Fractional CTO

The organization is an early-stage AI / human-development startup built on a behavior-modeling technology that changes how people grow and level up. The team is hiring a fractional CTO to lead a critical execution window. You'll validate and harden the system architecture (founder-proposed), stand up privacy-preserving LLMs and agentic workflows, implement HIPAA-grade security practices for highly sensitive PII (separating identity from observation at the schema level), and deliver the technical story and demonstrable builds needed to attract long-term technical leadership and support near-term commercial launches. Target commitment is roughly 8–12 hours/week (about 30–50 hours/month) over an initial ~3-month engagement.

Responsibilities

• Validate, harden, and document the system architecture for production readiness and investor review.
• Design and implement security and privacy controls for highly sensitive PII — HIPAA-grade practices, with identity separated from observation at the schema level.
• Stand up privacy-preserving LLMs and agentic workflows for production use.
• Build database-driven infrastructure (e.g., Postgres) — including a survey/intake engine and pipelines supporting outcome-style analysis.
• Create interim tooling and protocols to capture outcomes and enable later statistical validation.
• Manage and mentor offshore engineers and contractors to deliver cost-effective builds.
• Translate technical tradeoffs into clear narratives for the CEO, investors, and commercial partners; support positioning and messaging.
• Drive delivery of major technical milestones and initial commercial launches within the engagement window.
• Recruit or recommend follow-on hires (e.g., data scientist/statistician) and help transition toward long-term technical leadership.

Qualifications

• Proven senior engineering / CTO experience (fractional or full-time) at early-stage AI startups.
• Hands-on LLM expertise in production — including privacy-preserving deployment (de-identification before inference, zero-retention or self-hosted models).
• Experience designing agentic / automated workflows and AI-driven product features.
• Deep data-security and privacy expertise for sensitive PII; HIPAA experience strongly preferred.
• Strong backend and database experience — especially Postgres and database-driven application design.
• Experience building pipelines and tooling for outcome measurement, evidence-style analysis, or statistical/outcomes workflows.
• Track record managing offshore engineers and remote contractors to ship production systems.
• Exceptional communicator — can distill complex technical topics for investors, executives, and non-technical stakeholders, and support messaging.
• "Gearhead" mentality: excited about engineering precise primitives, protocols, and rulesets that support large-scale systems.
• Builds precise, scalable systems, takes clear positions, and pushes back constructively.
• Available roughly 8–12 hours/week for an initial ~3-month engagement and able to hit aggressive milestones.