GuideWell Executive and Leadership Team

May, 2026

Leadership Overview

GuideWell has 7 executives leading key functions including strategy, technology, operations, finance, legal, and information systems.

Driven by a commitment to integrated health, GuideWell delivers comprehensive healthcare services, focusing on elderly care and leveraging digital platforms to provide a spectrum of medical and health solutions across North America.

Leadership Roles at GuideWell

  • President & Chief Executive Officer - Brian Pieninck
  • Senior Vice President, Chief of Staff, Office of the Chief Executive Officer - Lisa Lough
  • President & Chief Executive Officer, Florida Health Care Plans - Steven Blumberg
  • Chief Financial Officer, Government Business - David Petruzzellis
  • Chief Technology Officer - Robert Ruocco
  • Senior Vice President, Chief Information Officer - Gary Anderson
  • Executive Vice President & Chief Legal Officer, Corporate Affairs - Charles Joseph
  • Brian Pieninck - President & Chief Executive Officer

    Brian Pieninck, the President & Chief Executive Officer at GuideWell, directs the overarching strategy and operational execution for the healthcare services company. Pieninck guides the organization's focus on integrated health solutions, particularly emphasizing elderly care and the deployment of advanced digital platforms for service delivery. Overseeing the company's expansion across North America, Pieninck ensures the seamless integration of business-to-business and direct-to-consumer offerings, including health insurance plans, vision and dental coverage, and retirement planning. This leadership role involves aligning all departments with the company's mission to provide comprehensive medical and health services supported by robust technology infrastructure. Brian Pieninck's strategic vision drives GuideWell's market impact and commitment to innovation in healthcare delivery.
    Brian Pieninck

    Lisa Lough - Senior Vice President, Chief of Staff, Office of the Chief Executive Officer

    Lisa Lough, the Senior Vice President, Chief of Staff, Office of the Chief Executive Officer at GuideWell, provides strategic support and operational oversight directly to the CEO. Lough manages key initiatives and ensures alignment across various departments, facilitating the execution of GuideWell's integrated health solutions and elderly care focus. This role involves coordinating critical projects, optimizing internal processes, and enhancing communication channels to support the company's mission. Lisa Lough plays a pivotal part in translating the CEO's strategic directives into actionable plans, ensuring the efficient delivery of comprehensive medical and health services through digital platforms. The Chief of Staff's influence extends to driving operational excellence and supporting the company's growth across North America.

    Steven Blumberg - President & Chief Executive Officer, Florida Health Care Plans

    Steven Blumberg, the President & Chief Executive Officer, Florida Health Care Plans at GuideWell, leads the strategic direction and operational management of GuideWell's health insurance and medical services within Florida. Blumberg focuses on delivering integrated health solutions and specialized medical care programs tailored to the needs of the Florida market, with a particular emphasis on elderly care. This executive oversees the development and delivery of health insurance plans, vision and dental coverage, and retirement planning services, leveraging digital platforms for enhanced accessibility. Steven Blumberg's leadership ensures that Florida Health Care Plans effectively serves both business-to-business and direct-to-consumer segments, contributing significantly to GuideWell's overall mission and market presence in North America.

    David Petruzzellis - Chief Financial Officer, Government Business

    David Petruzzellis, the Chief Financial Officer, Government Business at GuideWell, manages the financial operations and strategic planning for the company's government-focused healthcare services. Petruzzellis oversees all fiscal aspects related to health insurance plans and medical programs serving government entities, ensuring financial health and compliance. This executive's role is critical in managing the financial intricacies of specialized medical care programs and retirement planning services, particularly those impacting elderly care populations. David Petruzzellis drives financial strategy to support the expansion of GuideWell's integrated health solutions and the effective deployment of its digital platforms within the government sector across North America. The Chief Financial Officer ensures robust financial stewardship for all government business initiatives.

    Robert Ruocco - Chief Technology Officer

    Robert Ruocco, the Chief Technology Officer at GuideWell, architects the company's technological vision and infrastructure to support integrated health solutions. Ruocco spearheads the development and implementation of digital platforms, including mobile applications, that are central to GuideWell's service delivery model, especially for elderly care. This executive ensures the advanced technology infrastructure underpins the company's comprehensive medical and health services, including health insurance, vision, and dental coverage. Overseeing all aspects of technology strategy, Robert Ruocco drives innovation to enhance both business-to-business and direct-to-consumer healthcare offerings across North America. The Chief Technology Officer's role is critical in maintaining GuideWell's competitive edge through cutting-edge technological advancements and operational efficiency.
    Robert Ruocco

    Gary Anderson - Senior Vice President, Chief Information Officer

    Gary Anderson, the Senior Vice President, Chief Information Officer at GuideWell, directs the company's information technology strategy and infrastructure to support its integrated health solutions. Anderson oversees the management of all IT systems, ensuring the reliability and security of the digital platforms, including mobile applications, that deliver GuideWell's comprehensive medical and health services. This leadership position is crucial for maintaining the advanced technology infrastructure that underpins health insurance plans, vision and dental coverage, and specialized elderly care programs. Gary Anderson's responsibilities include driving technological innovation to enhance operational efficiency and support the company's business-to-business and direct-to-consumer offerings across North America. The Chief Information Officer ensures IT capabilities align with GuideWell's strategic goals.
    Charles Joseph, the Executive Vice President & Chief Legal Officer, Corporate Affairs at GuideWell, provides comprehensive legal counsel and oversees corporate governance for the healthcare services company. Joseph directs all legal aspects related to GuideWell's integrated health solutions, including health insurance plans, vision and dental coverage, and specialized medical care programs. This executive ensures compliance with all regulatory requirements across North America, safeguarding the company's operations and strategic initiatives. Charles Joseph's responsibilities encompass managing corporate affairs, advising on legal risks associated with digital platforms and elderly care services, and supporting the company's mission through sound legal strategy. The Chief Legal Officer plays a vital role in maintaining GuideWell's integrity and facilitating its business objectives.

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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 Lisa Lough (Senior Vice President, Chief of Staff, Office of the Chief Executive Officer) and Steven Blumberg (President & Chief Executive Officer, Florida Health Care Plans).
    Who is part of GuideWell’s executive team?
    The executive team of GuideWell includes leaders such as Brian Pieninck (President & Chief Executive Officer), Lisa Lough (Senior Vice President, Chief of Staff, Office of the Chief Executive Officer), Steven Blumberg (President & Chief Executive Officer, Florida Health Care Plans) 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, Senior Vice President, Chief of Staff, Office of the Chief Executive Officer, President & Chief Executive Officer, Florida Health Care Plans, Chief Financial Officer, Government Business, Chief Technology Officer.