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. The Role As Head of Engineering, you will own the technology strategy and execution for a platform that handles sensitive mental health data at scale. You’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. You 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 checkboxes 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 Your Experience 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 verbal communication skills, comfortable presenting to executive buyers, clinicians, and security teams, and representing engineering as the technical face of the company Security & Compliance Deep, hands-on experience operating HIPAA-compliant systems handling PHI at scale Led or co-led regular pentesting and SOC 2 (Type II) audits end-to-end Familiarity with FedRAMP (Moderate or High) requirements and/or experience preparing an organization for FedRAMP authorization Experience designing and operating authenticated user-facing experiences in healthcare Fluent in modern authentication and authorization Proven experience implementing security controls: encryption at rest and in transit, key management, least-privilege IAM, audit logging, MFA, secrets management, vulnerability management, and incident response Experience owning disaster recovery and business continuity, including RPO/RTO planning, backup and restore testing, and multi-region failover for healthcare workloads Experience with threat modeling, penetration testing programs, Business Associate Agreements (BAAs), and vendor risk management Comfortable owning the security and compliance relationship with enterprise and health plan customers through procurement and audit cycles AI/ML & Data Science Strong technical understanding of modern ML and NLP, including LLMs, RAG, agentic workflows, fine-tuning, evaluations, and guardrails Experience partnering with ML/AI teams to take models from prototype to production, including training pipelines, model registries, inference, monitoring, drift detection, and safety evaluations Working knowledge of MLOps tooling, with hands-on familiarity running ML workloads on Kubernetes and using MLFlow for experiment tracking and model lifecycle management Comfortable reasoning about AI safety, clinical accuracy, hallucination mitigation, and responsible AI in a behavioral health context Experience enabling data science and analytics teams with a modern data stack (BigQuery, Looker, and product analytics) Platform & Infrastructure Proven experience managing cloud infrastructure (AWS, GCP) at scale, including system architecture, cost observability, workload rightsizing, and budget guardrails across engineering teams Strong fundamentals in distributed systems, real-time messaging, API design, data modeling, websockets Strong understanding of Kubernetes, Terraform/IaC, CI/CD, and observability (metrics, logs, traces, on-call) Fluency in Python and modern backend stacks Education Bachelor’s degree in Computer Science or a related technical field required; Master’s or advanced degree preferred Bonus Points Experience integrating with federal or state agencies (e.g., Medicaid, Medicare, VA) Published work, open source contributions, or patents in AI/ML, security, or health tech Compensation & Benefits Fully remote, location-agnostic within US time zones Target base salary range: $205K-$225K Meaningful equity in a VC-backed, revenue-generating, self-sustaining startup Comprehensive health benefits including vision and dental 401k with vested match for full-time, US-based employees Generous PTO and company-wide breaks In-person team gatherings focused on collaboration and team building Interview Process [30 min] Initial screen with Director of Operations [45 min] Security, compliance & healthcare depth interview [45 min] AI/ML strategy & partnership interview [60 min] Technical leadership & systems design interview [45 min] Values and cultural fit interview with cross-functional partners [60 min] In-person people leadership interview with company Founder/CEO Reference checks, background check, and offer How To Apply To beat the bots, we’re going old school for applications. Email us your resume and a non-AI-generated note about why Supportiv is a fit for you to View email address on click.appcast.io. #J-18808-Ljbffr