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:

• 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

• 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.

• 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.

• 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.

• 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.

• Minimum 5 years of experience in software engineering, systems management, or application development, including ownership of production systems.
• Strong technical knowledge of ASP.NET Webforms with VB.NET code-behind (C# /.NET background acceptable), Python, FastAPI, MySQL, Postgres databases, React, MySQL databases, web applications, API integrations, and Google Cloud Platform or equivalent (AWS, Azure).
• Experience leveraging AI coding tools and 2+ years building production LLM applications — RAG pipelines, vector databases, and major LLM APIs. Experience with MCP server design and LLM orchestration frameworks.
• Knowledge of system architecture, cybersecurity best practices, access management, and data governance principles.
• Ability to independently manage technical projects, troubleshoot complex issues, and balance multiple priorities in fast-paced environments.
• Strong communication and collaboration skills, with the ability to explain technical concepts to non-technical stakeholders.
• Experience in nonprofit, education, or public-sector organizations preferred.
• Bilingual English and Chinese (Cantonese or Mandarin) preferred.

Other Requirements:

• Annual Physical exam and TB Clearance
• Criminal Background and Child Abuse Index Clearance
• Adherence to the Confidentiality Agreement and Child Abuse Reporting Mandate
• Adherence to the Kai Ming Code of Conduct and all internal policies and procedures
• Accountable for the health, safety, and supervision of all children, families, and staff interactions
• COVID-19 Vaccination Requirement: Proof of COVID-19 vaccination record

Equal Opportunity: Kai Ming provides equal employment opportunities for staff and candidates regardless of race, color, religion, national origin, gender, sexual orientation, age, marital status, military status or disability in accordance with local, state and federal guidelines. We strongly encourage people from diverse backgrounds to apply. We are committed to creating a diverse and inclusive workforce.