Most venues lose 30–60% of first-time guests permanently. Osbert finds them before they're gone — and tells the team exactly what to say.
The Osbert opportunity engineThe data
What Osbert knows about each customer
Right now, Osbert pulls data from the venue's Square POS system — the same system they already use to take payments. No new hardware, no manual data entry. Every time a customer visits and pays, Square records it. Osbert reads that history every night.
From Square, Osbert builds a profile for every customer: how many times they've visited, how much they've spent in total, and when they last came in. That's enough to spot every meaningful pattern below.
The five signals
What Osbert is watching for
Each night the engine checks every customer against five patterns. When a pattern matches, Osbert creates an opportunity — a card in the dashboard that tells the team who to reach out to and gives them an AI-drafted message to send.
A customer left a negative review or a staff member marked their feedback as needing care. This is always the highest priority in the queue — a bad experience that goes unacknowledged becomes a lost customer and a bad review.
A customer who spends significantly more than the average guest hasn't been in for over a month. These are the customers who drive disproportionate revenue — losing one quietly is a big deal.
A customer who has visited three or more times — so they clearly liked it — but hasn't been back for more than two months. These are the highest-conversion outreach targets: they already know the venue, they just need a prompt.
A customer who has visited at least twice hasn't been in for over six weeks. Not yet a lapsed regular, but showing a pattern worth a gentle nudge before the habit breaks entirely.
A first-time guest hasn't come back after 1 to 8 weeks. The first-to-second-visit conversion is one of the highest-value moments in any venue's customer lifecycle — most of the guests who become regulars return within 60 days of their first visit, or not at all.
The workflow
What happens after Osbert spots an opportunity
Spotting the right customer is only half the job. Osbert then guides the team through turning that signal into a real conversation — without them having to write a single word from scratch.
Every morning the manager opens Osbert and sees a prioritised list — unhappy customers first, high-value regulars next, then everyone else.
One click generates a personalised draft based on the customer's history, the opportunity type, and the venue's voice. The manager sees the draft instantly — no prompting required.
The manager edits if needed and approves. The whole process takes under a minute per customer. The system records who approved what and when.
The outreach goes out via the venue's preferred channel. The opportunity is marked sent — it won't appear again unless new signals emerge.
When the customer comes back, Osbert records it. The dashboard shows which outreach led to which return visits and exactly how much revenue was recovered. This is how we prove ROI.
The numbers
How Osbert estimates the revenue at stake
Every opportunity in the queue shows an estimated value — the revenue Osbert thinks is recoverable if that customer comes back. It's calculated from the customer's own history: their average spend per visit, multiplied by how likely they are to return multiple times if re-engaged.
Why the queue is ranked
Not all opportunities are equal
A venue team can only send so many messages in a morning. Osbert ranks every opportunity so the most important ones are always at the top — the manager never has to decide where to start.
The ranking takes three things into account:
The priority score is recalculated every single night. A customer who was fifth on Monday is automatically first on Friday if they've been silent for another week. No manual sorting needed — the queue always reflects reality.
Quality control
The queue stays clean automatically
One of the things that makes venue teams lose faith in CRM tools is stale data — a customer who came back last week still showing as a "lapsed regular." Osbert solves this without any manual work.
Every night, alongside creating new opportunities, the engine also closes any opportunity whose conditions no longer apply. If a customer who was flagged as "first visit — no return" walks back in on Wednesday, by Thursday morning that card is gone from the queue. Automatically. The team is never chasing someone who already came back.
Common questions
What sales teams ask
They connect their Square account — that's it. Osbert does the rest. The first night after connection, the engine runs and the queue is populated with real opportunities from real customer data.
Square is the current integration. SevenRooms is next. The architecture is built for multiple connectors — each one adds a new stream of customer data that the engine can use. This is a roadmap conversation, not a blocker.
Through Osbert's dashboard. The approved message is ready to send via the venue's preferred channel. The outreach is personal — it looks like it came from the manager directly, not from a marketing tool.
Yes. Every return visit after an outreach is attributed. The dashboard shows total recovered revenue, by week and by month, with a breakdown by opportunity type. This is the core ROI story.
It means the engine can run twice accidentally and nothing breaks — no duplicate cards, no double messages. It's a reliability guarantee. For sales purposes: Osbert is production-grade, not a prototype.
The full developer doc covers every threshold, formula, and architecture decision — with diagrams.