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