AI Systems & Innovation Manager

Job Title: AI Systems and Innovation Manager

Organization: Kai Ming Head Start is a non-profit 501(c)(3) organization that provides free and high-quality Head Start and preschool services to eligible children ages 0-5 years old in San Francisco, CA with funding from Head Start, the California Department of Education, and the San Francisco Department of Early Childhood.

Job Summary:

Kai Ming Head Start is seeking a hands-on, mission-driven leader to oversee and modernize the organization’s internal technology systems while helping build the next generation of AI-enabled operational tools for the nonprofit and early childhood education sector. This role is responsible for maintaining and evolving Jupiter, Kai Ming’s internal database built on ASP.NET platform supporting operations, reporting, and program management, while leading the development of AI conversational agent, an AI-powered knowledge and workflow platform designed to improve information access, automate workflows, and support smarter decision-making.

The ideal candidate is both highly technical and operationally minded — someone who can stabilize and improve existing systems while strategically planning for scalability, product growth, and future external applications. This role requires a builder mentality, strong AI fluency, and the ability to translate complex technology into practical, user-centered solutions.

Job Type: Full Time, Exempt

Report to: Director of Finance

Essential Duties:

Systems Leadership & Platform Development

• Maintain and oversee Internal Jupiter system operations, uptime, performance optimization, bug triage, deployment coordination, and data integrity.
• Lead gradual modernization of legacy ASP.NET/MySQL architecture using modern engineering practices and AI-assisted development tools.
• Improve system usability, automation, and workflow efficiency for internal users across administrative and program teams including education, family services and workforce development programs.
• Design scalable architecture and technical roadmaps that support future multi-program or external partner adoption.
• Identify opportunities to consolidate fragmented workflows, reduce manual processes, and improve operational visibility through technology.
• Strategize for scalable infrastructure, product development, and prospective third-party integrations

AI Strategy & Intelligent Systems

• Lead development and governance of the AI conversational agent platform, including:
  • retrieval-augmented generation (RAG) systems
  • vector databases and embeddings
  • MCP integrations
  • citation-based AI responses
  • internal AI search and workflow automation
• Evaluate and implement practical AI solutions that improve staff productivity, reporting, knowledge management, onboarding, and operational decision-making.
• Develop AI governance standards, prompt management practices, access controls, and responsible-use guidelines.
• Research and pilot emerging AI tools and frameworks relevant to nonprofit and education program operations.

Engineering & Technical Operations

• Utilize AI coding tools such as Cursor, Claude Code, GitHub Copilot, and related platforms to accelerate development, debugging, refactoring, and documentation.
• Oversee code quality, version control, CI/CD pipeline standards, testing procedures, and technical documentation.
• Establish sustainable development workflows and engineering practices suitable for a small but growing technology team.
• Support API integrations, automation pipelines, reporting systems, and interoperability between platforms.

Security, Compliance & Risk Management, oversee the area in collaboration with an external contractors

• Establish and maintain security protocols including:
  • Access reviews
  • Secrets management
  • Audit logging and incident response planning
  • Patch management, backup and recovery procedures
• Manage external technology, hosting, and security vendors including vulnerability assessments and penetration testing.
• Develop disaster recovery and business continuity procedures.

Cross-Functional Leadership

• Collaborate closely with leadership and operational teams to translate organizational needs into technical solutions and follow through on implementation.
• Supervisor and coordinate the work of software engineers, UI/UX designers, IT support staff and any other staff or contractors that are involved in the work.
• Communicate technical concepts clearly to non-technical stakeholders.
• Prepare reports, dashboards, presentations, and strategic recommendations for executive leadership and the Board of Directors.