Staff Product Manager

Hard Problems; United States; Remote; USD 212,000 - 265,000; Full time

Benefits offered by this job

Equity compensation

Medical

Dental

Vision coverage

HSA and FSA options

401K plan

Work-from-home stipend

therapy reimbursement

16 weeks of parental leave

Carrot Fertility annual reimbursement

13 paid holidays per year plus a break

Flexible paid time off

Employee Assistance Program

Training and professional development

Job summary

Headway is seeking Senior, Staff, and Principal Product Managers to own end-to-end product areas across Patient, Provider, Payer, and Platform domains. You will shape strategy, drive AI-enabled outcomes, and partner with engineering, data science, design, clinical, and operations teams to move the business forward.

You will lead AI initiatives, define success metrics, and advocate for customer-centered decisions grounded in data and research.

Qualifications

• Eight+ years of product management experience with a track record of owning complex, high-impact product areas.
• Experience with LLM systems, including prompting, retrieval, evaluation, and fine-tuning, and shipping AI-powered products at scale.
• Experience building at scale in a marketplace, platform, or data-intensive environment with measurable outcomes.
• Comfort working in regulated, complex industries and influencing across engineering, clinical, legal, finance, and operations.

Responsibilities

• Define and own the product strategy for your area in partnership with engineering, design, data, clinical, and operations teams.
• Identify where AI delivers step-change improvements and drive bets from insight to production.
• Set and own clear success metrics, report results to stakeholders, and adjust course with urgency.
• Represent the voice of customers (patients, providers, or health plans) grounded in data and research.

Skills

8+ years PM experience

LLM systems experience

Marketplace/platform/data-intensive

Strong quantitative fluency

Cross-functional influence

Written & verbal communication

Job description

The role

Headway is hiring Product Managers at the Senior, Staff, and Principal levels to own product areas end-to-end across four domains: Patient, Provider, Payer, and Platform. This role exists because the opportunity to apply AI across a complex, regulated, multi-sided marketplace is massive, and the company needs experienced product leaders who can set strategy, drive outcomes, and build with AI as a core part of the toolkit. Product Managers at Headway partner deeply with engineering, data science, design, clinical, and operations teams, and are accountable for moving the company forward in their area. The way Headway builds is continuously evolving, and these roles sit at the intersection of healthcare delivery, complex insurance systems, and a marketplace serving tens of thousands of providers and millions of patients.

What you would do

• You would define and own the product strategy for your area in partnership with engineering, design, data, clinical, and operations teams.
• You would identify where AI creates step-change improvements in your product area and drive those bets from initial insight through to production.
• You would set and own clear success metrics, communicate results to stakeholders, and course-correct with urgency when needed.
• You would represent the voice of your customer, whether that is a patient, a provider, or a health plan, grounding every decision in data and direct research.

Depending on which domain you join, the specific problems you would work on vary.

• On the Patient side, you would build AI-powered matching and personalized care navigation to help patients get into and stay in mental health care, working on systems that handle one million referral requests per month.
• On the Provider side, you would use AI to automate clinical workflows, simplify complex insurance requirements, and reduce the administrative burden on therapists so they can spend more time with patients.
• On the Payer side, you would build tools that measure clinical outcomes, demonstrate responsible care to health insurers, and support a model where patients are matched to the right care pathways.
• On the Platform side, you would work on the billing, claims, payments, and trust and safety infrastructure that underpins Headway, using AI to automate high-volume workflows, detect fraud and errors, and build systems that improve over time.

What they are looking for

• You would need at least eight years of product management experience with a track record of owning complex, high-impact product areas.
• Experience with LLM systems, including prompting, retrieval, evaluation, and fine-tuning, is required, along with a demonstrated history of shipping AI-powered products that hold up at scale rather than remaining at the demo stage.
• You would need experience building at scale in a marketplace, platform, or data-intensive environment, with clear outcomes you can speak to.
• Headway is looking for someone who is energised by working in regulated, complex industries and who treats constraints as a product design challenge rather than a blocker.
• You would need the ability to influence across engineering, clinical, legal, finance, and operations functions, and to be equally comfortable in the data and in the room with senior leadership.
• Strong quantitative fluency is required, including the ability to partner with data scientists on experiment design and causal analysis.
• Clear, precise communication in writing, in product reviews, and with senior leadership is also expected.

Working arrangements

This role is not described as requiring a specific office location. The listing does not specify remote, hybrid, or on-site requirements beyond the inclusion of a work-from-home stipend as a benefit, which suggests remote or flexible working is supported.

Pay and benefits

The expected base pay range for this position is $212,000 to $265,000, based on qualifications, experience, and geographic location.

The role may also be eligible for an equity grant depending on level.

Benefits include equity compensation, medical, dental, and vision coverage, HSA and FSA options, a 401K plan, a work-from-home stipend, therapy reimbursement, 16 weeks of parental leave for eligible employees, Carrot Fertility annual reimbursement and membership, 13 paid holidays per year plus a holiday break between December 25th and December 31st, flexible paid time off, an Employee Assistance Program, and training and professional development support.

• equity compensation
• medical
• dental
• vision coverage
• HSA and FSA options
• a 401K plan
• a work-from-home stipend
• therapy reimbursement
• 16 weeks of parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays per year plus a holiday break between December 25th and December 31st
• flexible paid time off
• an Employee Assistance Program
• training and professional development support