About the Role:

We’re seeking a highly technical, product-minded individual to lead ongoing development of Olive, an AI-powered chatbot designed for pregnancy centers. You’ll own the evolution of Olive’s logic, flows, and integrations—ensuring it delivers sensitive, compliant, and human-centered interactions across web and SMS.

Responsibilities:

• Own the roadmap and technical direction of Olive, balancing long-term vision with rapid iteration based on test sessions and client feedback.
• Build and maintain a structured scripting system (JSON-based) that drives chatbot behavior and branching logic.
• Manage and refine AI prompt templates to ensure natural, appropriate, and context-aware conversations (5th grade reading level, trauma-informed tone).
• Oversee the SMS communication layer (Twilio-based) and ensure message delivery, session continuity, and mobile-first UX work reliably.
• Implement and manage integrations with external APIs (e.g., Acuity Scheduling, eKYROS, Airtable, etc.) to automate real-world actions triggered by user interactions.
• Maintain and gradually transition infrastructure from a Node.js + PHP (v0) stack to a full Next.js + React architecture (v1).
• Drive admin dashboard enhancements: secure auth (RBAC), editable client templates, session reviews, GPT traceability.
• Manage GPT-driven logic via structured tags (e.g., intent, ultrasound_confirmed, appt_requested) that shape conversation state.
• Troubleshoot session anomalies, token overflows, and edge cases in user-interrupted or paused states.
• Support script localization (e.g., Spanish) while preserving flow logic.

Required Qualifications:

• 3+ years full-stack experience (Node.js, Express, SQL, JavaScript).
• Deep familiarity with SMS-based communication systems (e.g., Twilio Programmable Messaging).
• Proven experience integrating external APIs and syncing real-time or async data across systems.
• Strong product ownership or technical PM background, ideally within conversational AI or chatbot platforms.
• Proficiency in structured content management (JSON, Markdown) and conversational flow design.
• Solid understanding of prompt engineering, current GPT model behavior, and AI conversation design principles.
• Comfortable with Git, production debugging, and working in a lean, evolving product environment.

Bonus:

• Background in healthcare, nonprofit tech, and pro-life organizations.
• Familiarity with eKYROS, WayCool or similar case management tools.
• Understanding of accessibility and trauma-informed UX.

Job Type: Full-time

Pay: $90,000.00 - $120,000.00 per year

Benefits:

• 401(k)
• 401(k) matching
• Dental insurance
• Health insurance
• Life insurance
• Paid time off
• Parental leave
• Retirement plan
• Vision insurance

Work Location: Remote