Deputy General Counsel

Root Insurance

8d•Remote

About The Position

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.

Requirements

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

Responsibilities

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

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