Deputy General Counsel
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.
- 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.