Full-Time

Senior Counsel

Product

Posted on 8/1/2026

Headway

Headway

1,001-5,000 employees

Connects patients with in-network therapists

Compensation Overview

$179.2k - $280k/yr

Remote in USA

Remote

Remote nationwide; candidates based in New York or San Francisco are preferred.

Category
Legal & Compliance (1)
Required Skills
Marketing

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Requirements
  • 5-7+ years of post-bar-admission legal experience with significant healthcare regulatory expertise, particularly in health technology and product counseling.
  • A deep understanding of multi-state healthcare regulations in evolving regulatory environments.
  • Experience serving as a trusted advisor to Engineering, Product, and/or Operations teams in a healthcare technology environment.
  • A proven ability to translate complex healthcare regulatory requirements into clear, actionable guidance for non-legal stakeholders.
  • A track record of balancing business risk appetite with business objectives in fast-paced organizations.
  • Strong communication skills and political savvy to navigate competing priorities and build effective partnerships.
  • A JD from an accredited law school and active bar membership in good standing, with the ability to register as New York in-house counsel required.
Responsibilities
  • Serve as an embedded regulatory thought partner to Engineering, Product, and partner Operations groups and pods, providing real-time guidance on the use of technology in healthcare delivery, artificial intelligence, and clinical modalities in health technology.
  • Translate complex artificial intelligence, data use, and healthcare laws and regulations, and related subregulatory guidance, into practical guidance and tools that Engineering, Product, and Operations teams can easily understand and implement, including the Telephone Consumer Protection Act, Children's Online Privacy Protection Act, CAN-SPAM, National Institute of Standards and Technology Artificial Intelligence Risk Management Framework and Generative Artificial Intelligence Profile, Food and Drug Administration Software as a Medical Device guidance, and Federal Trade Commission advertising, marketing, and health-claims guidance.
  • Anticipate regulatory challenges and proactively develop solutions that enable business objectives while mitigating risk.
  • Build strong relationships across teams to position guidance as a business enabler rather than an obstacle.

Headway builds a platform that makes mental healthcare easier to access and afford. For individuals, it helps users find therapists and psychiatrists who accept their insurance, letting them filter by preferences and compare thousands of providers so out-of-pocket costs are lower. For providers, it reduces administrative work related to insurance, enabling in-network care without the bureaucratic hassle. The product connects patients and providers through insurance-enabled matching and handles the related paperwork and billing so care can be more affordable and straightforward. Unlike networks that only list providers, Headway actively streamlines both sides of the process by coordinating with health plans and practices to maximize in-network care. The goal is to create a system where finding, paying for, and receiving therapy is simple, affordable, and accessible for more people.

Company Size

1,001-5,000

Company Stage

Late Stage VC

Total Funding

$327M

Headquarters

New York City, New York

Founded

2019

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Simplify Jobs

Simplify's Take

What believers are saying

  • Primary-care referrals can widen patient inflow quickly.
  • Near-immediate scheduling improves conversion in a waitlist-heavy market.
  • Insurance-backed access supports affordable, in-network therapy demand.

What critics are saying

  • Major payors can cut reimbursement and squeeze Headway margins.
  • Competitors like Alma and SonderMind can attract providers with better economics.
  • State licensing fragmentation can limit cross-state telehealth expansion.

What makes Headway unique

  • Insurance-first network with one-click booking and upfront copay transparency.
  • Provider software removes credentialing, claims, billing, and payment administration.
  • Nationwide network spans 50 states and major payors.

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Benefits

Equity Compensation

Medical, Dental, and Vision coverage

HSA / FSA

401K

Work-from-Home Stipend

Therapy Reimbursement

16-week parental leave for eligible employees

Carrot Fertility annual reimbursement and membership

13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st

Flexible Paid Time Off

Employee Assistance Program (EAP)

Training and professional development

Growth & Insights and Company News

Headcount

6 month growth

0%

1 year growth

0%

2 year growth

0%
Blue Cross and Blue Shield of New Mexico
May 13th, 2026
How behavioral health teams guide members to care.

How behavioral health teams guide members to care. May 13, 2026 Nearly a quarter of U.S. adults live with at least one mental health condition, and a growing number of people are seeking help. Yet even those with insurance can have trouble navigating care because they often aren't as familiar with their behavioral health benefits as they are with their medical benefits. Identifying in-network treatment and resources can be an overwhelming task, especially during a mental health dilemma. "They don't really know what their policies include," says behavioral health care coordinator Carmela Rupe. "I'm explaining the basics of insurance," she says, adding she often steers individual and family plan members toward in-network care and resources to help them find new providers and access covered in-person treatment centers to help control their conditions. Rupe is among teams of care coordinators at Blue Cross and Blue Shield of New Mexico providing behavioral health education, guidance and resources to help members find the care they need. Licensed in behavioral health care, they assist members seeking treatment for conditions, including anxiety, depression, substance misuse and autism, and avoid scammers targeting vulnerable people. "An insurance company is not necessarily viewed as the primary resource for behavioral health information," says Scott Bender, BCBSNM's executive director for behavioral health operations. "Many people will go to the internet to do a search or ask their friends and family for references. But that's a service we provide specifically in behavioral health." Although insured adults are more likely to receive mental health care than those without coverage, they still had difficulty accessing services, according to KFF. The health care policy nonprofit found nearly 45% of insured adults with mental health concerns could not get the mental health treatment they thought they needed. Depending on the plan, member resources include digital behavioral health tools and access to virtual and in-person providers. In 2025, BCBSNM launched a digital mental health hub available on the member account portal to improve resource access. More than 35,000 members have used the hub to find providers and educational tools. BCBSNM also has invested in Headway, a technology-enabled platform that connects and expands access for members to a diverse, national network of licensed therapists and psychiatrists. Care coordinators can offer guidance to appropriate levels of care, no matter whether members already have a diagnosis or are seeking treatment for the first time. They may also collaborate with other teams to coordinate medical care and medication compliance. "Seeking care can be very confusing," says Dr. Ella Williams, senior executive medical director for behavioral health. "There's just such a lack of knowledge about what's available to them. We want to increase people's awareness about the types of treatment and care that's covered." Rupe often reaches out to members to better coordinate their care if they've had at least two inpatient treatment admissions a year. She also ensures members receive their prescribed medications to maintain their physical and mental health. "We're real people who have been trained as masters-level individual clinicians," she says. "Our ethics as clinicians guide us. We want to help members get what they need." That expertise builds credibility with members, says Amy Wiley, a behavioral health case management coordinator. "Some members have never navigated the systems that are available to them," says Wiley, who's helped many members new to seeking behavioral health care. "They're overwhelmed because they don't know what they have." She always tries to provide members with educational information to help increase awareness, ease frustration and build trust. "We try to match members with the services they need," Wiley says. "We are really lucky in that we can spend more time with members to really dive in, ask questions and help take some of the legwork out of helping them find resources."

Blue Cross and Blue Shield of Illinois
May 12th, 2026
How behavioral health teams guide members to care.

How behavioral health teams guide members to care. May 12, 2026 Nearly a quarter of U.S. adults live with at least one mental health condition, and a growing number of people are seeking help. Yet even those with insurance can have trouble navigating care because they often aren't as familiar with their behavioral health benefits as they are with their medical benefits. Identifying in-network treatment and resources can be an overwhelming task, especially during a mental health dilemma. "They don't really know what their policies include," says behavioral health care coordinator Carmela Rupe. "I'm explaining the basics of insurance," she says, adding she often steers individual and family plan members toward in-network care and resources to help them find new providers and access covered in-person treatment centers to help control their conditions. Rupe is among teams of care coordinators at Blue Cross and Blue Shield of Illinois providing behavioral health education, guidance and resources to help members find the care they need. Licensed in behavioral health care, they assist members seeking treatment for conditions, including anxiety, depression, substance misuse and autism, and avoid scammers targeting vulnerable people. "An insurance company is not necessarily viewed as the primary resource for behavioral health information," says Scott Bender, executive director for behavioral health operations. "Many people will go to the internet to do a search or ask their friends and family for references. But that's a service we provide specifically in behavioral health." Although insured adults are more likely to receive mental health care than those without coverage, they still had difficulty accessing services, according to KFF. The health care policy nonprofit found nearly 45% of insured adults with mental health concerns could not get the mental health treatment they thought they needed. Depending on the plan, member resources include digital behavioral health tools and access to virtual and in-person providers. In 2025, BCBSIL launched a digital mental health hub available on the member account portal to improve resource access. More than 35,000 members have used the hub to find providers and educational tools. BCBSIL also has invested in Headway, a technology-enabled platform that connects and expands access for members to a diverse, national network of licensed therapists and psychiatrists. Care coordinators can offer guidance to appropriate levels of care, no matter whether members already have a diagnosis or are seeking treatment for the first time. They may also collaborate with other teams to coordinate medical care and medication compliance. "Seeking care can be very confusing," says Dr. Ella Williams, senior executive medical director for behavioral health. "There's just such a lack of knowledge about what's available to them. We want to increase people's awareness about the types of treatment and care that's covered." Rupe often reaches out to members to better coordinate their care if they've had at least two inpatient treatment admissions a year. She also ensures members receive their prescribed medications to maintain their physical and mental health. "We're real people who have been trained as masters-level individual clinicians," she says. "Our ethics as clinicians guide us. We want to help members get what they need." That expertise builds credibility with members, says Amy Wiley, a behavioral health case management coordinator. "Some members have never navigated the systems that are available to them," says Wiley, who's helped many members new to seeking behavioral health care. "They're overwhelmed because they don't know what they have." She always tries to provide members with educational information to help increase awareness, ease frustration and build trust. "We try to match members with the services they need," Wiley says. "We are really lucky in that we can spend more time with members to really dive in, ask questions and help take some of the legwork out of helping them find resources."

PR Newswire
Mar 31st, 2026
Headway Acquires Team Behind Tezi to Advance Human-Centered AI in Mental Health Care

/PRNewswire/ -- Headway, the company building a new mental healthcare system that everyone can access, today announced the acquisition of the team behind Tezi,...

GIANT Health
Sep 9th, 2025
Headway expands EHR with AI-assisted notes, embedded telehealth

Headway, a platform connecting patients with mental health providers covered by insurance, announced expanded EHR features for providers.

FxDailyInfo
May 25th, 2025
Headway Recognized as The Best Global Forex Broker 2025

May 25, 2025 - ForexDailyInfo.com, a leading authority in the forex industry, is proud to announce that Headway has been officially awarded the prestigious title of "The Best Global Forex Broker 2025".