Root Insurance Agency

• Build and improve the systems that power customer lifetime value modeling, from development and deployment through monitoring and production support. • Partner with data scientists to productionize statistical models, simulations, and forecasting workflows that support decision-making across the business. • Accelerate the path from research to production through scalable infrastructure, reliable workflows, and reusable tooling. • Improve the ML development experience by building better operational patterns and advancing production-ready ML practices. • Develop tools and services that help stakeholders evaluate model performance, understand business impact, and trust model outputs in production. • Collaborate with technical and business partners to solve high-value problems and improve the reliability and scalability of ML systems. • Share best practices through mentorship, documentation, and clear communication around technical decisions, tradeoffs, and operational considerations.

• Drive end-to-end execution of large-scale, strategic initiatives that materially improve business outcomes (e.g., revenue, loss ratio, customer experience). • Align leaders and teams around high-value initiatives, ensuring clarity on priorities, tradeoffs, and expected impact. • Make and influence decisions on organizational structure, team topology, and resource allocation to enable successful execution of critical initiatives. • Set and guide priorities across multiple teams and domains, balancing short-term delivery with long-term scalability and resilience. • Lead cross-functional collaboration with Product, Data Science, and business stakeholders to translate strategy into coordinated execution. • Establish and evolve technical standards, architecture, and best practices that scale across the organization. • Communicate complex technical and strategic concepts to drive decision-making and alignment at the executive level. • Coach and influence engineering leaders and senior ICs, raising the organization’s ability to identify opportunities and deliver business impact at scale. • Coordinate with Staff Engineers across the organization to establish and evangelize standards and best practices.

• Lead compensation strategy, including market evaluations, job architecture, salary structures, and compensation program design and administration. • Serve as a trusted advisor and subject matter expert on compensation, benefits, payroll, leave administration, and total rewards best practices. • Oversee benefits strategy and administration, including vendor partnerships, renewals, open enrollment, employee experience, and regulatory compliance. • Lead payroll and leave administration operations to ensure accurate, timely, compliant, and employee-centered processes. • Partner closely with Talent Acquisition and business leaders to support competitive offers, organizational design, and workforce planning decisions. • Build and maintain reporting and analytics to support pay equity, market competitiveness, and data-driven decision-making. • Drive operational excellence through process improvement, automation, systems optimization, and scalable workflows. • Lead and maintain executive compensation initiatives, equity administration, and Board/Compensation Committee-related activities.

• Own the end-to-end IR operating cadence, including earnings preparation, shareholder letter drafting, scripts, Q&A, and cross-functional coordination. • Translate Root’s strategy, financial performance, and product evolution into clear, compelling, and consistent external messaging. • Develop and refine Root’s investor narrative, positioning the company as a technology-driven platform while connecting near-term performance to long-term value creation. • Lead the creation of high-quality investor-facing materials that drive engagement across institutional and retail audiences. • Partner cross-functionally with Finance, Product, Data Science, Engineering, Business Development, and Marketing to synthesize insights into investor-ready narratives. • Support investor and analyst engagement, including preparation, follow-ups, conferences, and ongoing dialogue. • Prepare the Head of IR and executive team for high-impact interactions, ensuring clarity, consistency, and depth of messaging. • Anticipate investor questions and pressure-test messaging to ensure credibility in complex discussions. • Partner closely with Communications and PR to develop a unified external narrative across investors, media, and retail audiences while increasing Root’s visibility and engagement in the market. • Monitor investor sentiment, peer positioning, and market dynamics to continuously improve how Root is understood and valued. • Mentor and develop junior IR talent by creating structure, providing feedback, and helping build deeper business and market fluency across the team.

• Lead the drafting and negotiation of innovative partnership and strategic initiative agreements across the insurance ecosystem. • Serve as embedded counsel to the Business Development team on insurance agency agreements, joint ventures, partnerships, and other strategic opportunities. • Identify, assess, and mitigate legal and business risk through thoughtful contract drafting, negotiation strategy, and practical counseling for internal stakeholders. • Provide clear, actionable legal guidance to senior management and internal stakeholders on insurance regulatory requirements across all 50 states, including statutory and administrative regimes, as well as applicable federal laws and regulations such as GLBA. • Partner with Legal, Compliance, Internal Audit, Claims, Product, Data Science, and State Management to align on risk-based approaches to new and emerging programs led by the Business Development team. • Prepare high-quality, decision-ready written analyses to support leadership in strategic planning, risk assessment, and issue escalation. • Provide practical, timely legal guidance to teams building new products and services across traditional and digital distribution channels. • Work closely with cross-functional partners through all phases of product development, implementation, and rollout. • Translate evolving regulatory and commercial developments into pragmatic recommendations and risk management strategies.

• Test, maintain, and enhance our marketing strategies across numerous distribution channels. • Expand and diversify Root’s direct marketing portfolio by shepherding new mid-upper funnel channels from R&D to production. • Rapidly prototype, test, and iterate on novel marketing strategies in the mid and upper funnel. • Design time- and cost-efficient A/B tests that enable rigorous measurement of the incremental profit impact of marketing campaigns. • Deliver clear and prompt communication of research results that drive action to leaders and stakeholders.

• Partner with senior leaders in Engineering and Product to drive strategic initiatives and organizational decisions • Analyze data and provide clear recommendations to inform leadership decisions • Influence stakeholders across functions to align on priorities and execution • Manage multiple high-impact initiatives in a fast-changing environment • Help leaders improve team effectiveness, structure, and performance

• Lead the development and execution of integrated marketing campaigns supporting both Independent Agents and strategic partners • Drive agent acquisition and retention efforts through coordinated, multi-channel programs • Collaborate with Partnerships team to support co-marketing initiatives with OEMs and other partners • Build and optimize audience strategies, messaging, and campaign journeys across the funnel • Align marketing efforts across internal teams to ensure consistency and maximize impact • Manage external vendors, platforms, and partner relationships to deliver effective programs • Translate performance insights into actionable recommendations to improve campaign effectiveness • Communicate results, learnings, and strategic recommendations to stakeholders and leadership

• oversee the strategy and handling of complex cases • direct projects and initiatives related to major case and provider fraud initiatives • monitor trends with lawsuit filings for FPM and Injury • engage in coaching appropriate behaviors with leaders

• 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