Director of Alternative Capacity Finance and Operations

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Director / Senior Manager – Alternative Capacity Finance & Operations

Reciprocal, Sidecar & Alternative Capacity Vehicles

Position Summary

We are seeking an experienced insurance professional to lead financial and operational oversight across a reciprocal exchange, sidecars, and alternative capacity vehicles. This is a high-impact role for a leader who can bring structure, discipline, and transparency to complex risk-bearing platforms by establishing strong governance, effective controls, and clear operating frameworks while also helping business leaders better understand performance, risk, and opportunities across the portfolio.

The ideal candidate brings deep experience in insurance financial operations, delegated authority environments, and alternative risk transfer structures, along with the judgment to identify risk, strengthen oversight, and translate data into actionable insights. This individual will play a key role in enhancing financial integrity, driving performance transparency, and building scalable control frameworks that not only support disciplined execution, but also improve decision-making, operational efficiency, and long-term value creation across multiple capacity platforms.

Key Responsibilities

Governance, Controls & Compliance

• Design and implement governance frameworks and operational oversight processes that strengthen control, improve transparency, and support scalable execution across insurance capacity vehicles
• Establish and monitor key controls related to delegated authority, financial reporting, and operational execution, while using those controls to surface trends, exceptions, and opportunities for improvement
• Partner with legal, compliance, and regulatory teams to ensure adherence to regulatory, contractual, and reporting requirements
• Coordinate audits, regulatory examinations, and third-party reviews
• Oversee service-level agreements (SLAs) and delegated authority standards, ensuring compliance while improving partner performance, accountability, and operating consistency
• Identify operational risks and drive mitigation strategies, process improvements, and control enhancements that reduce friction and strengthen business performance

Financial & Operational Oversight

• Lead oversight of financial operations across reciprocal exchanges, sidecars, captives, and alternative capacity vehicles, ensuring disciplined execution and clear visibility into performance drivers
• Monitor key financial and operational metrics, including:
  • Premium flow and revenue recognition
  • Loss activity and reserve development
  • Reinsurance settlements and recoverables
  • Collateral and trust account balances
  • Expense allocations and profitability
• Partner with accounting and finance teams to support monthly, quarterly, and annual close processes
• Review and validate bordereaux, underwriting performance data, and program-level KPIs to identify emerging issues, improve reporting quality, and support timely decision-making
• Develop and maintain reporting packages for senior leadership that translate financial and operational data into clear insights on performance, risk, and value creation opportunities
• Oversee cash management processes, including trust account monitoring and reconciliations
• Ensure operational alignment across MGAs, carriers, TPAs, reinsurers, and third-party administrators to strengthen execution, improve information flow, and support consistent performance

Strategic & Cross-Functional Leadership

• Partner with underwriting, actuarial, and finance leadership to evaluate portfolio performance, capital efficiency, and operational drivers that influence profitability and growth
• Support onboarding and implementation of new programs, capacity structures, and strategic partnerships
• Contribute to strategic planning related to alternative capital deployment and insurance program expansion by bringing a disciplined perspective on governance, operating readiness, and value creation
• Provide financial and operational insights that help executive leadership assess performance, prioritize actions, and make informed strategic decisions
• Lead or support initiatives focused on:
  • Process automation
  • Reporting enhancements
  • Operational scalability

Qualifications

• Bachelor’s degree in Finance, Accounting, Business Administration, Risk Management, Insurance, or related field
• 5+ years of experience in insurance, reinsurance, delegated authority, program business, or alternative risk environments, ideally within a carrier, MGA, reciprocal exchange, or related specialty platform
• Strong understanding of:
  • Insurance operations and delegated authority models
  • Reinsurance structures and settlements
  • Alternative capital vehicles (sidecars, captives, fronting, third-party capital)
• Experience in financial operations, reporting, reconciliations, and governance oversight, with the ability to translate complex data into clear insights and actionable recommendations
• Working knowledge of statutory accounting principles and insurance financial reporting
• Proven ability to operate cross-functionally across finance, underwriting, actuarial, compliance, and external stakeholders, influencing decisions and driving alignment in complex operating environments
• Strong analytical, organizational, and project management capabilities, with sound judgment and a demonstrated ability to identify issues, prioritize actions, and improve performance
• Advanced Excel and financial reporting tool proficiency, with the ability to build reporting and analysis that improve transparency and support decision-making

Preferred Experience

• Experience with program business or specialty insurance operations, including environments where financial discipline, performance visibility, and operating consistency are critical
• Exposure to alternative capital markets, ILS structures, or strategic reinsurance arrangements, with an understanding of how those structures influence governance, profitability, and growth
• Track record of building governance frameworks or implementing operational control environments that improve transparency, accountability, and business performance
• CPA, MBA, CPCU, ARe, or similar designation that strengthens financial, strategic, or industry expertise

What Will Make You Successful

• You bring strong financial and operational judgment, with the ability to identify risk, evaluate performance, and focus attention on the issues that matter most
• You are comfortable operating in complex insurance or risk environments where strong governance, disciplined execution, and transparency are essential
• You can translate detailed financial and operational data into clear insights, practical recommendations, and actions that improve business performance
• You work effectively across finance, underwriting, actuarial, compliance, and external partners, building alignment and driving accountability in cross-functional settings
• You are effective at building structure in evolving environments, strengthening processes and controls while supporting scalability and growth
• You balance attention to detail with strategic perspective, moving comfortably between day-to-day oversight and broader business priorities
• You communicate with clarity and credibility, enabling leaders and stakeholders to make informed decisions with confidence

Reporting Structure

This role reports into senior leadership within Finance, and works closely with underwriting, actuarial, legal, compliance, claims, and external capacity partners.

Why Join Us

This is a distinctive opportunity to help shape the governance, operating discipline, and performance visibility of innovative insurance capacity platforms in a market that continues to evolve. The role offers meaningful exposure to senior leadership and a chance to influence how reciprocal, sidecar, and alternative capacity structures are managed, scaled, and strengthened over time.

For the right candidate, this role combines rigorous financial and operational oversight with the opportunity to generate insight, improve execution, and create long-term business value. It is well suited for a leader who wants to bring structure to complex environments, partner across functions, and have a direct hand in strengthening platforms that are strategically important to the business.