Headway Executive and Leadership Team

August, 2026

Leadership Overview

Headway has 9 executives leading key functions including strategy, revenue, technology, operations, staff management, human resources, product development, and medical oversight.

Focused on resolving the mental health affordability crisis, Headway builds a managed marketplace that simplifies benefit lookups, insurance claims, and claim status investigations to improve patient access.

Leadership Roles at Headway

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

    Breno Silv, the Chief Executive Officer at Headway, directs the overarching vision for the mental health marketplace. Silv architects the long-term strategy to bridge the gap between insurance providers and patients seeking affordable care. By aligning internal teams with the mission of simplifying benefit lookups and claims processing, the Chief Executive Officer ensures the platform remains the primary solution for mental health accessibility. Silv maintains constant communication with the Board to secure funding and support for rapid market expansion across the United States. Through rigorous oversight of the company's core business model, Breno Silv drives the organizational culture toward efficiency and patient-centric innovation. This leadership role involves navigating complex regulatory environments while scaling the marketplace to meet rising demand. Ultimately, Silv secures the financial and operational health of the enterprise, ensuring that the platform continues to solve the mental health affordability crisis through technological excellence.

    Rob Sadow - Chief Operating Officer

    Rob Sadow, the Chief Operating Officer at Headway, executes the daily operational strategy required to maintain a high-functioning mental health marketplace. Sadow architects the internal processes that govern claim status investigations and ancillary administrative actions, ensuring that the platform operates with maximum efficiency. The Chief Operating Officer drives the scaling of operational teams to support the company's expansion across diverse regional markets. By coordinating with the technology and product departments, Sadow ensures that operational workflows align with the software capabilities of the platform. Rob Sadow monitors the performance of the marketplace to identify bottlenecks in the claims process and implements solutions to improve provider satisfaction. This leadership role involves managing the logistical complexities of a managed marketplace to ensure consistent service delivery. Through meticulous oversight of operational metrics, Sadow secures the stability of the business, allowing the company to focus on its mission of making mental health care affordable and accessible.
    Rob Sadow

    Rutger Flohil - Chief Revenue Officer

    Rutger Flohil, the Chief Revenue Officer at Headway, manages the growth of the managed marketplace by optimizing insurance partnerships and provider acquisition. Flohil architects revenue streams by streamlining the integration of benefit lookups and claims status investigations into the provider workflow. The Chief Revenue Officer drives North American market penetration by demonstrating the value of the platform to large-scale healthcare networks. By coordinating with the sales and marketing departments, Flohil ensures that the value proposition of affordable mental health care reaches both clinicians and patients. Rutger Flohil monitors key performance indicators to adjust pricing models and partnership agreements, directly impacting the company's bottom line. This leadership role requires constant analysis of market trends to identify new opportunities for expansion. Through strategic planning and execution, Flohil secures sustainable revenue growth, allowing the company to scale operations while maintaining high standards of service for all marketplace participants.

    Andrew Ocheret - Chief Technology Officer

    Andrew Ocheret, the Chief Technology Officer at Headway, engineers the scalable software infrastructure that powers the mental health marketplace. Ocheret architects the technical framework for automated benefit lookups and real-time claims processing, ensuring seamless interactions between providers and insurance carriers. The Chief Technology Officer drives the development of secure, compliant systems that handle sensitive health data across the entire platform. By overseeing the engineering and data science teams, Ocheret ensures that the technology stack remains robust and capable of supporting rapid user growth. Andrew Ocheret collaborates with other C-suite leaders to translate business requirements into functional software features that solve the affordability crisis. This leadership role involves managing the technical roadmap to prioritize security, speed, and reliability. Through continuous innovation in software architecture, Ocheret maintains the competitive advantage of the platform, ensuring that clinicians and patients experience a frictionless digital environment for all mental health services.

    Tiffany Song - Chief of Staff

    Tiffany Song, the Chief of Staff at Headway, coordinates the strategic initiatives and executive communications that drive the company forward. Song architects the internal alignment between the leadership team and the broader organization, ensuring that the mission of solving the mental health affordability crisis remains the top priority. The Chief of Staff drives the execution of cross-functional projects, including the integration of new benefit lookup features and administrative improvements. By managing the executive office, Song facilitates decision-making processes and ensures that the leadership team remains focused on high-impact goals. Tiffany Song monitors the progress of key initiatives to ensure that the company meets its growth targets and operational milestones. This leadership role involves acting as a bridge between different departments to foster collaboration and transparency. Through effective project management and strategic support, Song secures the operational rhythm of the company, enabling the leadership team to execute the vision of a more accessible mental health system.

    Janice Warnke - Chief Human Resources Officer

    Janice Warnke, the Chief Human Resources Officer at Headway, directs the talent acquisition and organizational development strategies that support the company's mission. Warnke architects the culture and recruitment frameworks necessary to attract top-tier talent in the health-tech sector. The Chief Human Resources Officer drives the implementation of performance management systems that align individual contributions with the company's goal of solving the mental health affordability crisis. By overseeing employee engagement and professional development, Warnke ensures that the workforce remains motivated and capable of scaling the marketplace. Janice Warnke collaborates with the executive team to design compensation and benefits packages that reflect the company's commitment to health and wellness. This leadership role involves managing the human capital requirements of a rapidly growing startup to ensure organizational stability. Through strategic workforce planning, Warnke secures the talent necessary to innovate and maintain the platform's position as a leader in the mental health industry.

    Gabby Bonacci - Strategy & Operations Chief of Staff

    Gabby Bonacci, the Strategy & Operations Chief of Staff at Headway, directs the analytical frameworks that guide the company's operational expansion. Bonacci architects the strategic planning processes that allow the marketplace to scale efficiently while managing the complexities of insurance claims and benefit lookups. The Strategy & Operations Chief of Staff drives the evaluation of new market opportunities, ensuring that the company's resources are allocated to the most impactful areas. By analyzing operational data, Bonacci identifies trends that inform the long-term strategy for the platform. Gabby Bonacci collaborates with the operations and product teams to refine the user experience for both providers and patients. This leadership role involves translating high-level business goals into actionable operational plans that support the company's mission. Through rigorous strategic analysis and operational oversight, Bonacci secures the company's ability to navigate the competitive landscape and continue providing affordable mental health solutions to a growing user base.

    Emily Ryeom - Product Chief of Staff

    Emily Ryeom, the Product Chief of Staff at Headway, directs the product development lifecycle to ensure that the marketplace meets the needs of clinicians and patients. Ryeom architects the communication channels between the product team and other departments, ensuring that the development of new features for benefit lookups and claims processing remains aligned with the company's mission. The Product Chief of Staff drives the prioritization of the product roadmap, focusing on initiatives that directly reduce the mental health affordability crisis. By coordinating with the engineering and design teams, Ryeom ensures that the platform remains intuitive and efficient. Emily Ryeom monitors user feedback to identify areas for improvement and implements changes that enhance the overall value of the marketplace. This leadership role involves managing the product strategy to ensure that the company remains at the forefront of health-tech innovation. Through effective product management, Ryeom secures the platform's ability to deliver high-quality, accessible mental health services.

    Neha Chaudhary - Chief Medical Officer

    Neha Chaudhary, the Chief Medical Officer at Headway, directs the clinical standards and medical strategy that underpin the marketplace. Chaudhary architects the guidelines for provider quality and patient care, ensuring that the platform maintains high clinical integrity while simplifying the administrative burden of insurance claims. The Chief Medical Officer drives the integration of medical expertise into the product development process, ensuring that the software effectively supports the needs of mental health professionals. By collaborating with the operations and technology teams, Chaudhary ensures that the platform's features for benefit lookups and claim status investigations are clinically relevant and accurate. Neha Chaudhary represents the company in discussions with healthcare networks to advocate for better access to mental health services. This leadership role involves overseeing the clinical quality of the marketplace to ensure that patients receive the best possible care. Through medical leadership, Chaudhary secures the trust of both providers and patients, reinforcing the company's mission.
    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 Rob Sadow (Chief Operating Officer) and Rutger Flohil (Chief Revenue Officer).
    Who is part of Headway’s executive team?
    The executive team of Headway includes leaders such as Breno Silv (Chief Executive Officer), Rob Sadow (Chief Operating Officer), Rutger Flohil (Chief Revenue Officer) and other senior executives.
    How many executives does Headway have?
    Headway has 9 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, Chief Operating Officer, Chief Revenue Officer, Chief Technology Officer, Chief of Staff.