Senior IT Engineer (AI & Automation) at Headway

New York, New York, United States

Headway Logo
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

Key technologies and capabilities for this role

AILLMsAgentic AutomationAutomationProductivity EngineeringWorkflowsScalable Systems

Questions & Answers

Common questions about this position

What skills are required for the Senior IT Engineer role?

Key skills include architecting and deploying scalable workflow automations using AI/LLMs and agentic automation, designing and maintaining custom internal tools with APIs, and implementing error handling and observability for automations.

What is the salary or compensation for this position?

This information is not specified in the job description.

Is this role remote or does it require office work?

This information is not specified in the job description.

What is the company culture like at Headway?

Headway emphasizes building meaningful career experiences, fostering operational efficiency through software, and creating scalable systems to reshape mental healthcare, with a collaborative approach partnering closely with internal teams.

What makes a strong candidate for this role?

Strong candidates enjoy using AI, LLMs, and agentic automation for operational problems, architecting scalable workflows, building custom internal tools from scratch, ensuring reliability with observability and testing, and thinking in 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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