Senior IT Engineer (AI & Automation) at Headway

New York, New York, United States

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Not SpecifiedCompensation

Senior (5 to 8 years)Experience Level

Full TimeJob Type

UnknownVisa

Healthcare, Mental Health, HealthtechIndustries

Requirements

Architect, build, and deploy scalable workflow automations and integrations across core business systems using AI/LLMs and agentic automation
Design, build, and maintain custom internal tools leveraging APIs and cross-platform automation tools
Implement error handling and observability for automations and internal tools
Develop automation templates/standards and frameworks that enable future workflows to be created rapidly and with consistency
Develop testing frameworks for automated workflows to ensure quality, reliability, and resilience
Develop longitudinal relationships across Headway and partner with stakeholders to design and implement automated solutions to enable Headway teams to work with speed

Responsibilities

Use AI, LLMs, and agentic automation to solve meaningful operational problems across the company
Architect and ship scalable workflows while diving into new technologies such as AI
Build internal tools from scratch, not just configuring out-of-the-box features
Add observability, structured error handling, and testing frameworks so automations behave like production software
Create reusable frameworks, templates, and patterns so future workflows can be built faster and more consistently—not one-off scripts
Partner closely with internal teams to understand their needs and translate them into solutions that materially increase speed and efficiency
Design foundations that scale as the company grows, thinking in systems rather than tasks

Skills

LLMs

Agentic Automation

Automation

Productivity Engineering

Workflows

Scalable Systems

Headway

Connects patients with affordable mental health services

About Headway

Headway simplifies the process of finding and paying for mental health therapy. It operates in the mental health market, addressing the challenge that many Americans face in accessing care due to high costs and complicated insurance processes. For individuals, Headway provides a platform where they can easily search for therapists and psychiatrists who accept their insurance, allowing them to find the right mental health care without incurring out-of-pocket expenses. For mental health care providers, Headway reduces the administrative workload associated with accepting insurance, enabling them to focus more on patient care. The company connects patients with providers while ensuring effective use of insurance, and it generates revenue by partnering with health plans and providers. Headway's goal is to create a more accessible and affordable mental healthcare system.

New York City, New YorkHeadquarters

2019Year Founded

$318.1MTotal Funding

LATE_VCCompany Stage

HealthcareIndustries

1,001-5,000Employees

Benefits

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 Paid Time Off

Employee Assistance Program (EAP)

Training and professional development

Risks

Increased competition from platforms like BetterHelp and Talkspace.

Potential backlash from professionals feeling undervalued by Headway's platform.

Regulatory scrutiny as Headway expands into Medicare Advantage and Medicaid.

Differentiation

Headway simplifies finding and paying for therapy with an insurance-accepting provider network.

It reduces administrative burdens for mental health professionals, enhancing focus on patient care.

Headway's platform offers both virtual and in-person therapy sessions, increasing accessibility.

Upsides

Raised $100M in Series D to expand into Medicare Advantage and Medicaid.

Partnerships with Cigna and Blues plan to expand services to all 50 states.

Growing demand for telehealth services boosts Headway's market potential.

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