Director, Finance Strategy and Operations

Overview:

SageSure, a leader in catastrophe-exposed property insurance, is seeking a Director, Finance Strategy and Operations to serve as a strategic partner to the Chief Accounting Officer. This role will drive key Finance initiatives, improve operating rhythms, strengthen decision readiness, and help the Corporate Finance organization scale effectively as the business grows.

What you’d be doing:

Executive Enablement & Strategic Partnership

Serve as a strategic partner and proxy for the CAO in key meetings, communications, and follow-up decisions

Manage executive priorities, workflows, and commitments to keep focus on the highest-impact enterprise priorities

Advise the CAO on organizational effectiveness, resource allocation, and strategic trade-offs

Decision Readiness & Information Management

Lead review and quality assurance for Finance and CFT executive materials, ensuring they are clear, accurate, and decision-ready

Maintain CAO dashboards and provide regular status readouts on priorities, risks, and commitments

Oversee month-end close progress, risks, and escalations, providing exception-based visibility and support

Synthesize information to accelerate decision-making and reduce rework

Cross-Functional Alignment & Integration

Drive strategic Finance initiatives that require coordination across Product, Underwriting, Legal, Compliance, Finance, and external partners

Maintain accountability and commitment tracking for the CAO organization

Establish operating mechanisms for progress tracking, risk escalation, and decision-making

Coordinate with external partners, including auditors and consultants, to manage visibility and escalation

Strategic Initiative Leadership

Own high-impact Finance priorities from planning through execution

Develop solutions to ambiguous, high-stakes challenges that influence organizational direction

Clarify goals, success measures, roles, risks, and outcomes for complex initiatives

Identify gaps in organizational systems and design practical solutions that help the CAO and CFT leadership operate more effectively

Influence, Relationship Management & Executive Presence

Build trusted relationships across the organization as a credible advisor to senior leaders and key stakeholders

Influence outcomes and align teams without direct authority

Navigate complex interpersonal and organizational dynamics with diplomacy, professionalism, and sound judgment

Facilitate productive discussions, resolve conflicts, and build consensus across stakeholder groups

Demonstrate strong executive presence, communication skills, and emotional intelligence

Documentation & Communication

Capture key insights, decisions, and follow-ups from CAO-designated executive meetings

Document critical processes, decisions, and strategies so they are clear and accessible

Create and maintain materials that support scaling, onboarding, and cross-functional alignment

Translate operational complexity into clear narratives that support alignment and decision-making

Organizational Effectiveness & Continuous Improvement

Improve executive operating systems, accountability frameworks, and decision-readiness processes

Champion continuous improvement and innovation within the Finance organization

Provide strategic guidance and mentorship to Finance team members

Model SageSure values and promote a culture of trust, respect, accountability, and collaboration

We’re looking for someone who has:

10+ years of progressive experience in finance operations, strategic operations, chief of staff, or related roles

Deep understanding of financial principles, processes, reporting, and executive decision cycles

Proven ability to lead complex, high-impact initiatives independently in a matrixed environment

Strong executive presence, communication skills, and ability to build credibility with senior leaders

Exceptional influencing, stakeholder management, and relationship-building skills

High emotional intelligence, discretion, and sound judgment in sensitive or ambiguous situations

Experience developing accountability systems, operating mechanisms, and organizational frameworks

Experience supporting C-level executives in high-growth or scaling organizations

Highly preferred candidates also have:

Experience in insurance, financial services, or another highly regulated industry

Background in management consulting, strategic operations, or a formal Chief of Staff program

MBA or relevant advanced degree

#LI-Hybrid 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.

California Applicants: View SageSure’s Workforce Members’ Privacy Notice - CA Privacy Policy & Notice of Collection