Cross Insurance Executive and Leadership Team

October, 2026

Leadership Overview

Cross Insurance has 6 executives leading key functions including strategy, operations, regional management, and employee benefits.

Committed to providing comprehensive coverage solutions, Cross Insurance maintains a legacy of independent brokerage excellence while driving innovation across personal and commercial insurance markets to ensure client security.

Leadership Roles at Cross Insurance

  • Chief Executive Officer - Jonathan Cross
  • Chief Operating Officer - Francis Ferland
  • President - Gary Heaslip
  • President, Employee Benefits - Eric Jermyn
  • President - Robert Wade
  • President, Cross Insurance Coastal Region - David Messersmith
  • Jonathan Cross - Chief Executive Officer

    Jonathan Cross, the Chief Executive Officer at Cross Insurance, directs the overarching strategic vision for the organization. Overseeing long-term growth initiatives, the Chief Executive Officer ensures the firm maintains a competitive edge as an independent insurance intermediary. This leadership role involves managing relationships with key stakeholders and guiding the executive team toward sustainable expansion. By prioritizing client-centric service models, Jonathan Cross directly influences the company's market reputation. The Chief Executive Officer monitors industry trends to adapt service offerings for personal and commercial clients. Through rigorous oversight of corporate governance, Cross fosters a culture of excellence. This executive leadership supports the firm's mission to provide robust protection across diverse sectors. Ultimately, the Chief Executive Officer secures the financial health and operational integrity of the entire enterprise while navigating complex regulatory landscapes within the insurance industry.

    Francis Ferland - Chief Operating Officer

    Francis Ferland, the Chief Operating Officer at Cross Insurance, manages the daily operational workflows and internal infrastructure. Overseeing the integration of technology and administrative processes, the Chief Operating Officer ensures maximum efficiency across all departments. This leadership role involves streamlining service delivery for personal and commercial insurance products. By optimizing internal systems, Francis Ferland directly impacts the firm's ability to scale operations effectively. The Chief Operating Officer coordinates with department heads to align resource allocation with corporate objectives. Through meticulous management of operational risks, Ferland maintains high standards of service quality. This executive function supports the company's commitment to reliable insurance brokerage. Ultimately, the Chief Operating Officer drives the internal performance metrics necessary to sustain growth and operational excellence within the competitive insurance landscape, ensuring that all business units function in perfect harmony.

    Gary Heaslip - President

    Gary Heaslip, the President at Cross Insurance, directs commercial insurance growth and market expansion strategies. Overseeing the development of specialized coverage programs, the President ensures the firm meets the complex needs of commercial clients. This leadership role involves driving revenue through strategic partnerships and client acquisition efforts. By focusing on market penetration, Gary Heaslip directly influences the company's commercial portfolio performance. The President collaborates with the executive team to refine service offerings and enhance competitive positioning. Through active management of commercial accounts, Heaslip maintains strong client retention rates. This executive function supports the firm's mission to provide comprehensive insurance solutions. Ultimately, the President secures the commercial division's market share and profitability, ensuring that the organization remains a leader in providing tailored insurance products to businesses across the region while maintaining high standards of professional service.

    Eric Jermyn - President, Employee Benefits

    Eric Jermyn, the President, Employee Benefits at Cross Insurance, manages the specialized division focused on group health and welfare programs. Overseeing the design and implementation of benefit packages, the President, Employee Benefits ensures clients receive competitive and compliant solutions. This leadership role involves navigating the complexities of the employee benefits market to provide value-added services. By driving innovation in benefit administration, Eric Jermyn directly impacts the firm's ability to attract and retain corporate clients. The President, Employee Benefits coordinates with carriers and consultants to optimize plan performance. Through strategic oversight of this division, Jermyn maintains the firm's reputation for excellence in human capital risk management. This executive function supports the company's broader mission to provide holistic insurance coverage. Ultimately, the President, Employee Benefits secures the division's growth and client satisfaction through expert guidance and proactive service delivery.

    Robert Wade - President

    Robert Wade, the President at Cross Insurance, directs personal insurance operations and client service excellence. Overseeing the management of individual policy portfolios, the President ensures the firm delivers high-quality coverage to personal lines clients. This leadership role involves refining the customer experience and enhancing service accessibility. By focusing on personal insurance growth, Robert Wade directly influences the company's stability and client loyalty. The President collaborates with regional teams to ensure consistent service delivery across all personal insurance segments. Through rigorous oversight of policy management, Wade maintains the firm's commitment to protecting individual assets. This executive function supports the company's mission to provide reliable insurance brokerage services. Ultimately, the President secures the personal lines division's market position through dedicated leadership and a focus on meeting the evolving needs of individual policyholders, ensuring that every client receives personalized attention and comprehensive coverage solutions.

    David Messersmith - President, Cross Insurance Coastal Region

    David Messersmith, the President, Cross Insurance Coastal Region at Cross Insurance, directs all operations and business development within the coastal market territory. Overseeing regional growth strategies, the President, Cross Insurance Coastal Region ensures the firm captures market opportunities in this specific geographic area. This leadership role involves managing local client relationships and adapting service models to regional insurance requirements. By driving regional performance, David Messersmith directly impacts the company's overall market reach. The President, Cross Insurance Coastal Region coordinates with corporate leadership to align regional activities with the broader organizational mission. Through active engagement with local business communities, Messersmith strengthens the firm's presence. This executive function supports the company's commitment to providing localized insurance expertise. Ultimately, the President, Cross Insurance Coastal Region secures the firm's competitive advantage in the coastal market through strategic oversight and dedicated regional management.
    David Messersmith

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    Frequently Asked Questions Regarding Cross Insurance Top Executives and Leadership Team

    Who leads Cross Insurance?
    Cross Insurance is led by Jonathan Cross (Chief Executive Officer), along with executives such as Francis Ferland (Chief Operating Officer) and Gary Heaslip (President).
    Who is part of Cross Insurance’s executive team?
    The executive team of Cross Insurance includes leaders such as Jonathan Cross (Chief Executive Officer), Francis Ferland (Chief Operating Officer), Gary Heaslip (President) and other senior executives.
    How many executives does Cross Insurance have?
    Cross Insurance has 6 executives leading key business areas.
    What roles are included in Cross Insurance’s leadership team?
    The leadership team of Cross Insurance includes roles such as Chief Executive Officer, Chief Operating Officer, President, President, Employee Benefits, President.