Root Inc.

• Delivers an industry-leading claim experience for all policyholders and claimants • Negotiates and settles total loss situations with policyholders and claimants • Prepares salvage vehicles for auction and oversees the end-to-end salvage process • Consistently makes prompt and courteous contact with every claim customer • Maintains and updates a diary/schedule for each claim in the adjuster’s pending • Responds to claim correspondence in a timely fashion with very high quality • Provides input for continuous development of claims guidelines and best practices • Recommends potential product developments and process improvements • Interacts and communicates effectively with customers, peers, vendors and managers • Engages in learning opportunities to build knowledge of personal lines claims, court decisions impacting the claims function, current guidelines in claims function, and policy changes and modifications.

• Advance Root’s performance marketing capabilities through improvements in bidding systems, automation, and applied machine learning • Lead and develop a multidisciplinary team responsible for the deployment, optimization, and performance of a nine-figure annual marketing budget • Drive fast, disciplined experimentation across channels and partners • Develop strategic relationships with marketing and technology partners • Align priorities across Marketing, Analytics, Engineering, and Product

• Drive results - develop, enhance and maintain the auto product in assigned states; methodically set rate levels, customize franchise products, inform underwriting decisions, manage state idiosyncrasy, and pursue project timelines to achieve profitable growth • Analyze performance - develop reporting and maintain awareness of key performance indicators as they develop in assigned states, escalating concerns and recommending adjustments as required; provide and socialize analytical expertise across the broader state management team • Navigate the competitive landscape - understand emerging market trends, competitor products, customer needs, and regulatory requirements • Manage external relationships - manage relationships with Departments of Insurance and other stakeholders during filings, market conduct exams, and as we refine and advance our insurance products • Collaborate across organization - establish relationships with marketing, claims, underwriting, and distribution teams to ensure productive outcomes for those functions within assigned markets; keep key stakeholders informed regarding status of notable initiatives

• Lead and oversee reinsurance accounting activities including month-end close, journal entries, account analysis, reconciliations, and complex reinsurance transactions. • Own the relationship, preparation, review, and completion of reinsurance reports for brokers, management, reinsurers, auditors, internal cross-functional partners, fronting arrangements, and other stakeholders. • Support accurate and timely GAAP, statutory, SEC, quarterly, and annual financial reporting. • Assist with statutory accounting statements, state filings, and other regulatory reporting requirements related to statistical reporting, reinsurance and insurance accounting. • Develop, maintain, and improve reinsurance accounting procedures, close processes, reconciliation templates, reporting workflows, and control documentation. • Identify, document, and enhance key controls related to reinsurance accounting, reconciliations, statutory reporting, and financial reporting. • Drive process improvements, automation, reconciliation enhancements, and scalable reporting solutions. • Partner cross-functionally to improve data quality, reduce manual effort, strengthen controls, and shorten the close timeline. • Lead, influence, develop, and grow the existing team through clear direction, coaching, training, and performance development. • Navigate ambiguity, coordinate multiple projects simultaneously, accept ownership and accountability, and deliver on commitments. • Support ad hoc accounting, reporting, regulatory, audit, and strategic finance projects as needed.

• Set the short and long term strategy for the Data Platform in partnership with Qualitative Science, Decision Science and Product • Effectively manage the individuals on your team to ensure they are performing well in their role and as members of the team • Use an appropriate mixture of coaching, directive feedback, and delegation to achieve business, team and individual goals • Identify gaps in the team and develop plans to address those gaps via individual development, hiring, or partnership • Proactively dive into code, design reviews, and technical challenges alongside your team when necessary • Work closely with the Engineering Leadership team to improve the effectiveness of the Engineering org as a whole

• 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.