GuideWell Executive and Leadership Team

September, 2026

Leadership Overview

GuideWell has 7 executives leading key functions including strategy, technology, financial oversight, information systems, executive operations, communications, and health care services.

Focused on delivering integrated healthcare solutions across North America, GuideWell prioritizes elderly care through advanced digital platforms and comprehensive insurance coverage to improve patient outcomes.

Leadership Roles at GuideWell

  • President & Chief Executive Officer - Brian Pieninck
  • Chief of Staff To the Office of the Chief Executive Officer - Courtney Harris
  • Chief Financial Officer, Government Business - David Petruzzellis
  • Senior VP, Health Care Services & President, Guidewell Health - Elana Schrader
  • Chief Technology Officer - Robert Ruocco
  • Senior Vice President, Chief Information Officer - Gary Anderson
  • Chief Communications Officer - Farley Kern
  • Brian Pieninck - President & Chief Executive Officer

    Brian Pieninck, the President & Chief Executive Officer at GuideWell, directs the overarching strategic vision for the organization. Overseeing the expansion of integrated health care solutions, the President & Chief Executive Officer ensures alignment between corporate objectives and the evolving needs of the elderly population. This leadership role involves managing complex business-to-business and direct-to-consumer healthcare initiatives across North American markets. By fostering innovation within the digital platform ecosystem, Brian Pieninck drives sustainable growth and operational excellence. The President & Chief Executive Officer maintains constant collaboration with the Board to refine long-term goals. Through rigorous oversight of health insurance plans and specialized medical care programs, the President & Chief Executive Officer secures the company's market position. Ultimately, the President & Chief Executive Officer champions a culture of service, ensuring that every technological advancement directly benefits the health outcomes of the diverse member base.
    Brian Pieninck

    Courtney Harris - Chief of Staff To the Office of the Chief Executive Officer

    Courtney Harris, the Chief of Staff To the Office of the Chief Executive Officer at GuideWell, coordinates the strategic priorities and daily operations of the executive office. Overseeing the flow of information between departments, the Chief of Staff To the Office of the Chief Executive Officer ensures that corporate initiatives remain aligned with the mission of providing integrated healthcare. This leadership role involves facilitating communication across the organization to drive cross-functional collaboration. By managing high-level projects and executive meetings, Courtney Harris optimizes the productivity of the leadership team. The Chief of Staff To the Office of the Chief Executive Officer works closely with the President to execute key business strategies across North America. Through the synthesis of complex operational data, the Chief of Staff To the Office of the Chief Executive Officer supports informed decision-making at the highest level. Ultimately, the Chief of Staff To the Office of the Chief Executive Officer maintains organizational focus, ensuring that all teams remain dedicated to the company's core healthcare objectives.

    David Petruzzellis - Chief Financial Officer, Government Business

    David Petruzzellis, the Chief Financial Officer, Government Business at GuideWell, manages the fiscal health and budgetary planning for government-contracted healthcare services. Overseeing financial reporting and resource allocation, the Chief Financial Officer, Government Business ensures compliance with regulatory standards while maximizing the impact of health insurance plans. This leadership role involves analyzing market trends to support the expansion of specialized medical care programs. By maintaining rigorous financial discipline, David Petruzzellis drives the economic viability of the company's North American operations. The Chief Financial Officer, Government Business works closely with the executive team to align fiscal strategies with the broader mission of providing comprehensive care. Through precise financial modeling and risk assessment, the Chief Financial Officer, Government Business secures the necessary capital to invest in future service offerings. Ultimately, the Chief Financial Officer, Government Business guarantees the long-term financial stability required to sustain high-quality healthcare delivery for the elderly.

    Elana Schrader - Senior VP, Health Care Services & President, Guidewell Health

    Elana Schrader, the Senior VP, Health Care Services & President, Guidewell Health at GuideWell, manages the delivery of clinical services and the operational performance of the health division. Overseeing the implementation of specialized medical care programs, the Senior VP, Health Care Services & President, Guidewell Health ensures that patient-centered solutions meet the highest standards of quality. This leadership role involves driving the expansion of health services across North American markets to better serve the elderly population. By optimizing clinical workflows, Elana Schrader improves the efficiency and effectiveness of healthcare delivery. The Senior VP, Health Care Services & President, Guidewell Health works with the executive team to integrate medical care with insurance and retirement planning offerings. Through the oversight of health service operations, the Senior VP, Health Care Services & President, Guidewell Health supports the company's mission to provide comprehensive, integrated care. Ultimately, the Senior VP, Health Care Services & President, Guidewell Health ensures that clinical excellence remains the foundation of the company's healthcare services.

    Robert Ruocco - Chief Technology Officer

    Robert Ruocco, the Chief Technology Officer at GuideWell, architects the advanced technology infrastructure supporting all healthcare service delivery. Overseeing the development of mobile applications and digital health platforms, the Chief Technology Officer ensures seamless integration of vision, dental, and retirement planning tools. This leadership role involves managing the technical roadmap to enhance user experience for direct-to-consumer healthcare solutions. By optimizing data security and system scalability, Robert Ruocco directly impacts the efficiency of medical care programs. The Chief Technology Officer collaborates with executive leadership to implement cutting-edge software solutions that streamline administrative processes. Through the deployment of robust digital frameworks, the Chief Technology Officer supports the company's mission to provide accessible care across North America. Ultimately, the Chief Technology Officer maintains the integrity of the technological ecosystem, ensuring that all digital touchpoints remain reliable, secure, and highly responsive to the needs of the elderly population.
    Robert Ruocco

    Gary Anderson - Senior Vice President, Chief Information Officer

    Gary Anderson, the Senior Vice President, Chief Information Officer at GuideWell, directs the enterprise-wide information systems and data management strategies. Overseeing the digital transformation of healthcare services, the Senior Vice President, Chief Information Officer ensures that information architecture supports the delivery of vision, dental, and retirement planning solutions. This leadership role involves managing large-scale data initiatives to improve operational efficiency across North American locations. By implementing advanced analytics, Gary Anderson provides actionable insights that guide strategic decision-making. The Senior Vice President, Chief Information Officer collaborates with other C-suite leaders to integrate technology into every facet of the patient experience. Through the maintenance of high-performance computing environments, the Senior Vice President, Chief Information Officer supports the company's commitment to technological innovation. Ultimately, the Senior Vice President, Chief Information Officer safeguards the data assets of the organization, ensuring that information systems remain resilient and capable of meeting the complex demands of modern healthcare.

    Farley Kern - Chief Communications Officer

    Farley Kern, the Chief Communications Officer at GuideWell, directs the internal and external messaging strategies that define the company's market presence. Overseeing brand reputation and public relations, the Chief Communications Officer ensures that the value of integrated healthcare solutions reaches the target audience effectively. This leadership role involves crafting narratives that highlight the company's commitment to elderly care and specialized medical programs. By managing stakeholder engagement across North America, Farley Kern strengthens the connection between the organization and the communities served. The Chief Communications Officer collaborates with the executive team to ensure consistent communication of corporate values and strategic goals. Through the development of comprehensive communication plans, the Chief Communications Officer supports the growth of health insurance and retirement planning services. Ultimately, the Chief Communications Officer shapes the public perception of the company, ensuring that the mission of providing accessible, high-quality healthcare remains central to the brand identity.

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    Frequently Asked Questions Regarding GuideWell Top Executives and Leadership Team

    Who leads GuideWell?
    GuideWell is led by Brian Pieninck (President & Chief Executive Officer), along with executives such as Courtney Harris (Chief of Staff To the Office of the Chief Executive Officer) and David Petruzzellis (Chief Financial Officer, Government Business).
    Who is part of GuideWell’s executive team?
    The executive team of GuideWell includes leaders such as Brian Pieninck (President & Chief Executive Officer), Courtney Harris (Chief of Staff To the Office of the Chief Executive Officer), David Petruzzellis (Chief Financial Officer, Government Business) and other senior executives.
    How many executives does GuideWell have?
    GuideWell has 7 executives leading key business areas.
    What roles are included in GuideWell’s leadership team?
    The leadership team of GuideWell includes roles such as President & Chief Executive Officer, Chief of Staff To the Office of the Chief Executive Officer, Chief Financial Officer, Government Business, Senior VP, Health Care Services & President, Guidewell Health, Chief Technology Officer.