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About engineering at Headway

Building a new mental healthcare system at Headway is only possible because of the scale and leverage that software can provide. The engineering team at Headway is a small but mighty team using technology to build that future (and have a fun time while doing it!).

Principles that guide us:

• Focus on the mission: We view software as a means of effecting change in the world, not as an end unto itself. We write software to empower our patients and therapists to better solve the problems they’re facing.
• Ship small, learn fast: We are building new and novel products and believe that we learn what our users need by quickly shipping and iteration
• Everything is a product: Whether it's our patient search experience or a developer productivity improvement, we treat everything we build at Headway as a product with end-users in mind.
• Optimize for trust: We believe that engineers should be continually learning. To learn effectively and to be productive, engineers must feel safe asking questions and discussing mistakes.

Tools we use:

• Languages: Python 3, TypeScript
• Libraries & Frameworks: FastAPI, React, Remix, Next.js, React Aria
• Infrastructure: AWS (Fargate, ECS, S3, and more), Spark and Kafka
• Monitoring: Datadog, PagerDuty, Sentry
• Version Control: Github, PagerDuty

About the role:

We are looking for a Staff AI Engineer to lead how we design, build, and operate AI powered systems within the patient experience. This role will help establish Headway’s approach to AI engineering by creating strong tooling, evaluation frameworks, and development practices. At the same time, it will directly own and deliver our earliest AI supported patient products, including AI assisted intake and AI supported therapy experiences.

This is a hands on technical leadership role. You will write production code, design systems that multiple teams rely on, and partner closely with product, clinical, and data leaders to ensure that our AI systems are safe, effective, and aligned with patient outcomes.

Who you are

We are looking for a Staff level engineer who thrives in ambiguity and is excited to learn new technologies and systems. You care about building high impact products, you think in systems, and you raise the bar for the people around you.

• You shape technical work to achieve company and team goals, not just local optimizations.
• You are willing to flex into new technical and non technical areas as projects require.
• You have driven technical vision and strategy at the organizational level through technical design documents, reviews, and participation in planning cycles.
• You have led major technical initiatives that required coordination across multiple teams and stakeholders.
• You regularly mentor senior engineers and technical leaders and help set technical direction through influence rather than authority.
• You have real world experience building AI powered features using LLMs or applied machine learning.
• You have designed evaluation strategies for AI systems and understand the limits of automated metrics, especially in domains where correctness, safety, and tone matter.
• You care deeply about reliability, privacy, and safety when deploying AI systems and you design with these constraints in mind from the start.
• You are comfortable partnering with product managers, designers, clinicians, and legal or compliance partners to translate complex domain needs into responsible AI systems.

Our interview process

After you apply to Headway, here are some details of what to expect during the interview process.

Initial screen: You’ll connect with someone in recruiting so you can learn more about the team, Headway’s mission and exciting growth, and we can get a better idea of your background.

First round: You'll meet with an engineer on the team to do some live coding and learn more about the engineering team.

Final rounds: You’ll meet several more team members for technical and non-technical interviews and leave with a fuller picture of what it’s like to work at Headway.

References and the Offer: Our favorite part of the process! We'll send over all of the details, including specifics on employee equity, and congratulatory messages from excited future team members!

Compensation and Benefits:

The expected base pay range for this position is $224,000 - $280,000, 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

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