Director, Office of the CEO

Overview 

If you're looking for the stability of a profitable, growing company with the entrepreneurial spirit of a startup, we're hiring. SageSure, a leader in catastrophe-exposed property insurance, is seeking a Director, Office of the CEO. This highly visible role is the Chief of Staff's closest partner and direct backup, creating leverage for the CEO by owning a portfolio of the company's highest-priority cross-functional initiatives, running the Office of the CEO's review rhythm, co-leading Board preparation, and turning early ideas into executive-ready outputs. The successful candidate will be a polished, high-EQ operator who combines structured thinking, sound judgment, exceptional communication, and a willingness to personally build the materials and analyses needed to move important work forward. This role requires five days per week on-site in our Mountain View, CA office.

What you'd be doing: 

• Own a portfolio of five to seven CEO-priority projects, framing ambiguous problems, building the fact base, developing recommendations, navigating governance, and driving work through implementation and measurable close-out.


• Run the Office of the CEO operating rhythm by managing intake, reviewing deliverables before they reach the CEO, working the review list directly with the CEO, capturing feedback accurately, 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, acting as the CEO's in-person partner when the Chief of Staff is unavailable and keeping decisions, deliverables, and the review rhythm moving without interruption.


• Turn ideas into action by personally building 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 relying on formal reporting authority, escalating blockers and ensuring commitments are completed.


• Complete ad hoc projects as they arise and perform other duties needed to help drive SageSure's purpose and fulfill its values.

We're looking for someone who has: 

• 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 the ability to build a fact base, synthesize complex information, and translate 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.

Highly preferred candidates also have: 

• 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.

About SageSure:

Named among the Best Places to Work in Insurance by Business Insurance for four years in a row (2020-2023), SageSure is one of the largest managing general underwriters (MGU) focused on catastrophe-exposed property in the US. Since its founding in 2009, SageSure has experienced exceptional growth while generating underwriting profits for carrier partners through hurricanes, wildfires, and hail. Available in 16 states, SageSure offers more than 110 home, flood, and commercial products on behalf of its highly rated carrier partners. Today, SageSure manages more than $3.2 billion of inforce premium and helps protect more than 970,000 policyholders.  

 We have more than 1,000 employees in a distributed workforce environment across 12 offices—Fairfield, CA; Mountain View, CA; Cheshire, CT; Jacksonville, FL; Tallahassee, FL; Tampa, FL; Chicago, IL; Jersey City, NJ; Marlton, NJ; Cincinnati, OH; Houston, TX; Sheboygan, WI—who are tackling the industry’s toughest challenges.     

SageSure is a proud Equal Opportunity Employer committed to building a workforce that reflects the spectrum of perspectives, experiences, and abilities of the world we live in. We recognize that our differences make us strong, and we actively seek out diverse candidates through partnerships with organizations, institutions and communities that represent various backgrounds. We champion belonging and inclusion for all identities, including, but not limited to, race, ethnicity, religion, sexual orientation, age, veteran status, ability status, gender, and country of origin, striving to create a culture where all individuals feel valued, respected, and empowered to bring their authentic selves to work. 

Our nimble, highly responsive culture nurtures critical thinkers who run toward problems and engineer solutions. We relentlessly pursue better outcomes by investing in the technology, talent, and tools that position us to succeed in demanding markets. Come join our team! Visit sagesure.com/careers to find a position for you. 

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