Headway’s clinical leadership team, in partnership with our provider network
Our clinical leadership team is made up of practicing clinicians who relate to our provider network first-hand. These individuals are intimately familiar with both the clinical and administrative sides of running a practice, from accepting insurance, to managing clients and cases, and everything in between, making it possible to best advocate for our provider community.
In service of our mission to increase access to quality in-network mental health care, our clinical team helps to build systems and processes that empower clinicians and their practices while offering high-quality clinical guidance.
Simplify insurance and save time on your entire workflow — from compliance and billing to credentialing and admin.
Meet the team
Jeff Gould (he/him), M.D.
Sr. Medical Director, Head of Clinical
Dr. Jeff Gould is a board-certified adult and forensic psychiatrist. In his role as Medical Director at Headway, he works with the clinical team to ensure that the clinical care delivered at Headway is of the highest evidence-based standards. Prior to joining Headway, he managed clinical care and quality standards across hundreds of programs in a variety of settings including as Chief Physician of a large multi-state psychiatric hospital network and Department Chair at a Sutter hospital in the Bay Area. He also worked as the Behavioral Health Medical Director at Wheel and the Chief Medical Officer at Aware Healthcare. Dr. Gould is an Assistant Clinical Professor UCSF where he teaches and provides consultation to the courts on a wide variety of topics involving the interface between psychiatry and the law.
Practice specialties: Psychotic and mood disorders, psychopharmacology, civil and criminal litigation assessments
Practice status: Not currently accepting new patients
Nicole M. Benson (she/her), M.D., MBI
Medical Director
Dr. Nicole Benson is a child and adult psychiatrist, clinical informaticist, and mental health services researcher. As a Medical Director at Headway, she leverages her expertise in behavioral health and digital innovation to help transform mental health care delivery and expand access across the Headway network. Prior to Headway, she served as the Associate Chief Medical Information Officer at McLean Hospital and Medical Director for Digital Behavioral and Mental Health at Mass General Brigham where she led initiatives integrating cutting-edge technology into clinical practice to enhance patient care and streamline mental health services. She serves on the American Psychiatric Association Council for Quality Care and the American Academy of Child and Adolescent Psychiatry Mental Health IT committee. She maintains an appointment as an Assistant Professor at Harvard Medical School and continues to practice clinically.
Practice specialities: Treatment of children, adolescents, and adults; first episode psychosis; emergency psychiatry
Practice status: Not currently accepting new patients
Cary Crall (he/him), M.D.
Medical Director
Dr. Cary Crall is a board-certified adult psychiatrist. In his role as Medical Director at Headway, he works with the clinical team to ensure clinical care delivered through Headway is held to the highest evidence-based standard. In addition to his work at Headway, Dr. Crall is the Associate Medical Director at the Massachusetts General Hospital Department of Psychiatry. In addition, as faculty at Harvard Medical School, he enjoys mentoring and supervising trainees in specialty areas including management of OCD, minority stress, and Community Psychiatry. His research interests include psychosocial well-being of medically frail adolescents and the intersection of minority stress with emotional well-being and social functioning.
Practice specialties: Community psychiatry, transitional age youth and college mental health, telepsychiatry, psychopharm for OCD, integrated care models
Practice status: Currently maintains a waitlist and a reduced caseload
R. Andrew "Andy" Cruz (he/him), M.D.
Medical Director
Dr. Andy Cruz is a Harvard-trained adult psychiatrist and healthcare executive dedicated to expanding access to equitable behavioral healthcare. He previously served as Associate Medical Director for Massachusetts General Hospital's low-barrier substance use clinic, where he cultivated his passion for supporting individuals who use substances. Dr. Cruz is currently a Medical Director at Headway and Co-Founder & Chief Medical Officer at Guidelight Health. He is also a founding member of the Noble Forum and serves as an advisor for Steadfast Health. Committed to patient care, he continues to see patients in the Massachusetts General Hospital Emergency Department and the Bridge Clinic.
Practice specialties: Substance use, intermediate levels of care, emergency psychiatry
Practice status: Actively seeing patients in Massachusetts. Not currently accepting new patients.
Michael Heckendorn (he/him), LPC, NCC
Clinical Lead, Clinician Education
Michael is a Licensed Professional Counselor, Nationally Certified Counselor and active Headway provider. In his role as the Clinical Lead for Clinician Education, he develops educational frameworks and structures to assist clinicians throughout their journey with Headway. This includes onboarding new providers, offering continuous practice guidance, and delving into the realm of clinical best practices. As a therapist, Michael has worked in a variety of settings, including: private practice, k-12 schools, universities, and community mental health. Prior to joining Headway, he led clinical education at a teletherapy start-up focusing his efforts on best practices in remote clinical care.
Practice specialties: Adolescent and young adult mental health, anxiety, anger management, parenting adolescents, new paternal support, teletherapy
Practice status: Currently maintains a waitlist and a reduced caseload
Maddie Tong (she/her), LCSW
Senior Associate, Clinical Education
Maddie is a Licensed Clinical Social Worker whose practice draws from training in several modalities, including Cognitive Behavioral Therapy (CBT), Internal Family Systems Therapy (IFS), Psychodynamic Therapy, and Gottman Method Couples Therapy. Maddie has clinical training as an AASECT Certified Sex Therapist and operates from a trauma-informed lens. She has worked in both traditional settings, such as community mental health programs, as well as in the digital mental health tech space. Prior to joining Headway, Maddie was a Therapist and Clinical Content Manager at a digital start up, managing and creating clinical content in the form of courses, videos, webinars, and groups. While working at Headway, she maintains her private practice virtually. As a Senior Associate of Clinical Education at Headway, Maddie focuses her efforts on building out educational experiences to support Headway providers throughout their journey with Headway.
Practice specialities: Sex therapy, anxiety, codependency, trauma, relationship issues, life transitions
Practice status: Currently maintains a waitlist and reduced caseload
Ashlynn A. Johnson (she/her), MA
Senior Clinical Strategy Associate
Ashlynn is a clinical operations leader with a strong foundation in behavioral health, mental health, and health tech. As part of Headway’s Clinical Strategy team, she supports clinical leadership in driving strategic initiatives that enhance clinical programs, optimize operations, and streamline processes. Ashlynn provides project management and operational support across a range of initiatives, helping leaders execute cross-functional work and implement scalable, data-informed solutions that improve service delivery and team performance.
Prior to transitioning into health tech, Ashlynn worked extensively in behavioral crisis intervention and de-escalation across diverse care settings. She supported pediatric patients in long-term care at Children’s Specialized Hospital in New Jersey and later served on the psychiatric emergency and inpatient teams at NYC Health + Hospitals/Kings County, where she helped launch a first-of-its-kind inpatient program for adults with co-occurring intellectual disabilities and psychiatric conditions. She also worked at Children’s Healthcare of Atlanta providing behavioral support in emergency, ICU, and inpatient units.
Ashlynn holds a Master of Arts in Psychological Studies with a concentration in Behavior Analysis from Seton Hall University.
Growing your clientele can be a lot less complicated than you think. All you’ll need is a simple mindset shift and a couple basic strategies that help potential clients find and connect with you.
Navigating compliance can be time-consuming and stressful. We’re committed to changing that.
If the journey of one thousand miles begins with a single step, then the journey to starting or streamlining your insurance practice begins with a single call.
