Cross Insurance Executive and Leadership Team

July, 2026

Leadership Overview

Cross Insurance has 8 executives leading key functions including strategy, finance, operations, and regional management.

Driven by a commitment to client success, Cross Insurance provides comprehensive personal and commercial insurance solutions, leveraging decades of industry expertise to deliver tailored protection and exceptional service across diverse markets.

Leadership Roles at Cross Insurance

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

    Jonathan Cross, the Chief Executive Officer at Cross Insurance, directs the overarching corporate strategy and long-term vision. Overseeing all major business units, Jonathan Cross ensures alignment with market demands and client needs, driving growth initiatives across the organization. This leadership role involves fostering a culture of innovation and client-centricity, essential for maintaining Cross Insurance's position as an independent insurance intermediary. By guiding executive decision-making, Jonathan Cross impacts the company's operational efficiency and financial performance, securing its market presence in personal and commercial insurance sectors.

    Bruce Nickerson - Chief Financial Officer

    Bruce Nickerson, the Chief Financial Officer at Cross Insurance, manages all financial operations and fiscal strategy. Overseeing budgeting, forecasting, and financial reporting, Bruce Nickerson ensures the company's fiscal health and sustainable growth. This critical role involves managing investment strategies and capital allocation to support Cross Insurance's expansion and operational objectives. By maintaining robust financial controls and compliance, Bruce Nickerson directly influences the company's profitability and market competitiveness, safeguarding assets and optimizing resource utilization for the insurance intermediary.
    Bruce Nickerson

    Francis Ferland - Chief Operating Officer

    Francis Ferland, the Chief Operating Officer at Cross Insurance, oversees the day-to-day operational execution and efficiency across all departments. Francis Ferland directs the implementation of strategic initiatives, ensuring seamless service delivery for both personal and commercial insurance clients. This position involves optimizing internal processes, managing resource allocation, and driving operational excellence to enhance client satisfaction and retention. By streamlining workflows and fostering cross-functional collaboration, Francis Ferland directly contributes to the company's ability to provide comprehensive insurance solutions and maintain its competitive edge in the market.

    David Messersmith - President, Cross Insurance Coastal Region

    David Messersmith, the President, Cross Insurance Coastal Region at Cross Insurance, leads all operations and strategic development within the coastal territories. Overseeing regional sales, client relations, and market expansion, David Messersmith ensures tailored insurance solutions meet the specific needs of businesses and individuals in these areas. This executive role involves cultivating strong broker partnerships and driving revenue growth through localized market penetration. By focusing on regional expertise and client service, David Messersmith directly enhances Cross Insurance's presence and impact along the coast.
    David Messersmith

    Gary Heaslip - President

    Gary Heaslip, the President at Cross Insurance, drives strategic initiatives and operational oversight for designated business segments. Overseeing key functional areas, Gary Heaslip ensures the effective execution of company policies and client service standards. This leadership position involves fostering strong relationships with clients and partners, contributing to the overall growth and success of the insurance intermediary. By focusing on operational excellence and market responsiveness, Gary Heaslip directly supports Cross Insurance's mission to provide comprehensive personal and commercial insurance.

    Eric Jermyn - President, Employee Benefits

    Eric Jermyn, the President, Employee Benefits at Cross Insurance, directs the strategic vision and operational execution for the employee benefits division. Overseeing the development and delivery of comprehensive benefits programs, Eric Jermyn ensures clients receive tailored solutions that meet their workforce needs. This role involves managing client relationships, driving sales growth, and maintaining compliance with evolving regulations in the employee benefits landscape. By focusing on specialized expertise, Eric Jermyn directly enhances Cross Insurance's capacity to serve businesses seeking robust employee benefit packages.

    Robert Wade - President

    Robert Wade, the President at Cross Insurance, spearheads strategic growth and operational management for key market segments. Overseeing business development and client acquisition efforts, Robert Wade ensures the effective delivery of personal and commercial insurance products. This executive function involves cultivating strategic partnerships and driving revenue expansion through market penetration. By focusing on client needs and service excellence, Robert Wade directly contributes to Cross Insurance's reputation as a leading independent insurance intermediary.

    Christopher Sharpe - President

    Christopher Sharpe, the President at Cross Insurance, leads strategic planning and operational execution for assigned business units. Overseeing client engagement and service delivery, Christopher Sharpe ensures adherence to the company's core values of integrity and expertise. This leadership role involves driving market share growth and fostering strong relationships within the insurance sector. By focusing on operational efficiency and client satisfaction, Christopher Sharpe directly supports Cross Insurance's commitment to providing comprehensive insurance solutions.
    Christopher Sharpe

    Explore Leadership Teams in Insurance

    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 Bruce Nickerson (Chief Financial Officer) and Francis Ferland (Chief Operating Officer).
    Who is part of Cross Insurance’s executive team?
    The executive team of Cross Insurance includes leaders such as Jonathan Cross (Chief Executive Officer), Bruce Nickerson (Chief Financial Officer), Francis Ferland (Chief Operating Officer) and other senior executives.
    How many executives does Cross Insurance have?
    Cross Insurance has 8 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 Financial Officer, Chief Operating Officer, President, Cross Insurance Coastal Region, President.