I am seeking an experienced, tech-forward bookkeeper to optimize and manage my personal and trust bookkeeping with a strong focus on AI integration and automation. Accounts Involved: Personal accounts A trust that includes a brokerage account Five (5) capital accounts for estate beneficiaries Project Goals -Migrate from manual spreadsheets (Excel/Google Sheets) to a modern, intuitive bookkeeping platform. -Implement AI-friendly tools to automate as much of the monthly bookkeeping, reconciliation, and estate management process as possible. -Set up visual dashboards and easy-to-read reports for both personal and trust accounts. -Provide ongoing monthly oversight with a 1x/month virtual meeting for reconciliation, monitoring, and strategic adjustments. Phase 1 – Setup & AI Optimization (One-Time Project) -Review and understand my current Excel/Google Sheets bookkeeping structure. -Recommend the best AI-enabled accounting platform (QuickBooks Online, Zoho Books, Xero, or similar) with automation capabilities for: -Bank & brokerage account syncing -AI-driven transaction categorization -Automated capital account tracking for beneficiaries -Automated report generation -Migrate all existing data into the new system while ensuring historical accuracy. -Integrate relevant AI tools or add-ons (e.g., Dext, AutoEntry, QuickBooks AI features) to reduce manual work. -Create custom visual reports and dashboards for ongoing financial clarity. Phase 2 – Monthly AI-Enhanced Management -Oversee automated data feeds and reconciliations. -Verify and adjust AI categorizations to maintain accuracy. -Maintain trust ledgers, brokerage reconciliations, and capital account balances. -Provide monthly visual financial summaries. -Meet 1x/month to review reports, discuss updates, and refine automation settings as needed. Preferred Freelancer Profile -Minimum 5 years of bookkeeping experience -Direct experience with trust accounting and managing capital -accounts for beneficiaries -Strong knowledge of investment/brokerage account reconciliation -Proficient in AI-powered accounting platforms and automation tools -Skilled at data migration from spreadsheets to modern platforms -Excellent communication skills for monthly virtual reviews -Proactive in recommending process improvements