Senior AI / Full Stack Engineer for Executive AI Chief of Staff

I am an executive and investor managing several companies, and I am looking for an experienced engineer to take over an existing AI Chief of Staff project and turn it into a reliable system I can use daily. The project already has a codebase, architecture documentation and tests. Significant time has gone into development, but it has not yet become a usable product. I need someone who can assess the existing work, identify what is worth retaining, resolve implementation and deployment issues, and take ownership of delivery. The goal is an AI assistant that understands my responsibilities across multiple businesses and helps me manage communications, priorities, meetings, commitments and follow-ups. The intended capabilities include: • Connecting securely to email, calendar and relevant documents. • Producing daily briefings with important messages, upcoming meetings, decisions and outstanding commitments. • Identifying unanswered emails, overdue follow-ups and tasks that need attention. • Preparing email drafts and meeting briefs using relevant correspondence and documents. • Maintaining useful, accurate memory of people, projects, decisions and commitments. • Keeping information and permissions appropriately separated across companies. • Providing references to the underlying emails or documents so I can verify its conclusions. • Supporting proactive assistance, with clear approval requirements for sending messages or taking other external actions. One important requirement is that I use a central email account for work across multiple companies. The system must identify the appropriate company and project context within that account. It cannot assume that each mailbox represents a single organization. The immediate priority is a working pilot. I want to be able to sign in, connect an authorized email and calendar account, receive a useful briefing based on real information, identify outstanding follow-ups and generate drafts for review. The initial pilot can focus on reading information and preparing drafts, with broader capabilities introduced after that workflow is reliable. Your responsibilities will include: • Reviewing the existing repository, architecture and implementation. • Recommending a practical path to a usable pilot, including what to retain, simplify or replace. • Resolving authentication, integration, application and deployment blockers. • Implementing and testing the core workflows against clear acceptance criteria. • Handling credentials, access permissions and sensitive business information securely. • Providing deployment documentation, monitoring and a maintainable handover. • Demonstrating progress through working software at agreed milestones. I prefer using proven services for standard infrastructure such as authentication, integrations and hosting. Custom development should focus on the workflows, organizational context, memory and controls that make the assistant useful. You should have strong experience building and deploying applications using LLM APIs, integrating email and calendar services through OAuth, and delivering reliable backend and frontend functionality. Experience with Python, FastAPI, retrieval systems, persistent memory, background processing and production authentication would be particularly relevant. Please include the following in your proposal: 1. One or two relevant AI applications you have personally built and deployed, including your specific contribution. 2. Your experience taking over an existing codebase and bringing it into production. 3. Your proposed approach to the first working pilot and what you would need to inspect before estimating delivery. 4. Your availability, hourly rate or proposed milestone structure, and whether you will personally perform the work. 5. The main technical risks you would investigate first. Detailed project materials and repository access can be provided to shortlisted candidates. There is potential for ongoing work after the initial pilot, but the immediate objective is a dependable system I can start using.