Finance Strategy and Operations Director
About the job
- 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
- 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
- Lead review and quality assurance for Finance and Corporate Finance Team (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
- 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
- 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
- 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
- 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
- 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
- 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
About the company
SageSure provides homeowners and small business insurance in high-risk coastal areas that traditional insurers often overlook. It offers tailored insurance products for underserved markets and relies on experienced professionals in underwriting, product development, sales, technology, and customer service to serve these clients. The company uses data analytics and risk assessment to price policies competitively while maintaining quality coverage, achieving profitability through underwriting premiums. SageSure’s goal is to ensure reliable, affordable protection for customers in coastal risk zones by focusing on niche markets, expert guidance, and personalized service rather than generic coverage.
Company Size
501-1,000
Company Stage
Debt Financing
Total Funding
$1.7B
Headquarters
Jersey City, New Jersey
Founded
2009
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Simplify's Take
What believers are saying
- March 2026 Seawall Re II raised $200 million, lifting sidecar capital to $250 million.
- February-March 2026 Gateway Re deals totaled $845 million, proving investor demand.
- SageSure now manages $3.2 billion inforce premium and 970,000 policyholders across 16 states.
What critics are saying
- SageSure sued MapleSage on June 12, 2026 over sagesure.io brand theft.
- One severe 2026 hurricane season can exhaust reinsurance layers and trigger carrier retreat.
- Florida, Louisiana, Texas, and South Carolina concentration makes SageSure hostage to catastrophe clustering.
What makes SageSure unique
- SageSure ranked third-largest catastrophe bond sponsor globally by March 2026.
- Seawall Re and Gateway Re give SageSure proprietary capital-markets distribution for coastal risk.
- Gemini and Olympus added Florida depth, 130,000 policies, and 1,500 independent agents.
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Benefits
Fully stocked cafés with free snacks and beverages
Lounges with shuffleboard, billiards and board games
Access to in-office gyms
Organized and ad hoc social events
Medical (HSA, EPO, PPO)
Dental
Vision
401(k) with company match
Profit-sharing bonus program
Life insurance
Short-term and long-term disability
Up to 160 hours of paid time off per year, plus floating holidays
Paid holidays
8 hours of volunteer time off per year
Gym reimbursement
Tuition reimbursement toward education, licensing and certifications
Employee assistance program with access to free and confidential counseling
Growth & Insights and Company News
6 month growth
↑ 13%1 year growth
↑ 13%2 year growth
↑ 14%SageSure wins Core category at Datos Insights 2026 Insurance Technology Impact Awards for proprietary compliance platform. Internally developed Surplus Lines Insurance Management (SLIM) platform recognized for its end-to-end automation and less than 1% filing error rate. CINCINNATI, OH - September, 2026 - SageSure, the largest residential property MGU in the US specializing in catastrophe-exposed markets, today announced that its proprietary Surplus Lines Insurance Management (SLIM) platform won the Core Systems Innovation category in the 2026 Datos Insights Insurance Technology Impact Awards. The Datos Impact Awards are the industry's premier peer-juried recognition program for insurance technology leaders. Evaluated anonymously by the Datos Insights Insurance Technology Executive Council - a panel of peer CIOs with direct enterprise modernization experience - the Core category recognizes market-leading initiatives that transform essential technology systems, including policy administration, underwriting, and billing. Developed by SageSure's internal platform engineering and surplus lines teams, SLIM automates multi-state regulatory compliance across the high-growth surplus lines market. Historically, disparate state stamping office mandates require intensive manual oversight and post-bind reconciliation. SLIM eliminates this structural friction by converting each policy event into an auditable regulatory filing, validating licenses via NIPR integration, and applying explainable AI (xAI) document verification before filings ever reach a state stamping office. "The best insurance technology is built by teams who deeply understand the operational realities of the business," said Terrence McLean, President and CEO of SageSure. "Our engineering and surplus lines teams built an internal solution that immediately made our operations faster, more compliant, and more scalable. It's an honor to see this work recognized by leaders who appreciate both the complexity of the challenge and the sophistication of the solution." Since its initial rollout, SLIM has set a new benchmark for SageSure's regulatory throughput: * Automates 90% of monthly filing transactions while processing tens of thousands of policy events. * Maintains a near-zero defect rate across state submissions, virtually eliminating late-filing friction. Currently live in California and New York, SLIM will expand to Florida and Texas in the coming months to support hundreds of millions in written premium. "Surplus lines compliance is notoriously complex, and traditionally reliant on manual, retroactive review," said Al Bagiro, AVP of Surplus Lines at SageSure and executive sponsor of SLIM. "We engineered SLIM on a foundational rule: validation must happen before a filing leaves the building, not after a regulator rejects it. This recognition validates both the platform and the agile, in-house team that modernized critical infrastructure to deliver enterprise-grade accuracy at scale." About SageSure SageSure is the largest residential property MGU in the US specializing in catastrophe-exposed markets. Dedicated to serving producers and carrier partners, SageSure provides highly differentiated residential and commercial solutions, innovative service and claims management, and market-leading buying experiences. A leader in catastrophe risk underwriting and exposure management, SageSure operates in 16 states, protects nearly 1 million policyholders, and manages more than $3.3 billion of inforce premium. For more information, visit sagesure.com. About the Datos Insights Impact Awards Datos Insights is a leading provider of research, advisory, and consulting services to the financial services, insurance, and retail technology industries. Its Impact Awards recognize insurers, banks, and technology companies for projects that deliver measurable business results, as selected by councils of peer executives with direct experience leading complex technology initiatives. Past honorees across Datos Insights' Impact Awards programs include Arch Insurance North America, Encova Insurance, Everest Re, Sun Life, Westfield Specialty Insurance, QBE Insurance, American Family Insurance, State Auto, Amerisure, and Neptune Flood. For more information, visit datos-insights.com. ### Media Contact: Walker Sands [email protected]
Mercury, Olympus partner on bundled auto-home coverage in Florida. Mercury Insurance (NYSE: MCY) and Olympus Insurance announced May 7 a joint program that lets independent agents in Florida bundle Mercury auto coverage with qualifying Olympus homeowners policies, with eligible customers receiving a 10% discount on the Mercury auto policy and a 10% discount on the Olympus homeowners policy. The program pairs Mercury, which currently writes auto insurance in Florida, with Olympus, a Florida-focused homeowners carrier that became part of the SageSure family of companies after SageSure closed its acquisition of Gemini Financial Holdings Corp. and the Olympus subsidiaries on Jan. 2. The bundled offering adds another auto-and-home option in
SageSure scales Seawall Re sidecar franchise; secures $200 million in reinsurance. Business Wire Expanded sidecar platform reinforces SageSure's market leadership in bridging institutional capital and high-quality catastrophe risk. JERSEY CITY, N.J., March 10, 2026-(BUSINESS WIRE)-SageSure, the largest residential property MGU in the US specializing in catastrophe-exposed markets and a top global sponsor of catastrophe bonds, today announced the close of its second reinsurance sidecar transaction with Seawall Re II Ltd. ("Seawall Re II"), securing $200 million in capital. In conjunction with its carrier partners, SageSure programs are expected to secure approximately $7 billion of first event reinsurance limit in 2026. Including the debut Seawall Re transaction in July 2025, the SageSure-sponsored sidecar platform has now secured $250 million in less than a year. This rapid expansion underscores SageSure's pioneering role in the convergence of reinsurance capital and capital markets in the catastrophe risk space, a strategic priority as the company continues to mature the insurance-linked securities (ILS) asset class for institutional investors. "SageSure is committed to building long-term investor relationships, and Seawall Re II is a direct reflection of that commitment," said Terrence McLean, President and CEO of SageSure. "We believe that the future of catastrophe risk management lies in the ability to provide investors with a transparent, data-driven gateway to profitable underwriting results. We look forward to continuing to build investor trust with high-quality data, proactive reporting, and sustained outperformance." This transparency facilitates a quota share structure that creates alignment between capital providers, SageSure, and SageSure's underwriting partners SURE, Elevate, SafeChoice, Auros, Interboro, and GeoVera Nova. Carrier partners benefit from incremental catastrophe capacity and reduced net risk positions, while capital providers gain access to a well-priced, well-managed, and diversified catastrophe risk portfolio. GC Securities, a division of MMC Securities LLC, acted as the sole structuring and placement agent for the sidecar transaction. Willkie Farr & Gallagher LLP served as deal counsel. "We're proud to have partnered with SageSure on the Seawall Re platform since its inception," said Liam Martens, Managing Director of GC Securities, a division of MMC Securities LLC. "The strong investor response signals SageSure's differentiated approach to catastrophe risk management is highly attractive to the capital markets. We look forward to building on this momentum as the Seawall Re franchise scales."
People moves: Delos Insurance promotes, hires leadership team members. February 26, 2026 Delos Insurance Solutions made several promotions and appointments within its leadership team Co-founder Shanna McIntyre will move from chief data officer to become chief strategy officer, and Andrew Notohamiprodjo was promoted from head of data to chief data officer. Valencia Jones joins as head of Delos' brokerage distribution from Nationwide where she was associate vice president of sales. Jones is responsible for leading Delos field and internal sales managers and oversees large brokerage and aggregator relationships. Alexandra Howe is Delos' new director of carrier and enterprise relationships. She moves from Goosehead Insurance where she was carrier performance manager. Howe is responsible for leading the growth and performance of Delos' carrier and large account relationships. Lorenzo Houston has joined as compliance manager from SageSure where he was director of personal lines. Delos is headquartered in San Francisco, California. Was this article valuable? Interested in leadership? Get automatic alerts for this topic.
SageSure has entered into a definitive agreement to acquire Gemini Financial and its subsidiaries, including Olympus MGA, the managing general agent for