Director, Office of the CEO

SageSure • Mountain View, CA

3d • Onsite

About The Position

SageSure is seeking a Director, Office of the CEO to serve as the Chief of Staff’s closest partner and direct backup. The role creates leverage for the CEO by owning a portfolio of high-priority cross-functional initiatives, managing the Office of the CEO’s review rhythm, co-leading Board preparation, and turning early ideas into executive-ready work. The successful candidate is a polished, high-emotional-intelligence operator with structured thinking, sound judgment, exceptional communication, and a willingness to personally develop materials and analyses. The position requires working on-site five days per week in SageSure’s Mountain View, California office, responding outside standard business hours when business requirements warrant, and periodic travel for Board and partner meetings.

The Director owns five to seven CEO-priority projects from problem framing and fact-finding through recommendations, governance, implementation, and measurable close-out. The role runs the Office of the CEO’s operating rhythm, co-leads Board preparation and production, and serves as the Chief of Staff’s backup to keep decisions and deliverables moving. It also involves creating executive-quality presentations, prototypes, analyses, action plans, speeches, town hall content, and talking points; representing the office with senior internal and external stakeholders; and driving accountability across functions without formal reporting authority.

SageSure is a growing managing general underwriter focused on catastrophe-exposed property insurance. Founded in 2009, the company operates in 16 states, offers more than 110 home, flood, and commercial products, manages more than $3.2 billion of inforce premium, and helps protect more than 970,000 policyholders. It has more than 1,000 employees across 12 offices and is an Equal Opportunity Employer committed to belonging and inclusion.

Requirements

• Approximately seven to ten years of total professional experience, including four to seven years in management consulting, investment banking, or a similarly demanding environment.
• Broader strategy, corporate development, strategic finance, or operating experience that has built strong judgment, executive presence, and the ability to navigate senior stakeholders.
• Demonstrated ownership of complex, ambiguous, cross-functional work with limited direction and clear accountability for results.
• Exceptional PowerPoint and written communication skills, with the ability and willingness to personally create executive-quality materials.
• Strong analytical and problem-solving capabilities, including building a fact base, synthesizing complex information, and translating analysis into clear recommendations and executable plans.
• High emotional intelligence, discretion, responsiveness, and comfort interacting directly with a CEO, Board members, and senior internal and external stakeholders.
• Ability to operate with urgency, manage competing priorities, and maintain accuracy and sound judgment in high-stakes settings.
• Ability to work in the Mountain View office five days per week, respond outside standard business hours when business requirements warrant, and travel periodically for Board and partner meetings.

Nice To Haves

• Experience in insurance, reinsurance, financial institutions, or another regulated financial-services environment.
• Experience supporting Board, investor, or other senior external stakeholder materials and interactions.
• Hands-on experience using AI tools to accelerate research, drafting, analysis, and prototyping.

Responsibilities

• Own five to seven CEO-priority projects, framing ambiguous problems, building the fact base, developing recommendations, navigating governance, and driving implementation and measurable close-out.
• Run the Office of the CEO operating rhythm by managing intake, reviewing deliverables before they reach the CEO, working through the review list with the CEO, accurately capturing feedback, and ensuring owners close the loop.
• Co-lead SageSure Board preparation, including owning major sections and the production process, harmonizing executive inputs, maintaining version control, reconciling content and numbers, anticipating questions, and tracking follow-ups.
• Serve as the Chief of Staff’s direct backup and act as the CEO’s in-person partner when the Chief of Staff is unavailable, keeping decisions, deliverables, and the review rhythm moving.
• Personally create executive-quality presentations, working prototypes, analyses, action plans, CEO speeches, town hall content, and talking points.
• Represent the Office of the CEO professionally and credibly with executives, Board members, investors, reinsurers, carrier and distribution partners, and other senior external stakeholders.
• Drive accountability across senior leaders and functions without formal reporting authority, escalating blockers and ensuring commitments are completed.
• Complete ad hoc projects and other duties needed to help drive SageSure’s purpose and fulfill its values.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed