Chief Engineering & Security Leader, Healthcare AI

What’s Supportiv?

Supportiv is a peer-to-peer mental/emotional wellbeing and resource navigation platform that provides real-time support for everyday life struggles, 24/7/365, at 1/6 the cost of therapy, ensuring true accessibility.

Our multi-patented process matches users in seconds to dynamically-formed, real-time moderated small peer group live chats (max. 5 users) based on their natural-language-expressed needs. As conversations unfold, we intelligently refine our understanding of users’ needs and, in real time, precisely match users with the most relevant and helpful resources and services using retrieval systems and adaptive agentic flows.

Supportiv empowers users to cope, problem-solve, and heal in a highly user-friendly and practical way by harnessing advanced AI and NLP techniques, while preserving genuine human connection.

We serve top employers and health plans, including two Fortune 10 companies. 92% of users rate their experience 4 or 5/5 stars, and we deliver clinical-grade outcomes unmatched in the industry.

As Head of Engineering, you will own the technology strategy and execution for a platform that handles sensitive mental health data ’ll lead a team of 8+ engineers across our core platform, AI/ML systems, and infrastructure, setting the bar for security, compliance, reliability, and responsible AI in healthcare. You’ll partner closely with our Founder, Clinical, Security, and Customer Success teams to scale Supportiv into its next chapter of larger enterprise and health plan deployments, direct to consumer marketplaces, and more sophisticated LLM-driven experiences.

This role is highly customer-facing. You will represent Supportiv’s engineering and security posture directly to enterprise customers, health plans, and partners, leading technical reviews, security and compliance conversations, and architectural discussions throughout the sales and renewal cycles.

This is a rare opportunity to shape the engineering culture and architecture of a company sitting at the intersection of healthcare, mental health, and applied AI, where every line of code directly impacts whether someone gets the emotional support they need.

• Hands-on engineering leader with deep technical credibility and a builder’s mindset
• Passionate about healthcare and the responsible use of AI to improve human lives
• Operate with a security-first mindset and treat HIPAA, SOC 2, and FedRAMP not as check boxes but as core engineering disciplines
• Able to translate fuzzy business and clinical requirements into crisp engineering roadmaps and product specs
• Exceptional communicator, comfortable in the room with Fortune 10 customers, health plan security teams, clinicians, and engineers
• Strong recruiter, mentor, and coach who elevates everyone around you
• Bias toward action and comfortable making high-stakes calls with incomplete information
• Excited to roll up your sleeves on architecture, code review, and incident response, not just slides and status reports

Leadership & Scale

• 10+ years of software engineering experience, with 5+ years in engineering leadership roles
• 5+ years leading engineering at a digital health, behavioral health, mental health, or other healthcare technology company (required)
• Hands-on experience selling into or integrating with health plans and Fortune 500 employers, including leading technical reviews, responding to security questionnaires, and supporting enterprise procurement and renewal cycles
• Experience managing multinational engineering teams of 8 to 15, including managing managers and tech leads distributed across US, EU, and Global
• Strong track record of partnering with Product to author detailed product specs, technical design docs, and PRDs, translating clinical and business requirements into clear, actionable engineering work
• Analytical, experiment-driven approach to product and engineering development: defines clear success criteria up front, establishes meaningful KPIs, instruments, and monitors them continuously, and tracks ROI across initiatives
• Track record of hiring, developing, and retaining high-performing engineers in a remote-first environment
• Exceptional written and…