MedicareInsurance.Com Executive and Leadership Team

November, 2026

Leadership Overview

MedicareInsurance.Com has 4 executives leading key functions including strategic operations, financial oversight, and technology infrastructure.

Committed to simplifying complex healthcare decisions, MedicareInsurance.Com empowers individuals to navigate Medicare Advantage options through transparent comparison tools and expert guidance from licensed insurance professionals.

Leadership Roles at MedicareInsurance.Com

  • Chief Financial Officer - Chandra Clines
  • Chief Technology Officer - Brent LeBlanc
  • Managing Director - Benjamin Tewes
  • Managing Director - Mark MacFawn
  • Chandra Clines - Chief Financial Officer

    Chandra Clines, the Chief Financial Officer at MedicareInsurance.Com, manages the fiscal health and long-term financial planning of the agency. Overseeing capital allocation and revenue growth strategies, Clines ensures that the organization maintains the necessary resources to support its digital comparison tools and agent services. This leadership role involves rigorous financial modeling to assess the impact of various Medicare Advantage market shifts on the company's bottom line. Chandra Clines coordinates with other executive leaders to align budgetary priorities with the strategic goals of Health Insurance Associates, LLC. By implementing robust financial controls and reporting mechanisms, Clines secures the stability required for continued innovation in the insurance sector. The Chief Financial Officer monitors industry-wide economic trends to mitigate risks, ultimately supporting the agency's ability to provide consistent, high-quality service to clients across the country while maintaining a strong competitive position.
    Chandra Clines

    Brent LeBlanc - Chief Technology Officer

    Brent LeBlanc, the Chief Technology Officer at MedicareInsurance.Com, architects the digital infrastructure that powers the company's Medicare comparison and enrollment platform. Directing the development of user-friendly interfaces, LeBlanc ensures that the technology stack remains secure, scalable, and capable of handling complex data from major insurance carriers. This leadership role involves overseeing the integration of advanced analytics to improve the accuracy of plan recommendations for users. Brent LeBlanc manages the engineering teams responsible for maintaining the reliability of the online shopping experience, ensuring that the platform functions optimally for individuals seeking coverage. By prioritizing cybersecurity and data integrity, LeBlanc protects sensitive client information while driving technological advancements that simplify the Medicare process. The Chief Technology Officer continuously evaluates emerging digital tools to enhance the agency's market reach and operational efficiency, ensuring that the technology remains a core competitive advantage.

    Benjamin Tewes - Managing Director

    Benjamin Tewes, the Managing Director at MedicareInsurance.Com, directs the overarching strategic vision for the agency. Focusing on the expansion of Medicare Advantage plan accessibility, Tewes architects high-level partnerships with major carriers such as Humana and Aetna. This leadership role involves refining the consumer experience to ensure seamless enrollment processes across the United States. By analyzing market trends in the health insurance sector, Benjamin Tewes identifies growth opportunities that align with the mission of simplifying coverage choices for seniors. The Managing Director maintains rigorous standards for compliance and service quality, ensuring that the agency remains a trusted resource for beneficiaries. Through constant evaluation of operational performance, Tewes drives the organization toward sustainable market leadership while maintaining a focus on client-centric insurance solutions that address diverse healthcare needs in a competitive landscape.

    Mark MacFawn - Managing Director

    Mark MacFawn, the Managing Director at MedicareInsurance.Com, oversees the internal scaling and operational efficiency of the agency. Concentrating on the optimization of licensed insurance agent workflows, MacFawn implements training programs that enhance the quality of guidance provided to clients navigating Medicare options. This leadership role involves managing the day-to-day execution of service delivery to ensure that every user receives accurate information regarding UnitedHealthcare and other major carrier plans. Mark MacFawn monitors regional performance metrics to identify areas for process improvement, thereby increasing the effectiveness of the agency's support infrastructure. By fostering a culture of operational excellence, MacFawn ensures that the organization meets the evolving demands of the insurance market. The Managing Director consistently aligns internal resources with the broader goal of providing accessible, reliable, and transparent health insurance information to individuals nationwide.

    Frequently Asked Questions Regarding MedicareInsurance.Com Top Executives and Leadership Team

    Who leads MedicareInsurance.Com?
    MedicareInsurance.Com is led by Chandra Clines (Chief Financial Officer), along with executives such as Brent LeBlanc (Chief Technology Officer) and Benjamin Tewes (Managing Director).
    Who is part of MedicareInsurance.Com’s executive team?
    The executive team of MedicareInsurance.Com includes leaders such as Chandra Clines (Chief Financial Officer), Brent LeBlanc (Chief Technology Officer), Benjamin Tewes (Managing Director) and other senior executives.
    How many executives does MedicareInsurance.Com have?
    MedicareInsurance.Com has 4 executives leading key business areas.
    What roles are included in MedicareInsurance.Com’s leadership team?
    The leadership team of MedicareInsurance.Com includes roles such as Chief Financial Officer, Chief Technology Officer, Managing Director, Managing Director.