EVERY GUEST · ONE PROFILE · ONE STORY
"Every customer is a story. We make sure none of them are lost."
Four data points so this proposal doesn't read as theoretical. We've done the engineering before; the hospitality vertical is the new edge.
We've been shipping these integrations for enterprise retail clients since Lightspeed's earlier versions. The data model is familiar territory.
The hospitality vertical is new for us. The plumbing isn't. We've worked directly with Lightspeed's internal team on prior builds.
A live client running similar segmentation logic: parent SKU rollups, varietal grouping, Klaviyo event architecture. Happy to introduce you.
usualsuspects.wine →Custom Shopify events platform managing 1,000+ clubs. Same data discipline, different shape.
Dear Maddy, Monica and Michelle. The proposal you're reading is built around what you told us.
Thank you for the detail in your reply, Maddy. It changed how we want to shape this work.
The most important sentence in your reply was this: NowBookIt is operationally connected to Lightspeed, but you don't yet know exactly what data is passing through, or whether it's useful from a Klaviyo perspective. That single unknown changes the scope of this build by a meaningful margin. Anyone quoting a full fixed price without confirming what's already flowing between those two systems is guessing.
So we've structured this differently. One week of paid discovery comes first. We audit what's there, map your data wishlist against reality, and only then do we lock the build, the timeline and the final price. If discovery turns up something we didn't expect, we'll talk it through and re-quote that piece before either of us commits to it.
Everything else in your reply gave us a clearer picture than we had before. We know one visit should equal one post-visit flow with transactions preserved underneath. We know your product metadata layer is the system that makes the whole thing useful, and we know exactly what fields that layer needs to carry. We know the four flows you've already built (Welcome, Abandoned Checkout, Win-back and Birthday) need to stay and get enriched, not be rebuilt. We know the phasing is Dunsborough first, Cowaramup at the August soft launch, Small Wonder in September.
The rest of this document walks through how we'd do it.
Pulled directly from your reply, Maddy. If any of these are wrong, tell us before we lock scope in Phase 0.
Klaviyo as source of truth across all three brands. Wayfinder Dunsborough and Cowaramup share one Klaviyo with venue tags. Small Wonder runs in its own Klaviyo environment, isolated.
A single sitting can produce multiple Lightspeed transactions. They roll up into one visit with one post-visit trigger, line items preserved underneath.
SKUs like WFCH25, WFCH25-GLASS and WFCH25-TASTING all need to mark a guest as a Chardonnay buyer. Brand, varietal, subbrand, vintage, format and SKU translation make that possible.
| Raw SKU | Marketing attributes |
|---|---|
| WFCH25 | Brand: Wayfinder · Varietal: Chardonnay · Vintage: 2025 · Format: Bottle |
| WFCH25-GLASS | Same · Format: Glass |
| WFCH25-TASTING | Same · Format: Tasting |
Around nine lifecycle flows per venue, rolled out in step with the venue calendar. The four flows you've already built (Welcome, Abandoned Checkout, Win-back, Birthday) stay live and get enriched with POS data rather than rebuilt.
Dunsborough first as the proving ground. Cowaramup at the August soft launch. Small Wonder at the September opening. One architecture, three venues, three timelines.
Lightspeed is the operational system of record for the POS data and (we believe) the booking data NowBookIt is already pushing through. Our middleware sits between Lightspeed and Klaviyo, doing three jobs: pulling the right fields, mapping SKUs into useful marketing attributes, and constructing visit-level events so a guest who has two transactions in one sitting only triggers one post-visit flow.
Klaviyo receives clean, enriched profiles and events and runs the lifecycle marketing on top. The Wayfinder venues share a Klaviyo with venue tags on every profile and event. Small Wonder sits in its own Klaviyo, isolated, with the same architecture replicated.
A single sitting can fire two or three transactions through the POS. The integration rolls them up into one visit event so the post-visit flow triggers once, with line items preserved underneath for segmentation and revenue reporting.
Phase 0 audits what's actually there, locks the scope, and fixes the price for the build. Phases 1, 2 and 3 follow the venue calendar. Each phase is a complete, working slice.
Before we build anything, we audit what's actually there. At the end of the week you get a written scope, a fixed price for the build, and the freedom to walk if it's not the right fit.
Foundation. The full architecture stood up on the venue you're already running. All Phase 0 findings translated into a working system before Cowaramup launches.
Same architecture, second venue tag. Cross-venue intelligence becomes possible the moment the doors open.
Parallel build in the separate Small Wonder Klaviyo environment. Isolated data, same engineering applied independently.
Most integrations stop at the plumbing. We don't. Every Wayfinder build ships with a custom dashboard tuned to the metrics that actually connect lifecycle marketing to revenue. Not vanity opens and clicks. The numbers Monica and Michelle want to see on a Monday morning.
In Phase 0 we pick five to eight metrics with you. We build them as a single, fast-loading page you can pull up on a phone in the venue. No Klaviyo deep-link spelunking. No spreadsheet exports.
Included in Phase 1. Not an add-on.
We've built Phase 0 specifically so neither of us is guessing when we commit to the build. But projects move, and new requirements come up. Here's how we handle that.
For anything material that surfaces during discovery (for example, NowBookIt is only passing transactional data and we genuinely need to build a separate booking sync, or the Shopify SKU mapping is more involved than today's example suggests), we'll flag it, talk it through, and re-quote that piece before either of us commits to it. We'd rather have that conversation once with full information than discover it mid-build.
For anything that comes up after scope is locked (new flows, new venues beyond the three, new integrations, new ideas) we'll handle it as a small change request rather than a contract event. Quick conversation, quick price, get on with it. We'd rather keep momentum than treat every adjustment like a renegotiation.
You're our first hospitality client. That earns you a discount the next ten won't get. Phase 0 is fixed. Phases 1, 2 and 3 are launch-partner rates confirmed at the end of discovery. If anything material shifts in Phase 0 we re-quote that piece before either of us commits.
Fixed fee. Non-refundable, but credits in full against Phase 1 if you proceed.
Foundation build. 50% on kickoff, 50% on go-live. Less the Phase 0 credit if you proceed.
Second-venue replication. 50% on kickoff, 50% on go-live.
Parallel Tasmania build. 50% on kickoff, 50% on go-live.
Begins thirty days after Phase 1 go-live. Monitoring, sync health, adjustments, and small change requests across every venue.
The phone numbers are already coming through, so this is configuration rather than engineering. Activating SMS unlocks booking reminders, last-minute table releases and vintage drop alerts. Open rates north of 90%. Hospitality's most underused channel.
As our launch hospitality customer, in exchange for launch-partner pricing we'd like four things that don't cost you money but help us build the next chapter of this product.
Permission to write the story of what we built and what it changed, with numbers, once Phase 1 is live and producing results.
A short piece on camera, ninety days post-launch. Honest, your words, no script.
To two similar hospitality groups in your network. Wineries, restaurants, multi-venue operators.
Wayfinder, Small Wonder and Overstory on our website as launch hospitality partner. We'll show you the placement before it goes live.
The six we expect to come up first. If yours isn't here, reply and we'll add it.
The integration is structured so booking data can come from either NowBookIt (via Lightspeed) or from a future replacement (OpenTable, SevenRooms, etc.) without rebuilding the Klaviyo side. Switching booking platforms means rebuilding one connector, not the whole system.
Low. The O-Series API is well documented and we've already mapped the data model. Phase 0 confirms specific field availability before any build commitment, which is exactly why Phase 0 exists.
Monitoring sync health, fixing breakages, small change requests (new flows, field additions, segment tweaks), Klaviyo configuration adjustments, and ongoing advice. It does not cover net-new venue rollouts (those are scoped separately) or major new integrations.
Yes. The architecture is built for it. Each new venue is a fixed-fee add-on that replicates the Phase 2 pattern. Pricing locked at launch-partner rates for the life of the account.
Six short steps from this proposal to a locked scope and a working Phase 1 build.
Honest reactions welcome. If anything's off, better to surface it now than after a SOW is on the table.
Same pricing as this proposal, with payment terms, deliverables and the change-request mechanism written up cleanly. Phase 1, 2 and 3 numbers confirm at the end of Phase 0.
Together or separately, whatever works for your decision cycle.
We walk through the architecture, the finance flow, and any questions before signature.
One week of discovery. We audit what's there, map your wishlist against reality, and walk you through real data.
You decide whether to proceed into Phase 1 with full information on the table. If you do, the Phase 0 fee credits in full.
Two people. Tim and Ying. We've been building Shopify, Lightspeed and Klaviyo systems for enterprise clients for years. We started Elephant because every client we worked with kept hitting the same wall: their tools didn't talk.
We don't sell software. We sell a layer between your tools. We don't lock you in. We don't bloat invoices with strategy decks. We build the thing, we support the thing, you grow.
Elephants have long memories. They never forget. Same goes for your customer data.
Reply to this proposal and we'll send the SOW with locked pricing. Phase 0 begins the week you sign.