Starwind Specialty Insurance Executive and Leadership Team

September, 2026

Leadership Overview

Starwind Specialty Insurance has 5 executives leading key functions including program management, property catastrophe underwriting, and environmental insurance solutions.

Focused on delivering robust insurance intelligence, Starwind Specialty Insurance empowers clients through accessible digital tools and tailored risk management programs designed for diverse business requirements.

Leadership Roles at Starwind Specialty Insurance

  • President, Program - Carolyn Toomey
  • President, Program - Brian Elliott
  • President, Starwind Property Cat - Thomas Olcott
  • President, Program - Christopher Kirby
  • President, Program, Environmental - Michael Padula
  • Carolyn Toomey - President, Program

    Carolyn Toomey, the President, Program at Starwind Specialty Insurance, directs the strategic development of specialized insurance programs. Overseeing the expansion of underwriting capabilities, Toomey ensures the alignment of product offerings with evolving market demands. This leadership role involves managing complex risk portfolios while maintaining high standards of service accessibility. By optimizing the digital platform, Carolyn Toomey drives operational efficiency across North American markets. Toomey coordinates with internal teams to refine quote management tools, ensuring clients receive precise insurance solutions. Through rigorous analysis of industry trends, Toomey secures competitive advantages for the organization. The President, Program maintains a focus on sustainable growth, fostering long-term relationships with brokers and policyholders. By prioritizing data-driven decision-making, Toomey enhances the overall value proposition of the company, ensuring that every insurance program meets the diverse needs of modern businesses seeking reliable coverage options.
    Carolyn Toomey

    Brian Elliott - President, Program

    Brian Elliott, the President, Program at Starwind Specialty Insurance, manages the operational execution of core insurance initiatives. Focusing on the scalability of program distribution, Elliott architects frameworks that simplify the client experience. This leadership role requires constant collaboration with technical teams to improve the functionality of the online insurance portal. Brian Elliott drives the implementation of new underwriting guidelines, ensuring compliance and profitability across all regional operations. By streamlining the quote acquisition process, Elliott reduces friction for businesses navigating complex insurance landscapes. The President, Program monitors performance metrics to identify opportunities for service enhancement. Through strategic oversight of program lifecycles, Elliott maintains the integrity of the company's insurance offerings. By fostering a culture of precision and responsiveness, Elliott ensures that the organization remains a leader in providing valuable resources and intelligence to clients seeking comprehensive protection for various commercial risks.

    Thomas Olcott - President, Starwind Property Cat

    Thomas Olcott, the President, Starwind Property Cat at Starwind Specialty Insurance, oversees the specialized property catastrophe division. Directing the assessment of high-exposure risks, Olcott ensures the stability of the company's property insurance portfolio. This leadership role involves analyzing complex data sets to model potential loss scenarios, providing critical intelligence for underwriting decisions. Thomas Olcott drives the development of catastrophe-focused insurance products that address the specific needs of clients in vulnerable regions. By coordinating with global reinsurance partners, Olcott manages risk capacity and ensures financial resilience. The President, Starwind Property Cat maintains a rigorous focus on market volatility, adjusting strategies to protect the organization against large-scale events. Through the application of advanced analytics, Olcott enhances the accuracy of pricing models. By leading the property catastrophe team, Olcott secures the company's position as a reliable provider of essential coverage for businesses facing significant environmental and structural risks.

    Christopher Kirby - President, Program

    Christopher Kirby, the President, Program at Starwind Specialty Insurance, manages the strategic growth of diverse insurance programs. Overseeing the integration of new market segments, Kirby ensures that the company's offerings remain relevant to changing business requirements. This leadership role involves identifying emerging risks and designing tailored insurance solutions to address those gaps. Christopher Kirby drives the expansion of the company's footprint by optimizing distribution channels and enhancing broker engagement. By leveraging the online platform, Kirby improves the accessibility of insurance tools for a broad client base. The President, Program collaborates with cross-functional teams to refine service delivery, ensuring that every program provides maximum value. Through consistent monitoring of market performance, Kirby adjusts operational tactics to maintain a competitive edge. By focusing on innovation and client-centric design, Kirby ensures that the organization continues to provide high-quality insurance resources that support the diverse needs of individuals and businesses.

    Michael Padula - President, Program, Environmental

    Michael Padula, the President, Program, Environmental at Starwind Specialty Insurance, directs the specialized environmental insurance division. Overseeing the underwriting of complex pollution and environmental liability risks, Padula ensures that the company provides robust protection for industrial and commercial clients. This leadership role involves navigating intricate regulatory landscapes to design compliant insurance programs. Michael Padula drives the development of risk management tools that assist clients in identifying and mitigating environmental hazards. By collaborating with technical experts, Padula enhances the precision of environmental risk assessments. The President, Program, Environmental monitors industry shifts to ensure that the company's coverage remains aligned with evolving environmental standards. Through strategic outreach, Padula expands the reach of environmental insurance solutions across various sectors. By maintaining a focus on specialized expertise, Padula secures the organization's reputation as a trusted partner for businesses managing significant environmental exposures and seeking comprehensive insurance solutions.

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    Frequently Asked Questions Regarding Starwind Specialty Insurance Top Executives and Leadership Team

    Who leads Starwind Specialty Insurance?
    Starwind Specialty Insurance is led by Carolyn Toomey (President, Program), along with executives such as Brian Elliott (President, Program) and Thomas Olcott (President, Starwind Property Cat).
    Who is part of Starwind Specialty Insurance’s executive team?
    The executive team of Starwind Specialty Insurance includes leaders such as Carolyn Toomey (President, Program), Brian Elliott (President, Program), Thomas Olcott (President, Starwind Property Cat) and other senior executives.
    How many executives does Starwind Specialty Insurance have?
    Starwind Specialty Insurance has 5 executives leading key business areas.
    What roles are included in Starwind Specialty Insurance’s leadership team?
    The leadership team of Starwind Specialty Insurance includes roles such as President, Program, President, Program, President, Starwind Property Cat, President, Program, President, Program, Environmental.