessing the power of technology to revolutionize this archaic, complicated industry. Using machine learning and mobile telematic platforms, we’ve built one of the most innovative insurtech companies in the world. The Opportunity We are looking for a Staff Software Engineer to join and lead engineering at Root. As a Staff Engineer, you will be the primary technical leader for one or more teams within a product domain (e.g. Pricing, Underwriting, Claims, etc). You’ll work very closely with the software engineers on your team(s) to ship valuable software as well as the broad set of stakeholders to define the strategy and overall roadmap for the domain. Salary Range: $180,000 - $229,000 (Bonus and LTI Eligible) 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. How You Will Make an Impact Co-lead your team with your Engineering Manager, helping to coach, model for and grow the other team members. Partner with Product, Data Science, Analytics, and experts in the Insurance group to set the strategy for the quarters to come Identify and socialize important technical initiatives that increase the effectiveness of our products, systems, and teams Contribute code strategically each development cycle to advance the impact of the team Lead by example in incident response ensuring we take action to continuously improve the resiliency of our systems Coordinate with Staff Engineers across the organization to establish and evangelize standards and best practices What You Will Need to Succeed 7+ years as a software engineer 3+ years leading software teams Expertise in Ruby on Rails Familiarity with React Proven leadership of projects involving multiple teams across functional domains Excellent communication skills both with engineering 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.

Lead and optimize performance marketing systems using advanced machine learning techniques, managing a team of data scientists and engineers to improve marketing ROI. | Requires a PhD in a quantitative discipline, 7+ years industry experience with advanced quantitative methods, and 3+ years in leadership, with experience in large-scale marketing systems and AWS utilities. | The Opportunity We believe that a disruptive insurance company must have a principled quantitative framework at its foundation. At Root, we are committed to the rigorous development and effective deployment of modern statistical machine learning methods to problems in the insurance industry. At Root, the Data Science team owns the majority of all marketing capital allocation, using quantitative methods to test, maintain, and enhance our marketing strategies across numerous distribution channels. As a Senior Data Science Manager, Performance Marketing, you will drive continuous improvement of marketing strategies, channels, and operational processes while supporting the exploration of novel opportunities. You will lead a team of data scientists and machine learning engineers who design, deploy, and evolve the systems that power Root’s performance marketing engine. This includes optimizing bidding strategies, accelerating model iteration and deployment, and advancing applied R&D to improve how we capture and convert demand at scale. You will own the end-to-end measurement framework for performance marketing, ensuring rigorous measurement of business impact as media mix, partners, and tactics evolve. In this role, you will continuously raise the ceiling on how effectively Root turns marketing spend into value, while exploring new, deeper ways of engaging with marketing partners to unlock incremental performance. Root is a “work where it works best” company, meaning we will support you working in whatever location that works best for you across the US. We will continue to have our headquarters in Columbus to give more flexibility and more choice about how we live and work. Salary Range: $178,419 - $245,326 (Bonus and LTI eligible) How You Will Make an Impact Advance Root’s performance marketing engine through improved bidding strategies, automation, and applied machine learning Lead a team of 3-5 data scientists and machine learning engineers accountable for the deployment and performance of a nine-figure annual marketing budget Drive fast, disciplined experimentation across channels and partners, with clear measurement of incremental impact on growth and profit Make operationally critical decisions under uncertainty, balancing speed, risk, and rigor Partner with cross-functional leaders to influence priorities and deliver high-impact initiatives Define quarterly and annual roadmaps for performance marketing, translating business goals into prioritized modeling, measurement, and infrastructure enhancements Maintain a high standard of operational excellence across the team What You Will Need to Succeed Advanced degree in a quantitative discipline (PhD preferred) and 7+ years of applying advanced quantitative techniques to problems in industry 3+ years in a leadership role, with a track record of growing talent, scaling team impact, and delivering strategic outcomes Demonstrated experience building, validating, and applying statistical machine learning methods to industry problems Excellent command of AWS (or analogous) utilities, e.g., EC2, SageMaker, S3, Athena Excellent written and verbal communication skills: communicates effectively with technical and non-technical audiences Comfort leading across multiple concurrent initiatives while maintaining clarity and momentum Strong ownership mindset, proactively identifying high-impact opportunities and driving them through execution Ability to consider problems from first principles, with the instinct to use expertise and prior experience to guide but not dictate the solution Preferred but not required: Insurance industry experience Experience owning and operating systems that support large-scale customer acquisition Full funnel marketing experience: developing, executing, and measuring the impact of targeted, data-driven marketing strategies 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.

Develop and improve predictive models and machine learning solutions to enhance business outcomes. | Requires advanced quantitative skills, experience with statistical modeling, machine learning, Python, SQL, and industry experience, which are not present in your profile. | The Opportunity We believe that a disruptive insurance company must have a principled quantitative framework at its foundation. At Root, we are committed to the rigorous development and effective deployment of modern statistical machine learning (ML) methods to problems in the insurance industry. A Data Scientist II at Root is responsible for the end-to-end development of statistical methods and algorithms. This includes taking high-level business challenges, translating them into a concrete, quantitative framework, and shepherding solutions from R&D into production. Data Scientists typically work on cross-functional teams, regularly engaging with the members of various departments including Product, Engineering, and State Management. The Interventions data science team leverages ML techniques to target interventions that improve customer lifetime value, whether via mitigation of risk (e.g., fraudulent claims, bad debt) or by enhancing conversion and retention in our most profitable customer segments. We are looking for a Data Scientist II who will monitor and improve our suite of ML models, seek out new applications for ML to create business impact, and conduct rigorous experiments to validate new targeted interventions. Salary Range: $116,664 - $145,830 (Bonus and LTI Eligible) 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. How You Will Make an Impact Create robust predictive models for use in targeted interventions, using modeling techniques such as LightGBM Apply principled methods to translate model segmentation gains to improvements in key financial metrics Learn the required tools to get the job done, e.g., AWS (EC2, SageMaker, S3), Git, etc. Build data science pipelines to quickly iterate on research ideas and put them into production Effectively communicate insights from complex analyses Take end-to-end ownership of problem domains and continuously improve upon quantitative solutions What You Will Need to Succeed Advanced degree in a quantitative discipline (PhD preferred) and/or 2+ years of applying advanced quantitative techniques to problems in industry Strong demonstrable knowledge of topics such as statistical modeling, machine learning, and numerical optimization Exceptional communicator and storyteller with strong data visualization skills Strong programming skills with experience using modern packages in Python Experience with databases and SQL Demonstrated experience building, validating, and applying statistical machine learning methods to real world problems Ability to work independently with a strong ownership mentality, taking initiative to find, prioritize, and be accountable for the highest impact work Ability to frame functional problem statements for the next 1-2 months, consistently making good decisions about the right path to follow in a well-defined problem space Preferred but not required: Experience using version control (Git) and cloud computing (AWS) Insurance industry experience 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.

Support and develop agency relationships through outreach, onboarding, training, and feedback analysis to foster growth and engagement. | At least 1 year of experience with an insurance carrier or agency, proven success in outbound call campaigns, and strong communication and relationship-building skills. | The Opportunity As Root continues to expand their footprint in the Independent Agent space, we are looking for a Business Development Representative to help fortify the success of our fast-paced agency channel. In this role, you will be working closely with the business development team and other key internal stakeholders to advance our agent growth strategy and enhance our agent experience. Additionally, you will work closely with our agency partners to support them as they rapidly grow their book with Root. Salary Range: $55,000 - $67,000 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. How You Will Make an Impact Make outbound calls to independent agencies across the Root footprint with the goal of securing an appointment with them Manage the onboarding process for each appointment application Partner with the business to target key growth markets in the agency channel Host regular product training for new and existing appointed agents Conduct monthly/quarterly business reviews as needed with agency partners that drive new writings, premium and profit goals Drive agent engagement through continued agent education and experience enhancements Provide in-depth knowledge of Root’s underwriting and business appetite to agency partners Collaborate with internal and external business partners to drive product adoption and improvements Gather, classify, and analyze agent feedback for continuous improvements Participate in the development, maintenance, and consistent application of standard processes across agency onboarding Provide input for continuous development of department guidelines and best practices Leverage analytical business functions, including engineering, analytics, and product teams, to identify trends and opportunities to achieve favorable results Use independent discretion and judgment to consistently review business areas of opportunity Recommend viable solutions and alternatives to identified opportunities What You Will Need to Succeed At least 1 year of experience with an insurance carrier or an agency Thorough knowledge of insurance and the types of product offerings Root provides Proven success in agency outbound call campaigns Ability to build collaborative working relationships Communicate and collaborate effectively in a matrixed environment High sense of professionalism while remaining empathetic Great attention to detail Self-starter and ability to work independently and effectively prioritize work Effective written and oral communication skills Problem solver with a drive to “win” 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.

Lead and develop product managers overseeing distribution channels, drive product strategy, and execute cross-functional initiatives to optimize onboarding and distribution experiences. | 8+ years in product management with 2+ years managing PMs, experience in multi-channel distribution, API platforms, and working with sales or partner tools. | The Opportunity At Root, we’re reimagining car insurance by building a smarter, more equitable system from the ground up. We’re looking for a Manager II, Product Management to lead the PMs who own our distribution and onboarding experiences – including Independent Agents, Partnerships, and Direct-to-Consumer onboarding. This is a high-leverage role for a hands-on product leader who knows how to drive clarity and ship fast. You’ll coach PMs, align cross-functional teams, ensure each channel is delivering both customer and business impact, and get your hands dirty with special projects in the space. Salary Range: $168,000 - $200,000 (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. Who You Are Experienced manager: You’ve directly managed PMs and know how to develop talent, sharpen thinking, and raise the bar on product craft. Customer-centric: You advocate for our users across every distribution channel – from agents to partners to consumers – and know how to translate their needs into product direction. Distribution-minded: You’ve built or scaled products that power multi-channel distribution – ideally including B2B, B2B2C, and consumer funnels. Execution-first: You bias toward shipping, learning, and iterating. You design systems that remove friction, increase speed, and bring discipline to the product development and experimentation process. Analytical & data-native: You use data to drive decisions, test hypotheses, and calibrate strategy. You’re comfortable working with analysts, data scientists, and ML-driven systems. What You'll Do Drive Product Execution (50%) Own the end-to-end product strategy across our distribution ecosystem – including independent agents (direct + via comp raters), hosted and API partnerships, and direct onboarding flows. Drive roadmap clarity across multiple teams: ensure every PM knows the problem they are solving, the impact they are targeting, and how to measure success. Partner with Engineering, Design, Analytics, Business Development, and State Management to bring new distribution products and experiences to market. Set and maintain northstar metrics and OKRs across channels – balancing conversion, cost, partner needs, and long-term customer value. Push the organization to move fast: remove blockers, simplify decision-making, and enforce high standards for shipping quality work. People Management (50%) Manage and develop a team of 4-6 Product Managers across IA, Partnerships, and DTC onboarding. Coach PMs on problem definition, experimentation, hypothesis generation, and product craft. Establish a culture of rigor – teaching “why” before “how” and driving teams to own outcomes rather than output. Partner with cross-functional leaders to continually raise the bar on product quality, collaboration, and execution. Help scale the distribution product organization as Root grows into new markets and partner ecosystems. Preferred Experience 8+ years in Product Management, with 2+ years managing PMs Experience in multi-channel distribution, B2B/B2B2C integrations, or marketplace-style ecosystems Experience working with sales, partnerships, or agent-facing tools Strong understanding of funnel optimization, onboarding flows, and conversion strategy Experience with API-first platforms or embedded product experiences 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.