Senior Director, Strategy

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

We are looking for a Senior Director of Strategy to join our Business Development team. This is a pivotal leadership role responsible for building, scaling, and leading Root’s Independent Agent (IA) business—this is a vertical that is growing at an incredible rate, with line of sight to a $1B+ book.

This individual will serve as the business leader for Root’s IA distribution, responsible for both strategic and operational leadership. You will scale the team to 30+ employees within the next year, establish organizational design, and build the infrastructure to sustain profitable growth. You will bring deep expertise in the IA channel, paired with carrier-side experience, to ensure Root is positioned as a differentiated, agent-first carrier of choice.

Root is a “work where it works best” company. This means we will support you working in whatever location that works best for you across the US.

Salary Range: $180,000 - $225,000 (Bonus & LTI Eligible)

How You Will Make an Impact

• Business Leadership: Serve as Root’s executive owner for IA distribution, managing a large book with responsibility for growth, profitability, and scaling to $1B+.
• Team Building: Design, recruit, and lead a team of 30+ employees across account management, operations, enablement, and partner engagement, instilling a high-performance and agent-first culture.
• Strategic Growth: Define and execute the IA channel strategy, including segmentation by agency size (small, mid, large, jumbo), onboarding jumbo agencies, and expanding comparative rater integrations.
• Operational Excellence: Architect and implement scalable processes for agent appointment, commissions, servicing, annual incentives, and engagement to meet the demands of rapid expansion.
• Carrier & Agent Expertise: Leverage deep industry experience to balance the needs of independent agents, ensuring Root’s offerings are competitive, compliant, and easy to work with.
• Cross-Functional Influence: Partner with product, engineering, finance, actuarial, legal, and marketing to align IA priorities with Root’s enterprise goals.
• Thought Leadership: Act as the internal and external voice of Root’s IA strategy, representing the company with senior industry stakeholders, national agencies, and technology partners.

What You Will Need to Succeed

• 12+ years of progressive leadership experience in the insurance industry with significant time spent in the independent agent channel.
• Direct experience on the carrier side, understanding P&L ownership, distribution strategy, and scaling IA business lines.
• Ability to design, scale, and lead large teams through periods of rapid growth (from small teams to 30+ employees).
• Strong track record of signing, onboarding, and growing relationships with jumbo agencies and building tooling and enablement.
• Demonstrated success in building unit economics, bonus structures, incentive programs, and operational frameworks for IA distribution.
• Ability to balance strategic vision with hands-on execution—building the long-term playbook while delivering immediate results.
• Deep relationships and credibility across the IA landscape; strong ability to represent Root as a carrier of choice in the market.
• Entrepreneurial mindset with a customer-first orientation and a proven ability to innovate within established industry frameworks.
• Exceptional collaboration, influence, and communication skills, with experience operating at the executive level.

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