Headway is building a new mental healthcare system that everyone can access. We make it easy for people to find quality in-network mental health care by removing historic barriers faced by mental health providers, payers, and patients. 

1 in 4 people in the US have a treatable mental health condition, but the vast majority do not get the care they need. The primary reason is cost: the majority of therapists do not accept insurance, meaning paying for therapy is prohibitively expensive for prospective patients. This is where we got our start – Headway has built the first software-enabled network of therapists who accept health insurance, making it easy for therapists to grow their practices, and possible for patients to find quality care they can afford. 

We launched in April of 2019 and are now powering 300,000+ appointments per month. To scale our vision, we’ve raised over $100 million in funding from a16z, Thrive, Accel, and Google Ventures.

Join us, and make an impact

We are looking for a top-notch problem-solver and communication whiz to guide our providers and patients through their experience on Headway.  

The CX Team’s mission is to deliver on the Headway promise to our providers, and in this role, you will ensure this mission through one-on-one interactions with our providers and patients. By working with our customers through email, live chat and phone you will guide them through any challenges, resolve their operational and technical issues, making Headway feel like magic. Guided by our principle of Handmade, Process-made, Product-made, you will consistently identify any trends and patterns in our providers' and patients' experience, and advocate for process and product changes to remove any friction and create a delightful Headway experience. 

Being results- and impact-driven, you thrive on helping providers/patients through any challenges they have on Headway. You enjoy delighting customers with every interaction, and solving any issues they have on Headway in a clear, friendly and effective way. Guided by our principle of making Headway feel like magic, you never miss a chance to elevate our customers' experience and work with your team to bring new and improved solutions to life. Being in healthcare tech, you thrive in a high-paced tech environment and have strong interest or prior experience in healthcare. 

You will: 

  • Deliver on the Headway promise. Driven by our mission and your love of problem-solving, you will effectively and empathetically help our providers and patients through any issues they encounter along their Headway user journey. 
  • Resolve inquiries for our Providers and Patients. Solve ~40 provider / patient inquiries via email, live chat and phone daily, Mon-Fri, consulting available resources and your team. 
  • Continuously learn and upskill. Being committed to ongoing growth and development, you will use available resources to continuously stay up-to-speed on Headway’s evolving product and service, and insurance practices. 
  • Advocate for our providers and patients: You will proactively surface frictions in customer experience, and propose process and product iterations, in the service of Headway’s mission 

You will love this job if...

  • Communication is your superpower. You have outstanding verbal and written communication skills; you’re succinct, clear, friendly, empathetic, and always solution-oriented.
  • You tackle challenging conversations head-on. You navigate sensitive and high-pressure client-facing situations and de-escalations with calm, poise and optimism. 
  • You have good judgment and discretion. You lead with integrity; you make thoughtful decisions with positive intent.  
  • You thrive with tactical goals. You’re competitive and seek to always meet and exceed targets while upholding the highest quality of your work.
  • You’re a passionate problem-solver. You enjoy a challenging scenario and you always seek to get to the root cause, and find elegant solutions for customers. 

Customer Experience Associates are expected to work occasional weekend shifts and may be scheduled to provide support during company holidays. Shifts are 9 hours with 1 hour for lunch and will be scheduled during the window of 8am - 9pm ET. Schedules may vary week to week. This position is not overtime exempt; those working over 40 hrs/ week will have the opportunity to earn 1.5x hourly compensation.

Candidates must have a quiet, private work space equipped with high-speed internet to fulfill shifts.

We believe a team's strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem - across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience.

Headway employees work remotely across the US, with the option to work from our NYC HQ. 

Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or to receive other benefits and privileges of employment, please contact talent@findheadway.com.

Apply for this Job

* Required
resume chosen  
(File types: pdf, doc, docx, txt, rtf)
cover_letter chosen  
(File types: pdf, doc, docx, txt, rtf)


Headway Custom Demographic Questions

We believe that to build the best startup team, we must build a diverse, equitable and inclusive team. We encourage people from all backgrounds to apply to all roles, and we proactively work to design hiring processes that mitigates bias. To help us track the parity in our candidate pipelines and efficacy of our recruiting efforts, please consider answering the following demographic questions. 

While completion of this survey is required, you will have the option to select “I don't wish to answer” for all questions. Your responses will be used (in aggregate only) to help us identify areas of improvement in our process.

Your responses will not be linked to your specific application and will not in any way be used in the hiring decision. 

I identify my gender as (Select one) *





I identify as transgender (Select one) *



I identify my sexual orientation as (Select one) *






I identify my ethnicity as *











Veteran status (Select one) *




Disability status (Select one) *