Chief of Staff to the CEO na Root Insurance

CURRENT ROOT EMPLOYEES - Please apply using the career page in Workday. This career site is for external applicants only.

The Opportunity

The Chief of Staff (CoS) will maximize the CEO’s effectiveness by managing operational, communication, and strategic initiatives. As a confidante, advisor, and sounding board to the CEO, the CoS will drive clarity, accountability, and alignment across the organization. The CoS builds collaborative relationships with the Executive Leadership Team (ELT) to advance strategic priorities and ensure business results are delivered. This role is operational and strategic with no task being too mundane or too difficult.

Salary Range: $270,000 - $300,000 (Also eligible for competitive bonus and equity offering)

How You Will Make an Impact

Strategic Execution & Prioritization

• Translate strategic initiatives into structured plans, executive briefs, and accountability check-ins. This includes OKRs, departmental initiatives, and board-level deliverables.
• Lead the planning and facilitation of investor updates, executive sessions, press interviews, staff meetings, offsites, and executive retreats. Responsible for agenda development, content curation, day-of logistics, translating outcomes into actionable follow-ups, and tracking their progress.
• Own and maintain the CEO’s to-do list, proactively delegating, advancing tasks, or removing roadblocks. This includes representing the CEO in meetings when necessary.
• Act as an amplifier of the CEO’s priorities and communication, ensuring alignment across teams.
• Partner with the CEO’s executive assistant to anticipate scheduling needs and prepare the CEO with context, talking points, and key documentation.
• Project manage key planning cycles (e.g., annual business planning, executive retreats, quarterly reviews).

Organizational Alignment

• Act as a thought partner and connector between the CEO and senior leadership.
• Anticipate cross-functional blockers and proactively resolve operational misalignments.

Communication & Documentation

• Prepare internal and board-facing communications, briefings, and executive updates.
• Write concise and clear strategic memos, CEO updates, and one-page executive summaries that clarify intent and drive aligned execution.
• Lead the coordination, development, and distribution of materials and briefings for Board of Directors meetings, ensuring all content is comprehensive, polished, aligned with strategic messaging, and delivered in a timely manner.

What You Will Need to Succeed

Experience

• 7+ years in management consulting, strategic operations, business planning, or high-growth startups with at least 5 years of leadership experience.
• Bachelors degree required, MBA preferred.
• Proven success managing fast-paced, multi-stakeholder executive environments.
• Track record of breaking down complex, ambiguous challenges into actionable strategies and driving measurable outcomes.
• Strong financial acumen and comfort interpreting operational KPIs.
• Experience managing or coordinating high-profile deliverables (e.g., board materials, investor decks, CEO communications).
• Familiarity with operating rhythms in founder-led environments and comfort with high-stakes decision-making under pressure.
• Experience navigating business organizations, managing multiple cross-functional stakeholders, and negotiating optimal solutions benefiting all parties.

Skills

• Strong project management, oral and written communication, and organizational skills.
• Ability to drive and implement ideas in an agile environment.
• Structured thinker who can operate at both 30,000 feet and ground level.
• Advanced skills in Notion, Excel/Sheets, presentation software, and project management tools.
• Comfortable using data to drive insights, with a high degree of business acumen and judgment.
• Highly organized and detail-oriented; relentless in follow-through and able to manage multiple workstreams simultaneously.
• Strong ability to push back and influence effectively

Don’t meet every single requirement?

Studies have shown that women and people of color are less likely to apply to jobs unless they meet every single qualification. At Root, Inc., we are dedicated to building a diverse and inclusive workplace, so if you’re excited about this role but your past experience doesn’t align perfectly with every qualification in the job description, we encourage you to apply anyway!

Join us

At Root, we judge people based on the merit of their work, not who they are. If you are passionate about what this role entails and solving real problems, we encourage you to apply. We want to learn about you and what you can add to our team.

Who we are

We’re harnessing the power of technology to revolutionize insurance. Using machine learning and mobile telematic platforms, we’ve built one of the most innovative FinTech companies in the world. And we’re just getting started.

What draws people to Root

Our success is in large part due to our unwavering standards in hiring. We recognize that our products are only as good as the people building and promoting them. We want individuals who find solutions by going through the cycle of ideation to implementation with curiosity, rigor, and an analytical lens. Ask anyone who works here and you’ll hear similar reasons for why they joined:

Autonomy—for assertive self-starters, the opportunities to contribute are limitless.

Impact—by challenging the way it’s always been done, we solve problems that have a big impact on our business.

Collaboration—we encourage rich discussion and civil debate at every turn.

People—we are inspired by the collection of crazy-smart people around us.