Fractional Chief Operating Officer Jobs in Ridgefield, CT

Full Stack AI Engineer
TouchCare | Stamford, CT

About TouchCare

Every year, millions of Americans are overcharged, denied coverage they are entitled to, or simply give up on care they need because the system is too confusing to navigate. TouchCare exists to change that.

For over a decade, we've provided 1.4M+ members with a dedicated healthcare concierge — a real person backed by smart technology who resolves billing disputes, coordinates care, and fights on behalf of members when the system works against them. We're profitable, we're growing, and the problem we're solving is only getting more urgent.

The Role

The Applied AI Engineer will be our first internal full stack engineer, with a clear focus on reinvigorating our tech stack. You will build and maintain TouchCare's platforms, architecture, and systems in a HIPAA-regulated environment, working across the full stack to ship production-quality software that directly supports users and support team.

You'll report directly to the COO and work closely with the team to build an infrastructure that supports AI-driven solutions. You'll also partner with our global technology consultancy (8–9 engineers) who manage core infrastructure and compliance operations; your focus is what we build next on top of that foundation.

The Opportunity

We're making a significant investment in AI — and we're hiring our first internal AI engineer to implement it.

You'll work directly with the COO on innovative approaches: to identify where AI can make our member and employer experience higher quality, more efficient and effective.

The foundation is already strong: over a million members, a decade of healthcare navigation and claims data, and operational depth that takes most startups years to develop. The opportunity is to rebuild core workflows around what AI actually makes possible and to do it with real users in production from day one.

• This is a hands-on, production-focused role: you'll design, ship, and maintain the tech stack used by members and care advocates every day, not hypothetical users.

What You'll Build

• Autonomous Healthcare Navigation Agents
  Design and ship agentic workflows that handle complex, multi-step healthcare processes, claim triage, benefits navigation, billing resolution with minimal human intervention. You'll define the architecture, choose the tooling, and own these systems from prototype to production in a HIPAA-compliant environment.
• Internal Ticketing & Messaging Platform
  Build a purpose-built internal platform that gives our member services team a unified, intelligent workspace with routing, context surfacing, and asynchronous messaging designed for the way our team works. This includes integrating with healthcare and benefits systems, surfacing plan details and claims context, and ensuring auditability.
• AI Infrastructure & Evaluation Tooling
  Develop the frameworks that keep AI systems reliable and safe in healthcare: human-in-the-loop escalation paths and observability tooling that gives you a clear picture of system performance in production. You'll help define how we monitor PHI flows, safeguard member data, and continuously evaluate quality in a regulated setting.

What You'll Do

• Own full-stack feature development end-to-end: architecture, design, implementation, deployment, and iteration.
• Design and ship production AI agents and workflow automations that our member services and benefits advocacy teams depend on daily.
• Collaborate directly with the COO, operations, and member services teams to understand the healthcare and benefits workflows you're improving (claims, coverage issues, billing disputes, provider coordination).
• Build in a HIPAA-regulated environment.
• Partner with our external engineering team to maintain and improve existing systems, while helping migrate and streamline the tech stack over time.

Our Stack

• Languages & Frameworks
  Python · React · TypeScript · PostgreSQL
• Infrastructure & CI/CD
  GCP · GitLab · Jenkins
• Observability & Quality
  Sentry · Gurock TestRail
• Project Management & Collaboration
  Atlassian (Jira · Confluence)
• AI & Integrations
  LLM orchestration frameworks (LangChain / LlamaIndex or equivalent) · ElevenLabs (voice agents) · RESTful APIs · HIPAA-compliant infrastructure

You're a Strong Fit If You Have

• 3–6 years of software engineering experience, with meaningful time spent building and maintaining production system
• Full-stack engineering capability, comfortable owning frontend and backend across the full development lifecycle.
• Hands-on production experience, you've shipped systems real users depend on and iterated on them based on what you learned.
• Experience in a regulated environment, HIPAA, SOC 2, PCI, or equivalent
• Background in healthcare tech, benefits advocacy, carrier systems, or claims data, or a strong interest and willingness to go deep on this domain.
• An AI-native workflow, Cursor, Claude, GPT (or equivalents) are part of how you work every day, and you have developed opinions about when and how to use them effectively.
• Comfort operating as an individual contributor with engineering lead responsibilities, making technical decisions, collaborating with external partners, and owning outcomes without layers of process.

Bonus Points For

• Direct experience with healthcare navigation, employer benefits, or advocacy products.
• Startup experience, or a track record of shipping quickly inside a larger org while maintaining quality and compliance.
• Experience modernizing or migrating legacy infrastructure in production.
• Familiarity with asynchronous messaging platforms or customer service tooling (e.g., internal ticketing, contact centers, support platforms).

What We Offer

• Competitive base salary commensurate with experience
• Opportunity to build and shape company culture from day one
• Direct impact on improving financial wellness for thousands of employees
• Flexible and comprehensive benefits package

Why Join Us?

• Impactful Growth: Lead the technological expansion of specialized services that provide critical support to members during complex life events.
• Collaborative Environment: Work closely with a supportive team across Sales, Client Success, Product, and Marketing.
• Strategic Leadership: Shape the go-to-market strategy and future evolution of TouchCare's specialized portfolio.

Compensation: The salary range for this role is $150,000–$180,000, based on experience, skills, qualifications, and alignment with the scope of the role.

Benefits: TouchCare offers a competitive benefits package, including medical, dental, vision, paid time off, parental leave, and other company-sponsored benefits.

Location & Work Environment: This role is based at our Stamford, CT headquarters and is expected to be onsite 5 days per week.

TouchCare is an Equal Opportunity Employer. We are committed to building a diverse and inclusive workplace and consider all qualified applicants without regard to race, color, religion, sex, gender identity or expression, sexual orientation, national origin, age, disability, veteran status, or any other legally protected status.