Head of Engineering

Assured is transforming the infrastructure of U.S. healthcare using intelligent automation.
We’re building the AI-powered workforce for the healthcare back-office - digital workers that reason, act, and automate complex administrative workflows, empowering healthcare organizations and operations teams around the country.

These processes cost the system billions of dollars each year, delay patient care, and keep clinicians from doing the work that matters.

We’re backed by top Silicon Valley investors and trusted by leading provider groups, digital health companies, and health systems. This is a rare opportunity to join an elite team reimagining one of the most broken parts of healthcare — using cutting-edge AI in production, at scale.

We’re looking for a Head of Engineering to architect, build, and scale the technical foundation of Assured. You’ll define our architecture, hire and mentor a world-class engineering team, and bring to life the next generation of our AI-powered digital workforce for healthcare.

This role is for someone who thrives in early-stage environments, values autonomy, and wants to own decisions end-to-end — from system design to hiring to culture.

You'll set the bar for technical excellence while moving fast to build real, production-grade systems.

System Architecture & Design

• Design and evolve a modular, service-oriented architecture to power configurable healthcare workflows at scale.

• Build a workflow orchestration engine capable of handling thousands of concurrent stateful tasks (credentialing, verification, enrollment).

• Define and optimize integration frameworks to connect with thousands of external systems — web portals, APIs, PDFs, spreadsheets.

• Drive reliability, auditability, and performance through observability, self-healing, and clear fault-domain boundaries.
  

Applied AI and Automation

• Lead the design and deployment of AI-powered digital workers — LLM- and rules-driven agents that perform operational workflows end-to-end.

• Evaluate AI tools, frameworks, and third-party APIs, ensuring alignment with platform goals and data protection requirements.
  

Technical Leadership & Team Building

• Recruit, mentor, and develop an exceptional engineering team in NYC.

• Establish engineering culture, values, and practices around velocity, accountability, and autonomy.

• Act as a hands-on leader: willing to dive into architecture, code, or design reviews when needed.

• Create clarity, empower ownership, and scale a high-agency culture that ships quickly.
  

Security, Compliance & Governance

• Champion best practices for system security, auditability, and privacy by design.

• Lead efforts in incident response readiness, chaos engineering, and platform reliability.
  

Collaboration & Stakeholder Engagement

• Partner closely with all other teams to translate real-world workflows into elegant, scalable systems.

• Represent engineering at the leadership level — influencing roadmap, prioritization, and long-term company direction.

Must-Have:

• 7+ years building and scaling complex, distributed systems or workflow-heavy SaaS platforms.

• Proven ability to own architecture and make high-stakes technical decisions in ambiguous, high-growth environments.

• Deep understanding of modern cloud architecture.

• Experience building or leading teams working with applied AI, automation, or data-intensive systems.

• Excellent communication — able to clearly explain technical trade-offs to technical and non-technical audiences alike.

• Demonstrated ability to recruit, lead, and inspire engineers — especially in competitive markets.

Nice-To-Have:

• Background in healthcare, insurance, or other regulated industries (finance, logistics).

• Experience with workflow orchestration frameworks or event-driven architectures.

• Contributions to open-source projects, publications, or active technical presence.

You’ll Love This Role If You

• Want to own architecture, team, and culture — not inherit them.

• Thrive in a 0→1 environment, building from scratch and scaling from concept to production.

• Care deeply about impact — accelerating patient access by fixing the infrastructure of healthcare.

• Believe great products emerge from tight collaboration between product, engineering, and operations.

• Want your work to outlast you — building systems that become part of healthcare’s invisible infrastructure.
  

• High-impact work – Eliminate bottlenecks that delay access to care.

• Real-world AI – Build intelligent systems that reason, act, and automate in production.

• Cross-functional exposure – Work closely with customers, clinical ops, and founders.

• Early-stage upside – Significant equity, influence, and high-growth trajectory.

• People-first culture – High autonomy, flexible hybrid model, outcomes > hours.