[All remote jobs](https://jobicy.com/jobs.md)[![Headway.co logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2021/12/068391a61855fb604bca051cafe3c510.jpeg)](https://jobicy.com/company/headway.md)[Headway.co](https://jobicy.com/company/headway.md) # Senior Counsel, Product Review the role, location requirements, compensation details, and application process before deciding whether this opportunity fits your next career move. [Apply for this job](#job-application)[View company](https://jobicy.com/company/headway.md)ShareRemote from[USA](https://jobicy.com/job-region/usa.md)SalaryUSD 224k–280k / yrDepartment[Legal & Compliance](https://jobicy.com/categories/legal.md)EmploymentFull TimeExperienceSeniorPublished1 Nov 2026Apply before1 Dec 2026Listing views66Application actions3Application toolkit ## Make your next move. Prepare your resume, explore your fit, and draft a cover letter for this opportunity. AI Summary ## The role, at a glance. Headway is seeking a Senior Counsel, Product to advise product, engineering, and operations teams at a rapidly growing healthcare technology company. The role focuses on translating healthcare, AI, privacy, data-use, and consumer-protection requirements into practical guidance for technology products. The attorney will act as an embedded strategic partner, anticipate regulatory risks, and help teams pursue innovation while managing legal exposure. Candidates need 5–7+ years of post-bar legal experience, substantial health-tech regulatory knowledge, and an active bar membership. This is a remote-first, full-time role open to candidates nationwide in the United States. ## Role DNA A quick view of the complexity, pace, ownership and collaboration implied by the job description. ### Job Complexity 5/5EasyHard ### Pace & Pressure 5/5RelaxedFast-paced ### Autonomy Level 5/5GuidedFull ownership ### Communication Load 5/5IndependentCollaborative AI insightThis is a senior, high-autonomy legal role involving complex and evolving intersections of healthcare regulation, AI, data use, and software products. Success requires independently balancing regulatory risk with fast-moving product priorities and influencing diverse non-legal stakeholders. ## Salary analysis Estimated compensation compared with the broader US market for similar roles. Estimated job median (per year)Market rate$252,000US market range (per year)$220k–$300k0$330k AI insightThe employer discloses an annual base compensation range of $224,000–$280,000 USD, with a midpoint of $252,000. This is a credible range for a senior product counsel specializing in healthcare technology, AI, and regulatory matters in the US market. Estimated market compensation is $220,000–$300,000 USD annually, varying by legal depth, health-tech expertise, location, and scope of product responsibility. ## Core skills Skills and capabilities most closely associated with this opportunity. [Healthcare regulatory compliance](https://jobicy.com/jobs?search_keywords=Healthcare%20regulatory%20compliance.md)[Product counseling](https://jobicy.com/jobs?search_keywords=Product%20counseling.md)[Health technology law](https://jobicy.com/jobs?search_keywords=Health%20technology%20law.md)[Artificial intelligence governance](https://jobicy.com/jobs?search_keywords=Artificial%20intelligence%20governance.md)[Data privacy](https://jobicy.com/jobs?search_keywords=Data%20privacy.md)[Healthcare data use](https://jobicy.com/jobs?search_keywords=Healthcare%20data%20use.md)[FDA Software as a Medical Device](https://jobicy.com/jobs?search_keywords=FDA%20Software%20as%20a%20Medical%20Device.md)[TCPA compliance](https://jobicy.com/jobs?search_keywords=TCPA%20compliance.md)[COPPA compliance](https://jobicy.com/jobs?search_keywords=COPPA%20compliance.md)[CAN-SPAM compliance](https://jobicy.com/jobs?search_keywords=CAN-SPAM%20compliance.md)[FTC advertising compliance](https://jobicy.com/jobs?search_keywords=FTC%20advertising%20compliance.md)[NIST AI Risk Management Framework](https://jobicy.com/jobs?search_keywords=NIST%20AI%20Risk%20Management%20Framework.md)[Legal risk assessment](https://jobicy.com/jobs?search_keywords=Legal%20risk%20assessment.md)[Cross-functional collaboration](https://jobicy.com/jobs?search_keywords=Cross-functional%20collaboration.md)[Legal communication](https://jobicy.com/jobs?search_keywords=Legal%20communication.md) Sample interview questionsHow would you advise a product team that wants to launch an AI-enabled feature using sensitive healthcare information?I would first map the data flows, intended use, user populations, model inputs and outputs, and decision-making impact. I would assess applicable healthcare privacy, consumer-protection, AI governance, and clinical regulations, then translate findings into concrete product requirements such as consent, data minimization, validation, disclosures, human oversight, and monitoring controls. Describe how you translate complex healthcare regulations for engineers and product managers. I begin with the business objective and identify the legal requirements that materially affect the proposed workflow. I provide concise, actionable guidance through decision trees, product requirements, launch checklists, and examples rather than relying solely on legal analysis. I also explain the risk level and viable options so teams can make informed decisions efficiently. How would you evaluate whether a digital health feature could be regulated as Software as a Medical Device? I would examine the feature's intended use, claims, target users, inputs, outputs, and whether it informs or drives clinical decisions. I would assess FDA guidance and applicable enforcement posture, distinguish administrative or wellness functionality from clinical functionality, and recommend product, documentation, validation, and marketing guardrails appropriate to the risk. How do you balance a company's risk appetite with urgent product-launch timelines? I prioritize risks by likelihood, severity, regulatory exposure, and reversibility. Rather than simply blocking a launch, I work with stakeholders to identify mitigations, phased releases, scope limitations, disclosures, and monitoring that allow progress while addressing material concerns. I document decisions and escalate only when residual risk exceeds agreed business tolerance. What would you do if engineering and marketing disagreed about claims for an AI-powered healthcare product? I would align both groups around the evidence supporting the claim, the product's actual capabilities, and the relevant FTC, FDA, and healthcare standards. I would propose substantiated, consumer-clear language that accurately describes the feature and avoids implying unsupported clinical outcomes. If needed, I would establish a repeatable claims-review process for future launches. Opportunity details ## About this role. 1 in 4 people in the US have a treatable mental health condition, but most providers don’t accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work – credentialing, claims, payment reconciliation – is a nightmare. We’ve automated that. But we’re going further. Over 90,000 providers across all 50 states run their practice on our software, serving over 2.6 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale, and building much of it with AI. We aren’t just a billing layer; we are becoming the platform where care actually happens. We’re a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.), looking for exceptional people to help us achieve this mission. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better. As Senior Counsel, Product, you will be a key strategic partner responsible for partnering with our R&D (product and engineering) teams to support innovation during a pivotal growth phase. This is a unique opportunity to join a mission-driven healthcare technology company where legal is viewed as a strategic partner rather than a roadblock. You will serve as the primary product attorney and thought partner for specific Headway’s Product and Engineering team groups and pods, with particular focus on AI, data usage, and health laws and regulations that impact the build of innovative technology products. This is a remote first role so we will consider candidates nationwide. In this role, you will: * Serve as embedded regulatory thought partner to Engineering, Product and partner Operations groups and pods, providing real-time guidance on use of technology in healthcare delivery, AI, and clinical modalities in health technology. * Translate complex AI, 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. These include but are not limited to: TCPA, COPPA, CAN-SPAM, NIST AI RMF and the Generative AI Profile, FDA Software as a Medical Device, FTC Advertising and Marketing and Health Claims marketing 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 You would be a great fit if you have: * 5-7+ years of post bar admittance legal experience with significant healthcare regulatory expertise, particularly in health technology and product counseling * 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 * Proven ability to translate complex healthcare regulatory requirements into clear, actionable guidance for non-legal stakeholders * 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 * JD from accredited law school and active bar membership in good standing (ability to register as NY in-house counsel) ### Comprehensive benefits: Medical, dental, vision, HSA/FSA, 401(k) including match for 2027!, Carrot Fertility reimbursement, and paid parental, medical and caregiver leave. 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 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 receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview. Headway participates in E-Verify. To learn more, click [here.](https://www.e-verify.gov/sites/default/files/everify/posters/EVerifyParticipationPoster.pdf) A notice to Headway applicants: To protect yourself against phishing and recruitment fraud, please note that Headway only accepts applications through our official careers page at [https://headway.co/careers](https://headway.co/careers). Headway will never refer you to external websites, ask for payment or personal information, or conduct interviews via messaging apps. All official communication will come from a @[findheadway.com](http://findheadway.com) email address. If you are contacted by someone claiming to be from Headway via an unofficial channel, please do not share any information and report it as spam. 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