Root was founded on the belief that car insurance is broken, and we set out to change it. We’re harnessing the power of technology to revolutionize this archaic, complicated industry. Using machine learning and mobile telematic platforms, we’ve built one of the most innovative insurtech companies in the world.
The Opportunity
Root is seeking a Senior Director, Total Rewards to lead the strategy, development, implementation, and ongoing optimization of the company's compensation, benefits, payroll, and leave administration programs. In this role, the leader will partner closely with the VP, People to align Root’s total rewards strategy with the broader enterprise people vision, while serving as a trusted subject matter expert across compensation, benefits, payroll, and executive compensation.
This leader will oversee and evolve Root's total rewards philosophy and infrastructure to ensure the company remains competitive in attracting, retaining, and rewarding exceptional talent. The Senior Director will also play a key role in driving operational excellence across People processes, leveraging systems, automation, and scalable workflows to improve efficiency, compliance, and the employee experience in a fast-paced environment.
In addition, this individual will partner closely with Talent Acquisition to support fair and market-competitive offers, ensure consistency and equity across compensation decisions, and support executive compensation and Board-related activities.
Salary Range: $195,800 - $244,800 (Eligible for competitive bonus and equity offering)
Root is a “work where it works best” company, meaning we support employees working in the location that works best for them across the continental U.S. We will continue to maintain our headquarters in Columbus, Ohio, with a preference for Columbus-based candidates.
How You Will Make an Impact
- 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.
What You Will Need to Succeed
- Bachelor’s degree in business, finance, HR, or a related field.
- 10+ years of progressive experience in compensation or total rewards leadership.
- Expertise in compensation strategy, market data, benefits administration, payroll operations, leave administration, and job architecture.
- Strong understanding of applicable compensation, payroll, benefits, and leave regulations and best practices.
- Strong analytical and problem-solving capabilities with experience working with complex datasets and translating insights into action.
- Collaborative leadership style with the ability to build trusted partnerships and influence stakeholders across the organization.
- Experience with HRIS, payroll, and compensation systems; Rippling experience preferred.
- Excellent communication skills, sound judgment, and ability to manage highly sensitive information with professionalism and confidentiality.
- Ability to prioritize effectively and thrive in a dynamic, fast-paced environment.
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 [email protected]
Skills Required
- Bachelor's degree in business, finance, HR, or a related field
- 10+ years of progressive experience in compensation or total rewards leadership
- Expertise in compensation strategy, market data, benefits administration, payroll operations, leave administration, and job architecture
- Strong understanding of applicable compensation, payroll, benefits, and leave regulations and best practices
- Strong analytical and problem-solving capabilities with experience working with complex datasets
- Collaborative leadership style with ability to build trusted partnerships and influence stakeholders
- Experience with HRIS, payroll, and compensation systems; Rippling experience preferred
- Excellent communication skills, sound judgment, and ability to manage sensitive information confidentially
- Ability to prioritize effectively and thrive in a dynamic, fast-paced environment
What We Do
At Root, we’re doing things differently. We’re reimagining the services people need so that they serve them better. And we’re doing it by using data, technology, and rapid innovation to create products and experiences that are fair, easy, personal, and affordable. We’ve partnered with Carvana in a partnership that brings an industry-leading, seamless insurance process to the online car buying experience. The launch of Carvana Insurance Built with Root delivers an elevated customer experience made possible through a deep integration that pre-fills key customer information so that a customer can skip data entry and jump directly to evaluating quotes and customizing coverage. This fully embedded product experience—from quote to payment—happens entirely within the Carvana checkout process. Teams from both Carvana and Root have worked for months to build this bold technology platform. An early iteration involved 24 screens in the customer experience flow—that experience is now just three straightforward steps.
Why Work With Us
Our success is because of the hard work, ingenuity, and exceptional performance of our team. People come to Root because they know they can make an impact in their role, the company, and the industry. We’re passionate and curious self-starters, building a top-notch customer experience. Sound like something you’d like to be a part of?
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