Sunstar Insurance Group Executive and Leadership Team

September, 2026

Leadership Overview

Sunstar Insurance Group has 6 executives leading key functions including strategy, financial oversight, operational scaling, and administrative management.

Focused on acquiring independent insurance agencies, Sunstar Insurance Group delivers robust brokerage resources while maintaining local responsiveness across its extensive network of 75 offices and $1.5 billion in written premiums.

Leadership Roles at Sunstar Insurance Group

  • Chief Executive Officer - Jason Swindle
  • President & Chief Executive Officer - Robert Fiss
  • Executive Vice President & Chief Financial Officer - Christopher Parcell
  • President & Chief Operating Officer - Gregory Lottes
  • Chief Administrative Officer - Gail Boland
  • Chief Administrative Officer (CAO) - Lee Madonna
  • Jason Swindle - Chief Executive Officer

    Jason Swindle, the Chief Executive Officer at Sunstar Insurance Group, directs the overarching corporate strategy and acquisition roadmap for the organization. Swindle manages the integration of independent insurance agencies into the broader holding company structure, ensuring that each partner maintains operational agility while gaining access to enterprise-level resources. By overseeing the expansion across 8 states, the Chief Executive Officer drives the growth of the $1.5 billion premium portfolio. This leadership role involves constant collaboration with the Board to identify new market opportunities within the commercial lines and employee benefits sectors. Jason Swindle prioritizes the alignment of agency partners with the core mission of providing superior insurance solutions. Through rigorous oversight of the acquisition pipeline, the Chief Executive Officer secures the long-term financial health of the group. Swindle maintains a focus on scaling the business model to support the evolving needs of agency partners throughout the regional footprint.
    Jason Swindle

    Robert Fiss - President & Chief Executive Officer

    Robert Fiss, the President & Chief Executive Officer at Sunstar Insurance Group, leads the executive team in executing the long-term vision for the financial holding company. Fiss manages the high-level relationships with agency partners, ensuring that the group provides the necessary expertise to compete effectively in the insurance market. Overseeing the strategic direction of the 800-employee organization, the President & Chief Executive Officer ensures that all business units remain focused on delivering high-quality commercial lines and surety bonds. Robert Fiss coordinates with other C-suite leaders to optimize the performance of the 75 offices currently under the corporate umbrella. This role involves balancing the needs of independent agencies with the requirements of a large-scale brokerage. By fostering a culture of excellence, the President & Chief Executive Officer drives consistent revenue growth. Fiss maintains a commitment to the group's mission of providing institutional-grade support to local insurance agencies.

    Christopher Parcell - Executive Vice President & Chief Financial Officer

    Christopher Parcell, the Executive Vice President & Chief Financial Officer at Sunstar Insurance Group, manages the financial architecture and capital allocation strategies for the entire organization. Parcell oversees the fiscal health of the 75 offices, ensuring that the $1.5 billion in written premiums remains stable and profitable. By directing the financial reporting and budgeting processes, the Executive Vice President & Chief Financial Officer provides the data necessary for informed acquisition decisions. Christopher Parcell collaborates with the leadership team to evaluate the financial viability of potential agency partners within the 8-state footprint. This role involves managing the complex balance sheet requirements of a financial holding company while supporting the growth of commercial lines and employee benefits. Through meticulous oversight of capital resources, the Executive Vice President & Chief Financial Officer ensures that the group maintains the strength of a publicly traded brokerage. Parcell drives the financial discipline required to sustain long-term market impact.
    Christopher Parcell

    Gregory Lottes - President & Chief Operating Officer

    Gregory Lottes, the President & Chief Operating Officer at Sunstar Insurance Group, directs the daily operational workflows and service delivery standards across the company's 75 offices. Lottes manages the integration of operational systems to ensure that all 800 employees and partners function with maximum efficiency. By overseeing the implementation of standardized processes for personal lines and surety bonds, the President & Chief Operating Officer ensures that the group maintains its reputation for responsiveness. Gregory Lottes coordinates with regional managers to streamline the delivery of brokerage resources to agency partners. This leadership role involves optimizing the operational infrastructure to support the company's expansion across 8 states. Through the continuous improvement of internal procedures, the President & Chief Operating Officer drives the scalability of the business model. Lottes ensures that the operational framework remains aligned with the overarching mission of providing high-quality insurance services to the diverse client base.
    Gregory Lottes

    Gail Boland - Chief Administrative Officer

    Gail Boland, the Chief Administrative Officer at Sunstar Insurance Group, directs the internal administrative functions and organizational support systems that sustain the company's 800 employees. Boland manages the human resources strategy, corporate compliance, and internal communications to ensure that the 75 offices operate in alignment with company policies. By overseeing the administrative infrastructure, the Chief Administrative Officer ensures that the group maintains a cohesive culture across its 8-state footprint. Gail Boland collaborates with the executive team to implement policies that support the acquisition of independent insurance agencies. This role involves managing the organizational design to facilitate the growth of commercial lines and employee benefits services. Through the optimization of administrative processes, the Chief Administrative Officer drives operational efficiency and employee engagement. Boland ensures that the internal support systems remain robust enough to handle the complexities of a large-scale financial holding company while maintaining the agility of a local agency partner.

    Lee Madonna - Chief Administrative Officer (CAO)

    Lee Madonna, the Chief Administrative Officer (CAO) at Sunstar Insurance Group, directs the strategic management of corporate facilities and technology infrastructure. Madonna manages the integration of new agency partners into the company's centralized administrative systems, ensuring seamless transitions for all 75 offices. By overseeing the technological and physical assets of the group, the Chief Administrative Officer (CAO) ensures that the organization maintains the capacity to handle $1.5 billion in written premiums. Lee Madonna collaborates with the leadership team to identify opportunities for administrative consolidation and cost-saving measures across the 8-state footprint. This role involves managing the vendor relationships and service contracts that support the daily operations of the insurance brokerage. Through the modernization of administrative tools, the Chief Administrative Officer (CAO) drives the efficiency of the entire organization. Madonna ensures that the administrative framework supports the company's mission of providing superior resources to its agency partners.
    Lee Madonna

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    Frequently Asked Questions Regarding Sunstar Insurance Group Top Executives and Leadership Team

    Who leads Sunstar Insurance Group?
    Sunstar Insurance Group is led by Jason Swindle (Chief Executive Officer), along with executives such as Robert Fiss (President & Chief Executive Officer) and Christopher Parcell (Executive Vice President & Chief Financial Officer).
    Who is part of Sunstar Insurance Group’s executive team?
    The executive team of Sunstar Insurance Group includes leaders such as Jason Swindle (Chief Executive Officer), Robert Fiss (President & Chief Executive Officer), Christopher Parcell (Executive Vice President & Chief Financial Officer) and other senior executives.
    How many executives does Sunstar Insurance Group have?
    Sunstar Insurance Group has 6 executives leading key business areas.
    What roles are included in Sunstar Insurance Group’s leadership team?
    The leadership team of Sunstar Insurance Group includes roles such as Chief Executive Officer, President & Chief Executive Officer, Executive Vice President & Chief Financial Officer, President & Chief Operating Officer, Chief Administrative Officer.