Headway Executive and Leadership Team

June, 2026

Leadership Overview

Headway has 10 executives leading key functions including strategy, technology, operations, revenue, human resources, and medical affairs.

Driven by a mission to democratize mental healthcare access, Headway operates as a managed marketplace, directly addressing the affordability crisis through innovative solutions and comprehensive benefit management.

Leadership Roles at Headway

  • Chief Executive Officer - Breno Silv
  • Founder & Chief Executive Officer - Andrew Adams
  • Chief Operating Officer - Robert Sadow
  • Chief Technology Officer - Andrew Ocheret
  • Chief of Staff - Tiffany Song
  • Chief Revenue Officer - Rutger Flohil
  • Product Chief of Staff - Emily Ryeom
  • Strategy & Operations Chief of Staff - Gabrielle Anselmi
  • Chief Human Resources Officer - Janice Warnke
  • Chief Medical Officer - Neha Chaudhary
  • Breno Silv - Chief Executive Officer

    Breno Silv, the Chief Executive Officer at Headway, directs the overarching corporate strategy and operational execution. Silv guides the company's expansion efforts, focusing on scaling the managed marketplace to meet the growing demand for affordable mental health services. This leadership role involves fostering strategic partnerships and ensuring the company's financial health and long-term viability. By championing innovation, Breno Silv drives the development of new service offerings that enhance the user experience and broaden access to care. The Chief Executive Officer's vision shapes Headway's market position and its commitment to solving the mental health affordability crisis.

    Andrew Adams - Founder & Chief Executive Officer

    Andrew Adams, the Founder & Chief Executive Officer at Headway, establishes the foundational vision and strategic direction for the organization. Adams spearheads initiatives aimed at disrupting the mental health landscape by tackling affordability barriers. This executive guides the company's growth trajectory, ensuring alignment with its core mission of making mental healthcare accessible. The Founder & Chief Executive Officer's leadership cultivates a culture of innovation and impact, driving the development of solutions that address critical market needs. Andrew Adams's strategic oversight is pivotal in navigating the complexities of the healthcare industry and solidifying Headway's position as a leader in the managed marketplace.

    Robert Sadow - Chief Operating Officer

    Robert Sadow, the Chief Operating Officer at Headway, directs the day-to-day operational functions and ensures the seamless execution of the company's service delivery model. Sadow oversees the critical processes of benefit lookups, claims management, and claim status investigations, optimizing workflows for maximum efficiency and accuracy. This leadership position is vital in maintaining the integrity and effectiveness of the managed marketplace, directly supporting Headway's commitment to affordability. The Chief Operating Officer's focus on operational excellence ensures that the company can scale its services effectively across its user base. Robert Sadow's strategic management of operations is key to Headway's ability to navigate the complexities of the healthcare system and deliver on its promise.
    Robert Sadow

    Andrew Ocheret - Chief Technology Officer

    Andrew Ocheret, the Chief Technology Officer at Headway, architects and oversees the company's entire technology infrastructure and development roadmap. Ocheret drives the innovation of the managed marketplace platform, ensuring its scalability, security, and efficiency in handling complex benefit lookups and claims processing. This role is critical in translating business objectives into robust technological solutions that directly support Headway's mission to solve mental health affordability. The Chief Technology Officer's expertise ensures the platform effectively manages claims, claim status investigations, and other ancillary actions. Andrew Ocheret's leadership in technology development is fundamental to Headway's operational success and its ability to deliver seamless services to users.

    Tiffany Song - Chief of Staff

    Tiffany Song, the Chief of Staff at Headway, provides strategic support and operational coordination across various departments, ensuring alignment with the company's overarching goals. Song facilitates critical cross-functional initiatives, enhancing communication and driving project execution within the managed marketplace. This role is instrumental in streamlining operations related to benefit lookups and claims processing, ensuring that Headway effectively addresses mental health affordability. The Chief of Staff's responsibilities include managing key strategic projects and supporting executive leadership in decision-making processes. Tiffany Song's contributions are vital to maintaining operational momentum and advancing Headway's mission to democratize mental healthcare access.

    Rutger Flohil - Chief Revenue Officer

    Rutger Flohil, the Chief Revenue Officer at Headway, spearheads all revenue-generating activities and drives the company's commercial strategy. Flohil focuses on expanding market penetration and developing strategic partnerships that enhance Headway's ability to provide affordable mental health solutions. This executive leads the sales and business development teams, ensuring they effectively communicate the value proposition of the managed marketplace. The Chief Revenue Officer's efforts are critical in scaling the business and achieving financial objectives while upholding the mission to solve mental health affordability. Rutger Flohil's leadership in revenue generation is essential for Headway's sustainable growth and its impact on the healthcare sector.

    Emily Ryeom - Product Chief of Staff

    Emily Ryeom, the Product Chief of Staff at Headway, enhances the product development lifecycle and ensures strategic alignment across product teams. Ryeom collaborates closely with product leadership to refine the managed marketplace features, focusing on improving benefit lookup accuracy and claims management efficiency. This role is crucial in translating market needs into actionable product strategies that directly address mental health affordability. The Product Chief of Staff's contributions are vital for optimizing the user experience and ensuring the platform effectively supports ancillary actions. Emily Ryeom's strategic input drives product innovation, reinforcing Headway's commitment to accessible mental healthcare solutions.

    Gabrielle Anselmi - Strategy & Operations Chief of Staff

    Gabrielle Anselmi, the Strategy & Operations Chief of Staff at Headway, drives strategic planning and operational improvements across the organization. Anselmi focuses on enhancing the efficiency of core processes, including benefit lookups and claims investigation, to better serve Headway's mission of affordable mental healthcare. This executive plays a key part in optimizing operational workflows and ensuring strategic initiatives are executed effectively. The Strategy & Operations Chief of Staff's role is critical in aligning departmental efforts with the company's broader objectives. Gabrielle Anselmi's strategic insights and operational focus are essential for Headway's continued growth and its impact on the mental health sector.

    Janice Warnke - Chief Human Resources Officer

    Janice Warnke, the Chief Human Resources Officer at Headway, leads all human capital strategies and fosters a robust organizational culture. Warnke focuses on attracting, developing, and retaining top talent essential for driving Headway's mission to solve mental health affordability. This executive oversees employee engagement, talent management, and the development of HR policies that support the company's growth and operational needs. The Chief Human Resources Officer's leadership ensures that Headway has the skilled workforce necessary to manage complex benefit lookups and claims processes effectively. Janice Warnke's commitment to people operations is fundamental to Headway's success and its ability to deliver on its promise of accessible care.

    Neha Chaudhary - Chief Medical Officer

    Neha Chaudhary, the Chief Medical Officer at Headway, provides clinical leadership and ensures the integration of medical expertise into the company's service offerings. Chaudhary guides the strategic direction for clinical operations, focusing on enhancing the quality and accessibility of mental healthcare services provided through the managed marketplace. This role is critical in ensuring that Headway's solutions effectively address patient needs and align with best medical practices. The Chief Medical Officer's oversight is vital for navigating the healthcare landscape and upholding the company's commitment to affordability. Neha Chaudhary's clinical acumen is essential for Headway's mission to democratize mental health access.
    Neha Chaudhary

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    Frequently Asked Questions Regarding Headway Top Executives and Leadership Team

    Who leads Headway?
    Headway is led by Breno Silv (Chief Executive Officer), along with executives such as Andrew Adams (Founder & Chief Executive Officer) and Robert Sadow (Chief Operating Officer).
    Who is part of Headway’s executive team?
    The executive team of Headway includes leaders such as Breno Silv (Chief Executive Officer), Andrew Adams (Founder & Chief Executive Officer), Robert Sadow (Chief Operating Officer) and other senior executives.
    How many executives does Headway have?
    Headway has 10 executives leading key business areas.
    What roles are included in Headway’s leadership team?
    The leadership team of Headway includes roles such as Chief Executive Officer, Founder & Chief Executive Officer, Chief Operating Officer, Chief Technology Officer, Chief of Staff.