The operating systemfor trust and estate administration
An estate plan takes months to build and thirty years to execute. Headlight handles the thirty years.
Why Headlight
The documents are signed. The planning is implemented. Everyone assumes the work is done.
It isn't. The documents are only the beginning. GRATs require annuity payments on schedule. Gifts and other transfers may require valuations, tax filings, elections, or other documentation. Trusts need to be funded and administered according to their terms, with ongoing tax, accounting, and reporting requirements that vary by structure. These obligations can continue for years, and too often they're tracked across spreadsheets, calendars, email, and institutional memory.
Headlight reads the planning documents, identifies provisions that may create ongoing administrative obligations, and organizes them into a structured workflow. Your team reviews and confirms what should be tracked. Headlight then monitors the resulting tasks, deadlines, and documentation, and maintains a record of what was completed.
From signed documents to ongoing administration. Nothing important left to memory.
Document intelligence
Review AI output before it hits your records
Upload estate planning documents, tax filings, and entity records. Headlight extracts structured data your team can verify before it becomes part of the household.
Relationship structure
Trusts, entities, and family ties in one view
Map trusts, entities, and people on interactive charts. Filter nodes, adjust card display, and share a read-only link that matches what you configured.
Gift & transfer tracking
Track every gift, loan, and transfer in one place
Record gifts, GRATs, leases, loans, and charitable contributions. Headlight tracks exemption usage per donor, flags transfers that may create gift-tax reporting requirements, and proposes filing tasks your team confirms.
Tasks and deadlines
See what's overdue, at risk, and coming due
Filing deadlines, GRAT annuities, lease expirations, and note payments are proposed from your records for your team to confirm. Filter by assignee, household, or status across list, calendar, and timeline views so overdue work stands out firm-wide.
Relationship report
Turn activity into a client-ready recap
Pull meetings, milestones, and completed tasks into one report. Filter by trust or entity, choose what to include, and generate a draft summary your team can review before sharing.
Question answering
Ask questions. Get answers with citations.
Ask Headlight in plain language. Each answer links to the page and passage in your firm's documents, so your team can verify before acting.
Security
How Headlight protects your firm's data
Built for advisory firms, family offices, trust companies, and wealth management firms that handle sensitive client information.
Your firm is isolated from other customers
Each customer organization is logically isolated. PostgreSQL row-level security enforces tenant boundaries at the database layer. The application applies tenant-scoped access controls on every query.
Extra encryption for the most sensitive fields
Contact details, extracted document text, and sensitive financial fields receive additional application-layer field encryption (AES-256-GCM) with centrally managed keys.
We do not use your data to train AI
Headlight does not use customer content to train or fine-tune AI models. Inference runs on your documents to classify and extract data, summarize records, and answer questions from your firm's files.
Early access
Request early access for your firm
Headlight is in a closed beta. Tell us about your firm and we will follow up with next steps. Published pricing is for invited firms.