About the role

Join us to build the measurement and decision engine for patient growth.

As a Staff Data Scientist, Growth, you will be the senior analytical and strategic leader who makes marketing performance legible, credible, and actionable. You will partner closely with Growth Marketing leadership and channel owners across paid, lifecycle, and organic, plus Finance, Product, and Engineering. Your job is to help Headway answer the questions that matter:

• What is truly incremental?
• Where should we invest next?
• What is driving performance shifts?
• How do we scale what works without fooling ourselves?

You will build the frameworks, analyses, and modeling approaches that enable the marketing team to move faster with confidence. This is high-stakes decision support for a growth engine that needs to compound and certainly not a dashboard-only role or “just attribution” role. 

What you will do

• Own incrementality measurement across channels. Design and analyze geo tests, holdouts, lift tests, and quasi-experimental approaches when randomized tests are not feasible. Define clear guardrails, decision rules, and what “good” looks like.
• Build a marketing measurement system that leaders trust. Define canonical metrics (CAC, LTV, payback, conversion, retention, capacity-adjusted ROI), ensure definitions are consistent, and create a clear measurement narrative that aligns Marketing, Finance, and Product.
• Turn ambiguity into a plan. When performance changes, you will diagnose why, quantify contributing drivers, and recommend concrete actions. You will be the person who can say, “Here’s what moved, here’s why we believe it moved, and here’s what we do next.”
• Develop and evolve modeling approaches where they create leverage. Build practical models such as LTV and retention forecasting, cohort value prediction, causal uplift models for lifecycle, and marketing mix modeling when appropriate. Focus on models that survive contact with reality: calibration, backtesting, and decision usefulness.
• Partner with Engineering on the measurement plumbing. Improve event instrumentation, identity resolution assumptions, offline conversion integration, and data quality monitoring so measurement is robust. Advocate for minimal, decision-critical requirements that unlock reliable learning.
• Design learning loops that scale. Create repeatable experimentation and analysis templates for channel and creative testing, including measurement of message by audience by surface. Increase testing velocity without lowering the truth standard.
• Influence strategy, not just reporting. Bring an evidence-based point of view on channel allocation, growth constraints, saturation, diminishing returns, and the tradeoffs between short-term acquisition and long-term retention and care outcomes.
• Uplevel the team. Mentor analysts and data scientists working on growth, set quality standards, and help establish best practices across experimentation, causal inference, and forecasting.

What will make you successful

• 10+ years using data science, analytics, and experimentation to drive decisions in marketing, growth, or marketplace environments (or equivalent scope and demonstrated impact).
• Deep expertise in causal inference and incrementality in real-world marketing systems: you know the failure modes (selection bias, channel cannibalization, platform noise, attribution myths) and how to design around them.
• Strong SQL plus strong proficiency in Python or R, with the ability to build reliable, reusable analytical workflows.
• Practical modeling skill, especially as applied to marketing and growth: cohorting, forecasting, LTV estimation, saturation and diminishing returns, MMM concepts, calibration and monitoring.
• Track record of influencing executive decisions with clear recommendations and measurable outcomes, not just analysis.
• Excellent communication: you can make complex measurement logic understandable and defensible to non-technical partners, and you can call out uncertainty without losing momentum.
• High ownership and strong judgment: you prioritize what changes decisions, you move quickly, and you know when to slow down because the risk is real.
• You are motivated by the mission. Access and affordability in mental healthcare are not abstract problems here.

Nice to have

• Experience with geo experiments, marketplace constraints, or capacity-aware marketing optimization.
• Experience measuring acquisition quality beyond conversion: downstream engagement, retention, clinical matching quality, and unit economics.
• Familiarity with lifecycle marketing measurement (incrementality, uplift, experimentation design for messaging).
• Experience partnering with Finance on budget allocation, payback, and scenario planning.
• Comfort working with imperfect identity, privacy constraints, and evolving attribution ecosystems.

Compensation and Benefits:

The expected base pay range for this position is $212,000 - $265,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• 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 PTO
• Employee Assistance Program (EAP)
• Training and professional development

The Work

Fullstack at Headway means end-to-end ownership. You're building reliable abstraction layers over a fragmented healthcare system and translating them into seamless, empathetic user experiences. What you could work on:

• Therapist Practice Management: Build a best-in-class platform for Headway therapists to run their businesses. You'll own features from the database schema to the UI, creating intuitive web experiences for scheduling, AI-assisted clinical documentation, and payment management.
• Patient & Provider Engagement: Deepen the relationship between patients and their care. Build the interfaces and APIs that power seamless communication, personalized experiences, and tools that keep patients connected to their providers — and providers focused on what matters most.
• The Modern AI-Enabled Clinical System: Help design and build the systems that manage clinical data. Create high-integrity experiences for treatment plans and progress notes, integrating AI-powered clinical intelligence to give providers their time back.
• Frictionless Onboarding: Turn the historically painful process of insurance credentialing into a sleek, consumer-grade experience. Build products and tooling to get providers in-network and scaling their practice in record time.
• Growing the Network: Own the tools and experiences that expand Headway's reach — from acquiring new providers to empowering existing ones to bring their patients onto the platform. Build the infrastructure that fuels sustainable, high-quality growth.
• Technical foundations: Help the teams see around corners and lay the technical foundations for the future of our product. Build systems, tools, and processes that enable the team to ship innovative products quickly, safely, and reliably.
• Strategic leadership: As a Staff Engineer, you will work with a cross functional leadership team to shape the roadmap and technical strategy for the space.

#LI-BM1

About The Role

You will be the first dedicated AI Product Manager on the Patient side at Headway. Your mission: build AI-powered products that help patients find the right therapist, stay engaged in care, and achieve measurable improvements in their mental health.  This is not an AI-strategy-deck role. You will ship. You will write evals. You will debug prompt chains. You will partner with ML engineers and data scientists to build products that work for real patients in a HIPAA-compliant environment.  We power over 500,000 appointments per month. Now we are building AI-powered experiences to help patients find the right care and stay in it!

What you’ll do at Headway:

• Own AI-powered patient intake and therapist matching: design LLM-driven flows that understand patient needs and recommend the right provider.
• Build between-session AI support experiences: personalized tools that help patients reflect, prepare, and build therapeutic habits.
• Establish evaluation and safety infrastructure: write evals, build test suites, design red-teaming protocols, and implement human-in-the-loop escalation.
• Advance outcome measurement: move beyond PHQ-9/GAD-7 to AI-informed measurement.
• Partner with Engineering, ML, Data Science, Clinical, and Legal to ship AI products in a HIPAA-compliant architecture.

You’ll be great for this role if you:

• 8+ years of PM experience, with at least 2 years shipping AI/ML-powered products to real customers.
• You have personally written evals for AI product quality.
• You have built multi-step LLM-powered user flows in production.
• Strong technical fluency with LLMs: model selection, RAG architectures, fine-tuning, cost/latency/quality.
• You are a builder who has shipped AI products in partnership with ML engineers.
• Bonus: Experience in regulated industries (healthcare, fintech, insurance).
• Bonus: Experience in healthcare or mental health.
• You understand that building AI for people managing their mental health requires a different level of care and safety.

Compensation and Benefits:

The expected base pay range for this position is $212,000 - $265,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• 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 PTO
• Employee Assistance Program (EAP)
• Training and professional development

#LI-EM1

About Data Engineering at Headway 

Headway is looking for a Staff Data Engineer to help us get closer to executing our mission: to create access to affordable, quality mental healthcare across the United States. 

The Data Engineering Team is the foundational engine of our data-driven organization. We are a high-impact group of engineers focused on delivering reliable, high-quality data assets at enterprise scale. Our work is centered on transforming raw data into business-ready intelligence through robust ETL/ELT pipelines, advanced data modeling, and rigorous data quality frameworks. We operate with a strong engineering discipline, partnering closely with Data Scientists, Analysts, and core Software Engineering teams to ensure data is not just available, but completely trustworthy for every critical decision and product feature.

About this role

As a Staff Data Engineer, you will be a hands-on technical leader, architect, and mentor, responsible for defining the future state of our data infrastructure. This role focuses on setting architectural direction, establishing organization-wide data standards, and driving the design of highly scalable and optimized data models. You will lead complex, multi-functional initiatives, focusing on data quality governance and the maturity of our pipelines. You will be expected to influence our technology choices, mentor other engineers, and act as the primary technical interface between the Data Engineering team and senior stakeholders across the business.

You Will Love This Role If You Have: 

• 9+ years of experience in data engineering, with a proven track record of architecting and shipping progressively more complex, large-scale data products.
• Expert-level proficiency in our modern data stack, including Snowflake, dbt, Apache Airflow, and Python. You are capable of defining best practices and architectural patterns across these tools.
• Deep mastery of advanced data modeling techniques and their application within production systems to achieve high performance.
• Architectural Ownership: Proven ability to define the technical roadmap for the entire data platform, working horizontally to influence architectural decisions and technical debt management across multiple engineering teams.
• Engineering Elevation: A strong track record of mentoring, coaching, and elevating the technical skills, code quality, and engineering maturity of other data engineers.
• 2+ years of Marketplace Experience: Prior experience in the marketplace or two-sided platform is a significant plus.

Compensation & Benefits:

The expected base pay range for this position is $212,000 - $265,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• 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 PTO
• Employee Assistance Program (EAP)
• Training and professional development

Join us to build the truth engine behind better mental health outcomes.

As a Senior Staff Data Scientist, Bayesian Experimentation and Causal Inference, you will be the company-wide owner of how Headway learns from data, especially when the stakes are high and the signal is noisy. You will report directly to the Head of Data and serve as a core leader for standards, frameworks, and decision quality across Product, Growth, Ops, and Finance.

Your work will set the default methods for how we answer questions like:

• Did this actually cause the outcome we care about?
• How sure are we, and what should we do given that uncertainty?
• What evidence is strong enough to change strategy, policies, or spend?

A major objective of this role is to build and institutionalize a clear map of “what we know” about patients, providers, and payers, with explicit confidence levels that tie directly to business action. Think of it as a shared language that prevents the organization from treating a correlation like a law of physics, while still moving fast.

What you will do

• Own causal inference and experimentation standards across Headway. Define the canonical approaches, guardrails, documentation, and review mechanisms for experiments and quasi-experiments, including when and how to use Bayesian methods.
• Build the confidence ladder for company knowledge. Create a clear, shared framework that maps findings to levels of confidence (for example 1–10), where lower levels reflect correlation and early directional evidence, mid levels reflect increasingly credible causal inference, and the highest levels reflect stable, repeatable, decision-grade truths. Operationalize it so it shows up in artifacts teams actually use: PRDs, launch reviews, growth planning, quarterly business reviews, and postmortems.
• Design the learning strategy for our hardest questions. Lead the approach for ambiguous, high impact domains like provider activation and retention, payer economics and policies, patient conversion and engagement, and marketplace dynamics. Recommend the right combination of randomized experiments, stepped rollouts, geo tests, natural experiments, and observational designs.
• Raise the organization’s statistical maturity. Introduce and standardize Bayesian experimentation practices where it improves speed and decision quality (priors, posterior interpretation, sequential decision rules, credible intervals, expected value framing). Build training, playbooks, and reusable tooling.
• Be the escalation point for difficult measurement problems. Tackle issues like interference and spillovers, network effects, selection bias, noncompliance, measurement error, multiple comparisons, seasonality, and Simpson’s paradox showing up in real life and causing confusion.
• Partner with Data Platform and Engineering to make rigor scalable. Ensure experimentation and inference are supported by instrumentation, logging, metric definitions, semantic layers, and monitoring. Help define the minimal foundations required for trustworthy learning.
• Build a culture of clear claims. Establish norms for separating facts, estimates, assumptions, and uncertainties. Make it easy for teams to say “we do not know yet” without losing momentum, and easy for leaders to understand what is safe to act on.
• Mentor and set the bar. Coach other data scientists and analytics leaders. Create review standards for causal work, support hiring for methodological depth, and represent Headway’s measurement philosophy internally and externally when appropriate.

What will make you successful

• 12+ years of experience applying causal inference, experimentation, and advanced statistics to real-world product, growth, or operational decisions (or equivalent depth demonstrated through scope and outcomes).
• Deep expertise in causal inference across randomized and observational settings, including practical strategy for when clean experiments are not possible.
• Deep expertise in Bayesian methods for experimentation and decision-making, and strong judgment about when Bayesian approaches outperform frequentist defaults and when they do not.
• Strong SQL and strong proficiency in Python or R, including building reusable analysis tools and improving team workflows.
• Track record of setting org-wide standards that materially improved decision quality and execution velocity.
• Executive-level communication and influence: you can drive alignment across Product, Growth, Ops, Finance, and Engineering.
• Comfort operating in ambiguity, and the ability to turn it into crisp frameworks, clear recommendations, and measurable outcomes.
• Motivation for our mission: improving access and affordability in mental healthcare.

Nice to have

• Experience in marketplaces, healthcare, insurance, or other regulated and complex incentive systems.
• Experience with experimentation under interference and network effects.
• Experience building experimentation platforms, analysis libraries, or statistical tooling used broadly across an organization.
• Familiarity with causal graphs, uplift modeling, and decision theory framing (expected value, value of information).

Compensation and Benefits:

The expected base pay range for this position is $249,600 - $312,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• 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 PTO
• Employee Assistance Program (EAP)
• Training and professional development

#LI-MG1

About the role

Join us to build the decision engine for better mental health outcomes.

As a Staff Data Scientist, Product Analytics, you will be a senior technical and strategic leader for how Headway measures, learns, and improves. You will own the hardest and most ambiguous product questions, shape how we define success, and drive decisions that cut across multiple teams and product surfaces. You will not only run the analyses, you will influence what we build, how we evaluate it, and how we scale what works.

This role is for someone who can zoom in to debug a metric definition and zoom out to design a measurement strategy for a major product area, then bring the organization along with them.

What you will do

Everything in the Senior role, plus:

• Own a product measurement strategy. Define north star and input metrics for a major product area (or multiple surfaces), align stakeholders on definitions, and build conviction in what “good” looks like.
• Lead multi-team initiatives. Drive cross-functional work where the right answer is not obvious and the path is not linear, and ensure we land measurable outcomes.
• Set the experimentation standard. Establish frameworks for test design, guardrails, decision rules, and interpretation that improve both speed and rigor across teams.
• Develop evaluation systems for complex products. For areas like matching, ranking, or applied AI experiences, build measurement approaches that combine offline evaluation, online experiments, and human-quality signals when needed.
• Build scalable analytical assets. Invest in durable measurement systems: semantic definitions, self-serve dashboards, monitoring and alerts, and repeatable templates that reduce ad hoc work.
• Mentor and uplevel. Coach other data scientists and analytics partners, provide strong technical review, and model what great looks like.
• Be a thought leader. Proactively identify opportunities, shape roadmaps with an evidence-based POV, and create clarity where teams feel stuck.

What will make you successful

• 10+ years using data to drive product or business decisions in product, growth, engineering, or operations environments (or equivalent depth of experience and scope).
• Expert fluency in SQL and strong proficiency in Python or R, including building reliable, reusable analysis workflows.
• Deep expertise in Bayesian experimentation, causal inference, and measurement design, including common failure modes and how to prevent them.
• Strong applied modeling judgment: you know when a model is the right tool, and you can build, validate, and launch responsibly.
• A track record of leading ambiguous, cross-team work and delivering measurable outcomes (not just insights).
• Excellent executive communication and influence: you earn trust, align stakeholders, and move decisions forward.
• Strong product sense and an instinct for decision leverage: you focus on what changes outcomes, not what is merely interesting.
• Motivation for our mission: improving access and affordability in mental healthcare.

Compensation and Benefits:

The expected base pay range for this position is $212,000 - $265,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• 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 PTO
• Employee Assistance Program (EAP)
• Training and professional development

#LI-MG1

About the role:

We're seeking a Senior Product Manager to lead our Provider Acquisition pod. Your mission will be to drive sustainable user acquisition and revenue growth through data-driven search marketing strategies and product optimizations. You'll partner with Engineering, Marketing, Data, and Design to build scalable growth systems that maximize our search visibility and conversion funnel performance. The ideal candidate thrives in a metrics-driven environment, has expertise in search marketing, and is passionate about leveraging product innovation to accelerate growth.

What you’ll do at Headway:

• Develop and execute a comprehensive growth strategy that leverages SEO, SEM, and product to drive provider acquisition, engagement, and retention.
• Partner with engineering and data science teams to implement features, landing pages, and experiences that improve our ability to find and acquire new providers across multiple segments 
• Collaborate with content and marketing teams to align SEO content strategy with product roadmap and business objectives.
• Design, launch, and optimize referral programs, invite flows, and affiliate networks to accelerate acquisition

You’ll be great for this role if you:

• Bring growth experience: You have 5+ years of product management experience with demonstrated success in growth-focused roles, ideally with SEO and SEM expertise, and the proven ability to drive measurable results.
• Are data and results driven: You love running experiments and are a master at digging into data, defining clear goals, running toward them & bringing your team along the way.
• Are highly collaborative: You work well with other functions and teams and can collaborate on delivering impact together to a shared goal. 
• Thrive in ambiguity: You love tackling ambiguous problems in a fast-paced environment with an optimistic and energizing attitude.

Compensation and Benefits:

The expected base pay range for this position is $180,000 - $225,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• 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 PTO
• Employee Assistance Program (EAP)
• Training and professional development

#LI-EM1