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Portfolio company · Property management

SimplyStay — PMI Miami Coast

Owner statements that check their own math against QuickBooks.

Chart: owner statement prep reduced from 30–60 minutes to minutes, with automated validation

Property management is won or lost on the monthly owner statement: bookings, fees, expenses, and payouts across multiple ownership entities — where one wrong number costs a client.

An operations platform that syncs the booking system (Guesty) and QuickBooks Online both ways, generates owner statements automatically, and validates every statement against accounting truth before a human sees it — grading each one exact-match, within-a-dollar, or material-variance. A simulation engine dry-runs postings against actual QuickBooks bills before anything commits. It also runs lead follow-up and market intelligence for the management business.

SimplyStay operations platform system diagram
  • 400+ reservations synced with complete financials — revenue, fees, taxes, commissions, payouts
  • Full QuickBooks ledger integration down to the transaction line
  • Every statement self-audited before publishing — review shifts from "check everything" to "check the flagged exceptions"
  • Manual statement prep typically runs 30–60 minutes per property per month; here it's generate, validate, publish

Reservation and ledger counts from the production database; prep-time range is the industry norm for manual statement workflows.

AI that touches money has to prove itself. This system audits its own output against the books — every statement, every month.

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