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Headway

Headway

New York, NY

Insurance-enabled platform matching patients to mental health providers

58 open roles
Health Tech201-1000Series D+Founded 2019Salary transparent

About

Headway builds software to connect patients with in-network therapists and psychiatrists who accept insurance, handling credentialing, billing, and claims. It serves patients seeking affordable mental health care and providers aiming to grow practices without administrative burdens. This addresses access barriers where most therapists don't accept insurance, enabling millions to get timely care.

Tech stack

PythonSQLRAWSTypeScriptFastAPIdbtReactPostgresRedisNext.jsKafkaSQLAlchemySnowflakeDatadog

Perks & benefits

Health insuranceDental insuranceVision insurance401kUnlimited PTOParental leaveEquityHome office stipend

Open roles

58
Headway

Senior Product Designer, Client Management

HeadwayNew York, NY +2

Lead product design for Headway’s provider-facing calendar, scheduling, messaging, and client management experiences. The role requires 5+ years of product design experience, strong systems and interaction craft, cross-functional collaboration, and comfort prototyping with AI tools.

180k – 225k/yrHybrid5+ YOEProduct Design
Headway

People Operations Manager

HeadwayUnited States

Build and scale HR operations infrastructure, including AI-powered workflows, manager enablement tools, employee-process automations, and people analytics dashboards. The role requires hands-on experience with HR operations, AI tooling, data systems, and cross-functional program management.

114k – 179k/yrRemote5+ YOEPeople Ops
Headway

Senior Product Designer, Provider Acquisition

HeadwayNew York, NY +2

Design provider acquisition experiences across public-facing landing pages, lead forms, and internal agentic tooling. The role requires 5+ years of product design experience, strong visual and interaction craft, funnel optimization expertise, and experience with AI-powered workflows.

180k – 225k/yrHybrid5+ YOEProduct Design
Headway

Staff Product Designer, Provider CRM & Prospect Management

HeadwayNew York, NY +2

Leads 0-to-1 product design for a provider CRM and AI front-desk and scheduling assistant, shaping prospect pipelines, automation behaviors, and multi-actor workflows. Requires 8+ years of product design experience, CRM or operational product expertise, strong craft, and comfort prototyping with AI tools.

212k – 265k/yrHybrid8+ YOEProduct Design
Headway

Manager, Revenue Accounting

HeadwayUnited States

Leads revenue accounting operations, ensuring ASC 606 compliance, month-end close, and process improvements while managing a team of accountants. Partners cross-functionally in a high-growth environment; requires 5-7+ years experience, CPA, and leadership skills.

110k – 173k/yrRemote5+ YOEFinance & Accounting
Headway

Contract Technical Recruiter

HeadwayUnited States

Contract Technical Recruiter partnering with engineering leaders to run full-cycle searches, build high-quality technical pipelines, and close top engineering talent for Headway's mental healthcare platform. Requires 3+ years full-cycle recruiting experience in high-growth tech environments.

166k – 208k/yrRemote3+ YOERecruiting
Headway

Senior Counsel, Product

HeadwayNew York, NY +1

Senior product counsel partnering with R&D teams at a mental healthcare platform. Provide real-time regulatory guidance on AI, data use, and health tech laws to enable innovation while managing risk. Requires 5-7+ years healthcare regulatory experience and ability to translate complex rules for engineering and product teams.

179k – 280k/yrRemote5+ YOELegal
Headway

Staff Data Scientist

HeadwaySan Francisco, CA +2

Own commercial data science end-to-end for Headway's GTM and payer business. Lead strategic analyses, forecasting, and causal inference for the Chief Commercial Officer and executive stakeholders while technically leading other data scientists.

212k – 265k/yrHybrid10+ YOEData Science
Headway

Senior Manager, Data Science, Provider Experience

HeadwayNew York, NY +2

Lead and grow a data science team to drive insights, experimentation, and predictive modeling that improve provider experience metrics and product engagement at Headway. Requires 8+ years data science experience including 3+ years managing teams, strong product and cross-functional partnership skills, and technical fluency in SQL, Python/R, and causal inference.

212k – 265k/yrHybrid8+ YOEData Science
Headway

Senior Business Development Associate, Payer Partnerships

HeadwayNew York, NY

Senior Business Development Associate driving Headway's payer partnerships by owning external relationships, market analysis, deal content, and negotiations with health plans to expand access to mental healthcare. Requires 3+ years owning client-facing BD/sales cycles, commercial instinct, and fluent AI tool usage.

90k – 133k/yrRemote3+ YOEBusiness Development
Headway

FP&A Manager

HeadwayNew York, NY +1

FP&A Manager partnering with department leaders (CX, R&D, People, G&A) at high-growth mental health platform Headway to own financial strategy, lead deep-dive analyses, drive annual/long-range planning, and apply AI for insights as the company scales toward $1B revenue. Requires 6+ years blending IB/consulting/PE with strategic finance, strong modeling and communication skills.

152k – 200k/yrHybrid6+ YOEFinance & Accounting
Headway

Director, Payer Marketing

HeadwayUnited States

Build and lead Headway's Payer Marketing function from the ground up as a player-coach. Own payer positioning, narrative, GTM strategy, category story, clinical proof points, field enablement, and competitive intelligence to drive deeper payer relationships, renewals, expanded partnerships, and new revenue in behavioral health.

226k – 282k/yrRemote10+ YOEProduct Marketing
Headway

Program Manager, Talent & AI Enablement

HeadwayUnited States

Build and own end-to-end AI-powered enablement programs for Headway's Talent Acquisition team, including hiring manager training, employee referral redesign, recruiter skill development, and scaling agentic AI workflows across recruiting tasks while defining KPIs and ensuring responsible AI use.

115k – 179k/yrRemoteTechnical Program Management
Headway

Lead Brand & Creative Strategist

HeadwayUnited States

Lead the development of Headway's first comprehensive brand strategy and creative direction to make mental healthcare a household name. Define positioning, narrative, voice and visual identity; drive campaign creative strategy; build scalable brand systems and guidelines; and steward the brand internally across the organization. Requires 10+ years building trusted brands in complex or regulated industries.

225k – 282k/yrRemote10+ YOEBrand Design
Headway

Sr. Technical Recruiter

HeadwaySan Francisco, CA +2

Senior Technical Recruiter partnering with Engineering leaders at Headway to run full-cycle searches, build high-quality pipelines, advise on hiring strategy, and deliver exceptional candidate experiences in a high-growth environment.

121k – 190k/yrRemote5+ YOERecruiting
Headway

Senior Security Engineer

HeadwayNew York, NY +2

Senior Security Engineer partnering with product and engineering teams to design and implement secure features, build AI-native/agentic security tooling, create developer guardrails, and handle security operations at a mental healthcare platform company. Requires 5+ years in security/software engineering, strong technical depth, and excitement about AI in security.

223k – 279k/yrHybrid5+ YOESecurity Engineering
Headway

Senior Operations Associate

HeadwayUnited States

Senior Operations Associate responsible for building, executing, and scaling core operational workflows and processes at Headway to support mental healthcare providers and patients. Requires 3-5 years in consulting/ops/IB, strong data analysis, and systems thinking to drive efficiency, automation, and cross-functional initiatives with product and engineering teams.

76k – 112k/yrRemote3+ YOEBusiness Operations
Headway

Senior Data Scientist

HeadwayNew York, NY +2

Senior Data Scientist embedded in a product pod to design experiments, run causal analyses, and build predictive models that improve mental healthcare outcomes. Requires 6+ years driving product decisions with strong SQL/Python or R skills.

180k – 255k/yrHybrid6+ YOEData Science
Headway

Staff Technical Program Manager

HeadwayUnited States

Lead high-impact technical programs for the Insurance platform as the sole TPM, driving cross-functional execution, data rearchitecture, and operational improvements that deliver business-critical outcomes.

190k – 238k/yrRemote7+ YOETechnical Program Management
Headway

Senior Manager, Accounting

HeadwayUnited States

Lead day-to-day accounting operations and a team of four accountants, owning month-end close, financial reporting, and technical accounting under US GAAP while driving automation and process improvements.

131k – 204k/yrRemote10+ YOEFinance & Accounting
Headway

Staff Product Manager, AI Patient Experience

HeadwayNew York, NY +2

First AI PM on the patient side building LLM-powered products for therapist matching, between-session support, and outcome tracking in a HIPAA-compliant environment.

265k – 332k/yrRemote8+ YOEProduct Management
Headway

Applied AI Lead, Rev Ops

HeadwayUnited States

Lead AI-native revenue operations by building and shipping AI-powered workflows that automate GTM motions and drive scalable growth. Requires 5+ years in RevOps/Strategy and strong fluency with AI tools, SQL, and cross-functional project leadership.

121k – 190k/yrRemote5+ YOERevenue Operations
Headway

Staff Product Manager, AI Platform

HeadwayNew York, NY

Own Headway's AI platform vision and roadmap as the first AI Platform PM. Build and scale an ecosystem of agents, skills, and integrations (starting with Eddy) to make every employee AI-native.

265k – 332k/yrRemote8+ YOEProduct Management
Headway

Senior IT Engineer

HeadwayNew York, NY +2

Senior IT Engineer focused on designing and automating IAM lifecycle, IdP integrations, and RBAC initiatives for a fast-growing SaaS company. Requires 5+ years of IAM experience with Okta and strong stakeholder collaboration skills.

180k – 225k/yrRemote5+ YOEIT Support
Headway

Principal Product Manager

HeadwayUnited States

Lead high-stakes product domains end-to-end at a Series D mental health platform. Define strategy, ship AI-powered products, and drive alignment across engineering, clinical, and executive teams.

300k – 375k/yrRemote10+ YOEProduct Management
Headway

Staff Product Manager, Pricing

HeadwayNew York, NY +2

Own strategy and roadmap for core insurance platform covering claims processing, benefits verification, and payment disbursement. Drive technical decisions, build internal tools, and improve end-to-end customer journeys for providers and patients.

265k – 332k/yrHybrid7+ YOEProduct Management
Headway

Staff Data Infrastructure Engineer

HeadwayNew York, NY +2

Staff-level Data Infrastructure Engineer to architect and evolve the data platform (Snowflake, ingestion, orchestration, CI/CD, AWS infra) serving analytics, product, and ML teams. Requires 10+ years building scalable data platforms and proven technical leadership.

212k – 265k/yrHybrid10+ YOEData Engineering
Headway

Senior Manager, Data Engineering

HeadwayNew York, NY +2

Lead and scale Headway's data engineering team, owning architecture for data warehouse, pipelines, dbt transformations, and orchestration to power analytics, ML, and operations. Requires 8+ years data engineering experience and 3+ years managing teams.

212k – 265k/yrHybrid8+ YOEData Engineering
Headway

Staff Software Engineer

HeadwayNew York, NY

Staff-level engineer building LLM/ML systems for clinical documentation review, risk detection in healthcare claims, and provider-patient matching at a mental healthcare platform.

264k – 330k/yrRemote7+ YOEML Engineering
Headway

Director of Procurement

HeadwayUnited States

Director-level role building and owning Headway's procurement function from scratch. Lead strategic sourcing, vendor lifecycle management, cost optimization, and procurement tooling across SaaS, AI, cloud, and professional services spend.

200k – 265k/yrRemote8+ YOEBusiness Operations
Headway

Senior Product Designer, New Channels

HeadwayNew York, NY +2

Senior Product Designer owning patient experience across Health Systems, EAP, and Payer partnership channels. Designs referral-to-booking flows, runs multi-sprint experiments, and works in an AI-native design environment using Claude, Cursor, and MagicPatterns.

180k – 225k/yrHybrid5+ YOEProduct Design
Headway

Staff Backend Software Engineer

HeadwayUnited States

Staff Backend Engineer on the Revenue Engine team setting technical direction for payment and clearinghouse platforms. Hands-on leader designing fault-tolerant integrations with Stripe, Plaid, and payer systems while mentoring engineers.

224k – 280k/yrRemote7+ YOEBackend Engineering
Headway

Engineering Manager

HeadwayNew York, NY

Lead an engineering team building critical insurance platform infrastructure at Headway. Own technical direction, hiring, and cross-functional coordination for systems handling payer communication, benefits, and claims.

190k – 238k/yrOn-site5+ YOEEngineering Management
Headway

Business Operations Lead

HeadwayUnited States

The Business Operations Lead will drive complex, cross-functional initiatives, build scalable workflows, and leverage data to inform decisions. This role requires strong problem-solving skills and a builder's mindset to improve efficiency and reliability.

105k – 155k/yrRemote5+ YOEBusiness Operations
Headway

Growth Associate, Care Partnerships

HeadwayNew York, NY

Drive high-volume cold outbound to book meetings with health system care leaders, building pipeline for the Care Partnerships BD team. Requires 1+ year of SDR/BDR experience and strong cold-calling skills.

77k – 77k/yrOn-site1+ YOESales Development
Headway

Associate Medical Director, Payer Partnerships

HeadwayUnited States

Psychiatrist or Clinical Psychologist supporting payer partnerships, driving data analyses on patient outcomes, and expanding provider network impact at a behavioral health tech platform.

211k – 330k/yrRemote5+ YOEOther
Headway

Associate Principal, Partner Success (Care Partnerships)

HeadwayUnited States

Manage and grow strategic partnerships with health systems and care providers, ensuring partner satisfaction while identifying expansion opportunities through data insights and cross-functional collaboration.

120k – 190k/yrRemote7+ YOEAccount Management
Headway

Senior Fullstack Software Engineer

HeadwayNew York, NY +2

Senior Fullstack Software Engineer building end-to-end features for a mental healthcare platform used by 75,000+ providers. Owns product features from database to UI across clinical systems, practice management, patient experiences, and onboarding using TypeScript, Python, React, and AWS.

168k – 238k/yrHybrid5+ YOEFullstack Engineering
Headway

Senior Governance, Risk, Compliance (GRC) Analyst

HeadwayNew York, NY +2

Builds and matures GRC program supporting audits (HITRUST, SOC 2, PCI-DSS, HIPAA), manages vendor risk, security training, and technical risk register. Requires 5+ years GRC experience and knowledge of compliance frameworks.

162k – 202k/yrRemote5+ YOESecurity Engineering
Headway

Strategic Finance Manager

HeadwayNew York, NY +1

Strategic Finance Manager partners with GTM teams to model provider/patient economics, track churn/retention metrics, build dashboards, and drive cross-functional decisions for marketplace growth. Requires 6+ years experience, advanced Google Sheets/Looker proficiency, and AI enthusiasm.

152k – 190k/yrRemote6+ YOEFinance & Accounting
Headway

Director of Product, CX Product

HeadwayNew York, NY +2

Leads product vision and team for customer experience platform, building AI-powered self-service, proactive engagement, unified channels, and agent tools to cut costs and boost satisfaction. Requires 8+ years product leadership with CX/AI experience managing PMs.

250k – 312k/yrHybrid8+ YOEProduct Management
Headway

Staff Product Manager

HeadwayNew York, NY +2

Staff Product Manager owns end-to-end product strategy across Patient, Provider, Payer, or Platform areas at a mental health platform. Leverages AI (LLMs, prompting, fine-tuning) for matching, workflows, outcomes, and infrastructure in a regulated marketplace. Requires 8+ years PM experience shipping scalable AI products.

212k – 265k/yrRemote8+ YOEProduct Management
Headway

Associate Principal, Payer Partnerships

HeadwayUnited States

Owns commercial relationships and channel strategy with a national health plan partner to expand Headway's mental health footprint. Requires 7+ years in healthcare business development or partnerships, with expertise in building strategic relationships in complex organizations.

130k – 200k/yrRemote7+ YOEPartnerships
Headway

Staff Product Designer, Provider Onboarding

HeadwayNew York, NY +2

Leads redesign of AI-agent-powered provider onboarding experience to boost conversion from interest to first appointment, partnering with PM and Eng. Requires 8+ years product design with AI tools, funnel optimization, and strong craft in interaction/visual design.

212k – 265k/yrRemote8+ YOEProduct Design
Headway

Strategic Finance Lead, GTM

HeadwayUnited States

Leads strategic finance for GTM initiatives by building financial models, owning budgeting/forecasting, analyzing KPIs and unit economics, and providing cross-functional insights to optimize resource allocation and scale growth investments. Requires 4+ years experience, proficiency in Google Sheets/Looker, and AI enthusiasm.

132k – 160k/yrRemote4+ YOEFinance & Accounting
Headway

Senior Counsel, Regulatory

HeadwayNew York, NY

Provides strategic regulatory legal guidance to Clinical and Operations teams on healthcare laws, telehealth, and product development. Requires 5+ years healthcare regulatory experience, JD, and ability to translate complex regulations into actionable business advice.

179k – 280k/yrRemote5+ YOELegal
Headway

Director of Data Science - Patient

HeadwayNew York, NY +2

Leads data science team focused on patient acquisition, growth, marketing analytics, and product experimentation to drive consumer brand success and measurable patient impact. Requires 10+ years experience including team leadership and expertise in causal methods.

250k – 312k/yrRemote10+ YOEData Analytics
Headway

Staff Data Scientist - Finance & Accounting

HeadwayNew York, NY

Staff Data Scientist driving financial insights, metrics frameworks, forecasting, and GAAP-compliant reporting for Headway's revenue infrastructure and RCM systems.

212k – 265k/yrOn-site10+ YOEData Science
Headway

Account Executive

HeadwayNew York, NY +17

Drive growth by selling to therapists and psychiatrists via full-cycle sales, expanding Headway's provider network. Requires 1-3 years consultative sales experience, strong communication, analytical mindset, and resilience in a fast-paced startup.

69k – 77k/yrRemote1+ YOEAccount Executive
Headway

Staff Data Engineer

HeadwayNew York, NY +2

Staff Data Engineer architects scalable data infrastructure, leads ETL/ELT pipelines and data modeling using Snowflake, dbt, Airflow, and Python. Requires 9+ years experience, mentoring skills, and marketplace background.

212k – 265k/yrRemote9+ YOEData Engineering