The Opportunity Root is seeking a senior legal leader to guide the company through increasing legal and regulatory complexity as we expand business development initiatives, explore corporate structure opportunities, and advance telematics and other technology-driven innovations. This role represents a strategic leadership opportunity as a people leader who is also a working manager, depending on the needs of the organization and the potential candidate's experience. As an execution-focused legal support team, this leader will operate at a senior leader level, shaping countrywide legal strategy, driving cross-functional alignment, and engaging directly with regulators to enable innovation. Operating at the intersection of executive decision-making and engagement with state insurance regulators, this leader will advise senior leadership on high-impact risks, align cross-functional partners on complex governance and capital matters, and lead regulatory engagement to enable responsible innovation. Success in this role means strengthening regulatory relationships, scaling compliance capabilities, and building the legal foundation that allows Root to grow confidently and competitively. Salary Range: $199,800- $249,700 (Bonus and LTI Eligible) 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, Ohio. For remote applicants, this position will require regular travel to Columbus, Ohio. How You Will Make an Impact - Advise executive leadership on legal and regulatory strategy shaping corporate structure, innovation, and long-term growth - Lead enterprise regulatory advocacy and represent Root in market conduct examinations, regulatory inquiries, and strategic negotiations - Define and oversee compliance risk management across multiple business functions - Align cross-functional leaders on complex governance, holding company, and regulatory priorities - Anticipate regulatory shifts, particularly in telematics and technology-enabled insurance models - Set strategic oversight for corporate licensing expansion, capital transactions (including Form D filings and extraordinary dividend notices), and other enterprise regulatory approvals - Design and evolve the Legal and Compliance organization to meet increasing complexity - Evaluate staffing, resource allocation, and departmental priorities to sustain high performance - Develop and coach Legal and Compliance leaders, strengthening long-term capability and succession readiness What You Will Need to Succeed - 12+ years of legal experience, including leadership roles within an insurance company or corporate environment, with substantial exposure to insurance regulation, holding company frameworks, capital transactions, or senior in-house leadership. - Demonstrated experience advising executive leadership on enterprise-level legal and regulatory strategy - Proven track record leading high-stakes regulatory engagement, including examinations, inquiries, and complex approval processes - Deep understanding of insurance holding company frameworks, capital transactions (including dividend and Form D approvals), licensing structures, and scalable compliance systems - Experience designing, scaling, and leading high-performing legal or compliance functions - Strong strategic judgment balancing product innovation, growth objectives, and evolving regulatory expectations - Ability to influence and align executive and cross-functional leaders through clear, persuasive communication on complex matters - Demonstrated ability to establish regulator trust and navigate scrutiny in highly visible or sensitive environments - High integrity and commitment to strengthening Root’s compliance culture 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 drafting, review, and negotiation of a wide range of commercial and corporate agreements, including customer, vendor, partnership, and strategic transactions. • Serve as the primary legal partner to the CFO, ensuring contracts align with revenue recognition, billing, risk allocation, and operational realities. • Independently negotiate against sophisticated counterparties, including Fortune 500 companies and global luxury and consumer brands. • Support global M&A activity, including due diligence, transaction execution, and post-acquisition integration. • Advise the CFO and executive team on legal risk, deal structure, and strategic tradeoffs in high-stakes negotiations. • Develop pragmatic, business-forward solutions that balance legal rigor with speed and growth. • Manage and coordinate outsourced legal counsel, including international firms and specialized advisors. • Ensure high-quality, cost-effective legal support across jurisdictions. • Build scalable processes for contract review, escalation, and risk management. • Help design and improve contract templates, playbooks, and internal processes to support rapid growth.

• Provide strategic direction in the drafting, review, and negotiation of a broad range of both strategic and day-to-day commercial agreements critical to the business. • Develop and implement contract templates, policies, and procedures to ensure high-quality, efficient legal operations. • Advise on trademark strategy and oversee the protection of Sunrun’s IP portfolio in commercial transactions. • Assist in the preparation of board and committee meeting materials, drafting resolutions, and coordinating agendas. • Stay up-to-date on corporate law developments and governance trends to ensure internal policies remain aligned with best practices. • Evaluate issues from both legal and business perspectives with a business-oriented approach to problem-solving. • Manage and oversee outside counsel with little direction.

• Provide day-to-day legal support on intellectual property and open source matters that shape how Airbnb builds, uses, and shares technology. • Advise on IP licensing and transactions and partner with cross-functional teams to strengthen open source governance and compliance. • Support Airbnb’s Tech Brand initiatives from concept through publication—providing legal review and practical risk guidance for external communications, technical storytelling, and developer- and community-facing programs. • Enable innovation and technology-focused storytelling with clear guardrails—supporting engineering velocity while protecting Airbnb’s brand, IP, and marketplace integrity. • Draft, review, and negotiate IP-related terms in commercial and intercompany agreements. • Partner with cross-functional stakeholders to identify repeatable IP issues and help build templates, guidance, and escalation paths that enable faster, more consistent decision-making. • Review and advise on external-facing Tech Brand materials, which may include blog posts, technical articles, and engineering announcements, conference talks, presentation decks, and speaker participation, and developer/community programs, events, and related communications.