Headway Executive and Leadership Team

July, 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 solve mental healths affordability crisis, Headway focuses on executing benefit lookups, claims, and claim status investigations to ensure accessible care.

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 Revenue Officer - Rutger Flohil
  • Chief of Staff - Tiffany Song
  • Product Chief of Staff - Emily Ryeom
  • Chief Human Resources Officer - Janice Warnke
  • Strategy & Operations Chief of Staff - Gabrielle Anselmi
  • 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 mission to address mental health affordability by optimizing managed marketplace functions. This leadership involves aligning departmental objectives with the core business model of simplifying benefit lookups and claims processing. Silv ensures the company's strategic direction supports market expansion and innovation within the health tech sector. The Chief Executive Officer's role is pivotal in fostering a culture of efficiency and impact, driving Headway's commitment to accessible mental healthcare solutions. Silv's oversight extends to key performance indicators that measure success in claim status investigation and ancillary service delivery, solidifying Headway's position in the New York City market and beyond.

    Andrew Adams - Founder & Chief Executive Officer

    Andrew Adams, the Founder & Chief Executive Officer at Headway, establishes the foundational vision and strategic imperatives for the organization. Adams drives the company's core mission to dismantle the mental health affordability crisis through innovative solutions. This leadership role encompasses guiding the development and execution of Headway's managed marketplace, focusing on critical functions like benefit lookups and claims management. Adams ensures that operational strategies directly support the company's objective of making mental healthcare more accessible. The Founder & Chief Executive Officer's influence is critical in shaping the company culture and directing long-term growth initiatives. Adams's commitment to resolving complex claims and investigating claim statuses reinforces Headway's dedication to service excellence and market impact.

    Robert Sadow - Chief Operating Officer

    Robert Sadow, the Chief Operating Officer at Headway, executes the operational strategies that enable the company's mission to solve mental health affordability. Sadow oversees the day-to-day functions critical to the managed marketplace, including the precise execution of benefit lookups and claims management. This role is central to ensuring operational efficiency and service quality across all departments. Sadow's leadership focuses on optimizing processes for claim status investigation and other related ancillary actions, directly impacting user experience and provider satisfaction. The Chief Operating Officer ensures that Headway's operational framework supports rapid scaling and sustained growth, particularly within the New York City market. Robert Sadow's commitment to operational excellence is fundamental to Headway's ability to deliver accessible mental healthcare solutions.
    Robert Sadow

    Andrew Ocheret - Chief Technology Officer

    Andrew Ocheret, the Chief Technology Officer at Headway, architects the technological infrastructure that powers the company's mission. Ocheret directs the development and implementation of scalable software solutions designed to streamline mental health benefit lookups and claims processing. This leadership position involves overseeing all aspects of technology strategy, ensuring robust data security and system reliability for sensitive health information. Ocheret's focus is on leveraging cutting-edge technology to enhance the efficiency of claim status investigations and related ancillary actions. The Chief Technology Officer ensures that Headway's platform effectively addresses the complexities of the healthcare system, making mental health services more affordable and accessible. Ocheret's technical vision is crucial for maintaining a competitive edge and driving innovation in the health tech landscape.

    Rutger Flohil - Chief Revenue Officer

    Rutger Flohil, the Chief Revenue Officer at Headway, drives the commercial strategy and revenue generation initiatives. Flohil leads efforts to expand Headway's market reach and secure partnerships that advance the company's mission of making mental healthcare affordable. This executive role involves developing and implementing sales strategies that align with the core business objectives of simplifying benefit lookups and claims processing. Flohil's focus is on building sustainable revenue streams by demonstrating the value of Headway's solutions to employers and health plans. The Chief Revenue Officer plays a key part in translating the company's technological capabilities into tangible financial growth. Rutger Flohil's leadership ensures that Headway's commercial success directly contributes to its impact on mental health accessibility.

    Tiffany Song - Chief of Staff

    Tiffany Song, the Chief of Staff at Headway, provides strategic support and operational coordination across executive functions. Song facilitates the execution of key initiatives that advance Headway's mission to address mental health affordability. This role involves managing cross-functional projects, optimizing internal communication, and ensuring alignment with the company's strategic goals. Song's responsibilities include streamlining processes related to benefit lookups and claims management, enhancing overall operational effectiveness. The Chief of Staff acts as a critical liaison, connecting different departments to drive progress on complex operational challenges. Tiffany Song's contributions are vital in ensuring that Headway operates with maximum efficiency and impact in its pursuit of accessible mental healthcare.

    Emily Ryeom - Product Chief of Staff

    Emily Ryeom, the Product Chief of Staff at Headway, enhances the strategic direction and execution of product development initiatives. Ryeom collaborates closely with product teams to ensure that Headway's offerings effectively address the mental health affordability crisis. This position involves translating market needs and company objectives into actionable product roadmaps, focusing on features that simplify benefit lookups and claims processing. Ryeom's role is crucial in optimizing the product lifecycle, from ideation through to launch and iteration. The Product Chief of Staff ensures that product strategies align with the overall business mission and contribute to improved claim status investigation capabilities. Emily Ryeom's focus on product excellence drives Headway's innovation in delivering accessible mental healthcare solutions.

    Janice Warnke - Chief Human Resources Officer

    Janice Warnke, the Chief Human Resources Officer at Headway, directs the human capital strategy to support the company's growth and mission. Warnke oversees all aspects of talent management, employee engagement, and organizational development, ensuring Headway attracts and retains top talent. This leadership role is critical in fostering a company culture that aligns with Headway's commitment to solving mental health affordability. Warnke's focus includes developing programs that support employee well-being and professional growth, essential for a team dedicated to complex tasks like benefit lookups and claims investigation. The Chief Human Resources Officer ensures that the workforce is equipped and motivated to drive Headway's success in making mental healthcare accessible. Janice Warnke's strategic HR leadership is fundamental to building a high-performing organization.

    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 Headway's managed marketplace, particularly in executing benefit lookups and managing claims. This role involves analyzing operational data to identify areas for optimization and implementing solutions that support the company's mission to resolve mental health affordability issues. Anselmi works to ensure seamless integration between strategic objectives and day-to-day operations, facilitating effective claim status investigation. The Strategy & Operations Chief of Staff plays a key part in translating high-level strategy into executable operational plans. Gabrielle Anselmi's contributions are vital for maintaining Headway's agility and effectiveness in delivering accessible mental healthcare.

    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 services. Chaudhary guides Headway's approach to mental healthcare, ensuring that operational processes like benefit lookups and claims management align with best clinical practices. This role is essential for maintaining the integrity and effectiveness of the services offered, directly supporting the mission to make mental health affordable. Chaudhary's oversight ensures that the company's technology and operations support patient needs and clinical quality. The Chief Medical Officer plays a critical part in shaping Headway's strategy for delivering accessible and high-quality mental healthcare solutions. Neha Chaudhary's medical insights are fundamental to Headway's impact in the health tech sector.
    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 Revenue Officer.