CareFirst Executive and Leadership Team

November, 2026

Leadership Overview

CareFirst has 10 executives leading key functions including strategy, financial oversight, marketing, operations, and human resources.

Committed to expanding access to quality healthcare, CareFirst delivers specialized Medicare and Medicaid solutions to improve health outcomes for vulnerable populations across Maryland through integrated care management and wellness programs.

Leadership Roles at CareFirst

  • Chief Executive Officer - Michael Felber
  • President & Chief Executive Officer - Kurt Small
  • Chief Financial Officer - Gregory Chaney
  • Executive Vice President & Chief Financial Officer - Ja'Ron Bridges
  • Chief Operating Officer - Cheryl Toland
  • Chief Marketing Officer - Mack McGee
  • Executive Vice President & Chief Marketing Officer - Gregory Devou
  • Executive Vice President & Chief Human Resources Officer - Angela Celestin
  • Executive Assistant To Chief Human Resources Officer - Jackie Burja
  • Executive Vice President & Chief of Staff - Sharon Vecchioni
  • Michael Felber - Chief Executive Officer

    Michael Felber, the Chief Executive Officer at CareFirst, directs the overarching strategic vision for the organization. Felber prioritizes the expansion of Dual Special Needs Plans to ensure comprehensive coverage for Medicare and Medicaid beneficiaries. By aligning corporate objectives with the specific health requirements of Maryland residents, the Chief Executive Officer drives initiatives that simplify access to essential medical services. Michael Felber maintains a focus on long-term sustainability and member-centric care models. This leadership role involves constant evaluation of market trends to refine the Advantage DualPrime plan offerings. Through rigorous oversight of organizational performance, Felber ensures that all departments remain dedicated to the mission of improving community health. The Chief Executive Officer fosters a culture of accountability, enabling the company to meet complex regulatory standards while delivering high-quality care management and transportation services to those requiring additional support.

    Kurt Small - President & Chief Executive Officer

    Kurt Small, the President & Chief Executive Officer at CareFirst, manages the daily operations and high-level execution of the company mission. Small oversees the integration of Original Medicare and Maryland Medicaid benefits to provide seamless coverage for dual-eligible members. As the President & Chief Executive Officer, Small coordinates with internal teams to optimize wellness rewards programs and care management resources. This leadership position requires balancing fiscal responsibility with the delivery of premium-free healthcare solutions. Kurt Small drives the expansion of regional market reach, ensuring that the organization effectively addresses the unique needs of the Maryland population. By fostering partnerships with healthcare providers, the President & Chief Executive Officer strengthens the network of support available to members. Small maintains a commitment to operational excellence, ensuring that every strategic decision directly enhances the quality of life for individuals navigating complex health insurance landscapes.
    Kurt Small

    Gregory Chaney - Chief Financial Officer

    Gregory Chaney, the Chief Financial Officer at CareFirst, manages the fiscal health and capital allocation strategies for the organization. Chaney oversees the financial modeling required to sustain the Advantage DualPrime plan, ensuring that comprehensive benefits remain accessible without monthly premiums. As the Chief Financial Officer, Chaney monitors revenue streams and cost-containment measures to support the long-term viability of Medicare and Medicaid programs. This role involves rigorous analysis of healthcare spending patterns to optimize resource distribution across care management and transportation services. Gregory Chaney collaborates with executive leadership to align financial planning with the broader mission of expanding healthcare access in Maryland. By maintaining strict adherence to regulatory financial standards, the Chief Financial Officer secures the stability necessary for the company to invest in innovative wellness programs. Chaney drives efficiency across all financial departments, ensuring that fiscal performance directly supports the delivery of high-quality member services.

    Ja'Ron Bridges - Executive Vice President & Chief Financial Officer

    Ja'Ron Bridges, the Executive Vice President & Chief Financial Officer at CareFirst, manages the financial architecture and investment strategies of the firm. Bridges oversees the budgeting processes for specialized health programs, ensuring that resources are allocated to maximize the impact of care management and transportation services. As the Executive Vice President & Chief Financial Officer, Bridges evaluates the financial risks associated with the Advantage DualPrime plan to maintain long-term stability. This role involves providing data-driven insights to the Board to support strategic decision-making regarding market expansion and service enhancements. Ja'Ron Bridges drives the implementation of financial controls that ensure compliance with state and federal regulations. By optimizing the capital structure, the Executive Vice President & Chief Financial Officer supports the company's ability to offer premium-free coverage. Bridges maintains a focus on fiscal transparency, ensuring that financial performance remains aligned with the mission of providing high-quality healthcare to the Maryland community.
    Ja'Ron Bridges

    Cheryl Toland - Chief Operating Officer

    Cheryl Toland, the Chief Operating Officer at CareFirst, manages the internal infrastructure and service delivery systems that support member health. Toland oversees the operational workflows for care management and transportation services, ensuring that these programs function efficiently for all beneficiaries. As the Chief Operating Officer, Toland coordinates cross-departmental efforts to maintain high standards of service quality for the Advantage DualPrime plan. This role involves streamlining administrative processes to reduce barriers to care for dual-eligible individuals in Maryland. Cheryl Toland drives the implementation of operational improvements that enhance the member experience and support wellness initiatives. By monitoring performance metrics, the Chief Operating Officer ensures that the organization meets its service level agreements and regulatory requirements. Toland maintains a focus on scalability, allowing the company to adapt its operational capacity to meet the evolving needs of the population while upholding the core mission of accessible, comprehensive healthcare.

    Mack McGee - Chief Marketing Officer

    Mack McGee, the Chief Marketing Officer at CareFirst, directs the brand strategy and member acquisition efforts for the organization. McGee oversees the communication of value propositions related to Dual Special Needs Plans, ensuring that eligible individuals understand the benefits of the Advantage DualPrime plan. As the Chief Marketing Officer, McGee develops targeted outreach campaigns that highlight wellness rewards and care management services. This leadership role involves analyzing market data to identify growth opportunities within the Maryland region. Mack McGee collaborates with product teams to ensure that marketing messaging accurately reflects the comprehensive nature of the coverage provided. By leveraging digital and traditional channels, the Chief Marketing Officer increases awareness of the company's commitment to supporting vulnerable populations. McGee drives engagement through clear, accessible information, ensuring that members feel empowered to manage their health needs effectively through the resources offered by the company.
    Mack McGee

    Gregory Devou - Executive Vice President & Chief Marketing Officer

    Gregory Devou, the Executive Vice President & Chief Marketing Officer at CareFirst, directs the strategic positioning of the company within the competitive insurance landscape. Devou oversees the development of long-term marketing initiatives that emphasize the unique benefits of the Advantage DualPrime plan. As the Executive Vice President & Chief Marketing Officer, Devou analyzes regional market dynamics to refine the outreach strategies for Medicare and Medicaid beneficiaries. This leadership role involves crafting narratives that highlight the company's dedication to wellness rewards and care management. Gregory Devou collaborates with the broader executive team to ensure that marketing efforts align with the overall growth objectives of the organization. By focusing on brand equity and member retention, the Executive Vice President & Chief Marketing Officer strengthens the company's presence in Maryland. Devou drives the creation of educational content that simplifies complex insurance concepts, ensuring that members can easily access and utilize their benefits.

    Angela Celestin - Executive Vice President & Chief Human Resources Officer

    Angela Celestin, the Executive Vice President & Chief Human Resources Officer at CareFirst, directs the talent management and organizational culture initiatives. Celestin oversees the recruitment and development of professionals dedicated to supporting Medicare and Medicaid members. As the Executive Vice President & Chief Human Resources Officer, Celestin implements programs that foster employee engagement and align the workforce with the company's mission of compassionate care. This leadership role involves designing compensation and benefits structures that attract top talent in the insurance industry. Angela Celestin drives the development of training initiatives focused on care management and member support, ensuring that staff possess the skills necessary to serve the Maryland population effectively. By cultivating an inclusive and high-performing environment, the Executive Vice President & Chief Human Resources Officer supports the operational success of the entire organization. Celestin maintains a focus on leadership development, ensuring that the company remains well-positioned to address future healthcare challenges.
    Angela Celestin

    Jackie Burja - Executive Assistant To Chief Human Resources Officer

    Jackie Burja, the Executive Assistant To Chief Human Resources Officer at CareFirst, manages the administrative operations and scheduling for the human resources leadership team. Burja oversees the coordination of executive meetings and facilitates communication between the Chief Human Resources Officer and other departments. As the Executive Assistant To Chief Human Resources Officer, Burja ensures that critical HR initiatives, such as talent acquisition and employee development, receive the necessary administrative support to proceed efficiently. This role involves managing sensitive documentation and maintaining the confidentiality of personnel records. Jackie Burja drives the organization of internal projects that support the company's mission of providing high-quality care to Medicare and Medicaid beneficiaries. By streamlining the workflow for the human resources department, the Executive Assistant To Chief Human Resources Officer enables the leadership team to focus on strategic workforce planning. Burja maintains a high level of operational readiness, ensuring that the HR function remains responsive to the needs of the organization.

    Sharon Vecchioni - Executive Vice President & Chief of Staff

    Sharon Vecchioni, the Executive Vice President & Chief of Staff at CareFirst, manages the strategic alignment of executive priorities and organizational goals. Vecchioni oversees the execution of cross-functional projects that integrate care management and wellness programs across the company. As the Executive Vice President & Chief of Staff, Vecchioni facilitates communication between the CEO and other C-suite leaders to ensure a unified approach to market challenges. This role involves monitoring the progress of key initiatives related to the Advantage DualPrime plan and providing actionable insights to the leadership team. Sharon Vecchioni drives the implementation of governance processes that enhance decision-making efficiency. By coordinating the efforts of various departments, the Executive Vice President & Chief of Staff ensures that the organization remains focused on its mission of serving dual-eligible individuals in Maryland. Vecchioni maintains a comprehensive view of operations, enabling the company to respond rapidly to changes in the healthcare landscape while upholding high standards of service.

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    Frequently Asked Questions Regarding CareFirst Top Executives and Leadership Team

    Who leads CareFirst?
    CareFirst is led by Michael Felber (Chief Executive Officer), along with executives such as Kurt Small (President & Chief Executive Officer) and Gregory Chaney (Chief Financial Officer).
    Who is part of CareFirst’s executive team?
    The executive team of CareFirst includes leaders such as Michael Felber (Chief Executive Officer), Kurt Small (President & Chief Executive Officer), Gregory Chaney (Chief Financial Officer) and other senior executives.
    How many executives does CareFirst have?
    CareFirst has 10 executives leading key business areas.
    What roles are included in CareFirst’s leadership team?
    The leadership team of CareFirst includes roles such as Chief Executive Officer, President & Chief Executive Officer, Chief Financial Officer, Executive Vice President & Chief Financial Officer, Chief Operating Officer.