AI Benefits Compliance Monitoring Agent

How Cassidy automates—header using AI

Step 1: Ingest plan data and documents

The Workflow connects to your HRIS, payroll, benefits administration platforms, and carrier feeds to import your complete ERISA plan inventory—including plan documents, prior Form 5500 filings, SPDs, SMMs, and participant census data.

Step 2: Calculate deadlines and generate compliance calendar

Cassidy's AI analyzes each plan's year-end, filing status, and extension elections to calculate Form 5500 due dates, SPD/SMM distribution windows, and SAR timing, then builds a unified compliance calendar with configurable lead times and escalation triggers.

Step 3: Generate and version disclosure documents

The Workflow assembles wrap SPDs, produces SMMs tied to adoption dates, and creates SAR notices using controlled templates—maintaining full version history with redlines and approval tracking for fiduciary records.

Step 4: Execute compliant distribution

Cassidy orchestrates multi-channel delivery based on DOL safe harbor rules, building recipient universes from your participant data, handling email with bounce remediation, coordinating postal mail for those without valid electronic addresses, and logging every delivery event.

Step 5: Manage Form 5500 filing

The Workflow pre-populates Form 5500 schedules from prior-year data and current census, validates against eFAST2 requirements, tracks extensions via Form 5558, and captures filing acknowledgements to trigger downstream SAR production.

Step 6: Centralize audit-ready evidence

Cassidy maintains an immutable evidence vault containing all SPDs, SMMs, distribution proofs, eFAST2 confirmations, committee approvals, and retention attestations—exportable on demand as a complete EBSA audit binder with chain-of-custody metadata.