--- title: Bookly/Square Integration Status & Strategy Reset — 2026-04-05 type: article created: '2026-04-05' updated: '2026-04-05' source_docs: - raw/2025-10-28-la-marie-beauty-project-call-97373418.md tags: - client/la-marie-beauty - project/lmb-website - bookly - square - woocommerce - zapier - integration - technical-blocker - leadership-transition - booking-flow layer: 2 client_source: LaMarie Beauty industry_context: ecommerce transferable: false --- ## Overview Status review of the Bookly/Square integration for the [[wiki/clients/current/lamarie/_index|La Marie Beauty]] website project. The meeting surfaced a fundamental technical blocker in the Bookly-to-Square payment flow, prompted a pivot toward routing bookings through WooCommerce, and introduced Kimberly Gehrmann as the incoming technical lead replacing Katie Schueller (maternity leave). **Attendees:** - **Asymmetric:** Chris Ostergaard, Melissa Cusumano, Mark Hope - **La Marie Beauty:** Roxana Lopez, Katie Schueller, Lisa Frommelt - **Incoming technical lead:** Kimberly Gehrmann (gehrmann.kimberly@gmail.com) --- ## Key Decisions 1. **Bookly/Square integration is blocked and may not be viable.** The core issue — Square requiring a "card on file" checkpoint that Bookly cannot satisfy — is a fundamental mismatch, not a configuration problem. The team agreed this is not necessarily a kill decision yet, but the clock is running. 2. **WooCommerce routing will be investigated as the primary alternative.** Rather than passing payment through Square directly, routing the Bookly booking flow through WooCommerce may provide the flexibility needed for card capture and a unified cart. 3. **Non-negotiable requirements were re-anchored.** Two requirements were explicitly restated as non-negotiable: - A **single checkout cart** combining products and services in one transaction. - The **entire booking experience must remain on the La Marie Beauty website** (no redirects, no new tabs). 4. **Sunk cost framing acknowledged.** Kimberly explicitly named the sunk cost fallacy risk. The team agreed to pursue open feasibility questions before making a final call on Bookly, but committed to not letting prior investment override the core requirements. 5. **Kimberly's role defined.** Asymmetric retains hands-on development responsibility. Kimberly provides architectural guidance, technical oversight, and will help evaluate feasibility and debug complexity. She is engaged for the full website project scope, not just the Bookly phase. --- ## Technical Blocker Detail ### Bookly ↔ Square Payment Incompatibility Square requires a **"card on file"** checkpoint to finalize any booking. Bookly's Square integration offers only two options: | Option | Status | |---|---| | Full prepayment for the service | ❌ Not acceptable for La Marie Beauty's model | | No payment / no card captured | ❌ Not acceptable | There is no native path in Bookly to capture card details without charging the full amount. This blocks the integration entirely under the current setup. ### Zapier Workflow Inconsistencies Even setting aside the payment issue, the Zapier automation layer has reliability problems: - **Service ID mismatch:** Zapier successfully finds Square IDs for some services (e.g., "No Fluff Dermaplane," "Injective Consultation") but returns no results for others (e.g., "B12 Injections," "Neurotoxin/Botox"). Services not marked as bookable online in Square are invisible to the Zap. - **Incorrect IDs returned:** For services it does find, Zapier sometimes returns an ID that doesn't match what Square actually accepts, causing the booking creation step to fail. - **Calendar/availability sync unverified:** Bookly staff schedules have not been confirmed to sync correctly with Square availability, meaning test bookings may be failing simply because the slot appears unavailable — not because of the integration logic. ### UX Issues The Square checkout popup that surfaces at the end of the Bookly flow is visually jarring, not brand-aligned, and largely uncustomizable (it is served by Square, not Bookly). Chris noted the overall UX would likely have a negative impact on conversion. --- ## Proposed Path Forward: WooCommerce Routing Chris proposed reactivating the WooCommerce feature within Bookly so that booking payments route through WooCommerce rather than directly through Square. The rationale: - WooCommerce already handles product orders on the site and syncs with Square for inventory/payment. - Routing bookings through WooCommerce could enable a **single cart** for both products and services. - WooCommerce may offer more flexibility for card capture without requiring full prepayment. **Known constraint:** Bookly does not natively support product variations. The team has been working around this by building individual variant pages (e.g., the Vampire Facial sample page) where each variant routes to a specific Bookly service. This workaround needs to be validated against the WooCommerce routing approach. Chris will consult with an internal developer (Ishak) on whether custom code can bridge remaining gaps, particularly around card detail capture. --- ## Leadership Transition **Katie Schueller** is transitioning off the project ahead of maternity leave (due date: November 8). **Kimberly Gehrmann** joins as technical lead: - Background: full-stack software engineer, fractional CTO, founder - Familiarity with Square APIs (has been reviewing them in parallel work with Lisa) - Former La Marie Beauty client — brings consumer-side context on the aesthetics industry - WordPress experience is primarily custom-coded deployments rather than plugin-based, so she is onboarding to the Bookly/WooCommerce/Zapier stack - Will review all recorded Fathom sessions and historical notes to get up to speed Melissa is compiling a consolidated onboarding document for Kimberly that includes: project asset links, Miro board, shared drive, Fathom recordings back to the Bookly kickoff, and historical meeting notes. --- ## Action Items | Owner | Action | Due | |---|---|---| | **Chris (Asymmetric)** | Investigate WooCommerce routing as solution for single cart + card capture | Thursday | | **Chris (Asymmetric)** | Consult internal developer on custom code options for card-on-file capture | Thursday | | **Chris (Asymmetric)** | Internal meeting with Ishak to assess Bookly UI customization limits | Before Thursday | | **Melissa (Asymmetric)** | Share consolidated project assets document with Kimberly | ASAP | | **Melissa (Asymmetric)** | Compile and share historical meeting notes with Kimberly (back to ~project start) | ASAP | | **Kimberly (LMB)** | Send follow-up email summarizing technical investigation points for next meeting | EOD same day | | **Roxana (LMB)** | Send Vampire Facial variant page screenshots/notes to Melissa | Same day | | **Roxana (LMB)** | Schedule follow-up meeting with Melissa (+ Kimberly) to review service variation page feedback | This week | --- ## Transcript Excerpts **On the core payment blocker:** > "With Bookly, the only checkpoint that you have is either you pay for the service or you don't, basically. You're not given the option, even with the Square integration, to just input your card details." — Chris Ostergaard **On the non-negotiable requirements:** > "One thing very critical to Lisa… was that when they are checking out, they can check out with one cart, their appointment, and any products that they had wanted… And from the demo, Bookly was able to accomplish that, which was a key reason that we went forward with this." — Katie Schueller > "The entire booking experience must remain on the La Marie Beauty website. It doesn't navigate away from our website like Square currently does and opens a new tab." — Katie Schueller **On sunk cost risk:** > "At what point is this now we've entered into sunk cost fallacy land, where we're continuing to hope that it's going to do what is critical at the end of the day — which is that single cart for product and services, the subscriptions, and then keeping the checkout experience within the website?" — Kimberly Gehrmann **On Kimberly's role:** > "My understanding is that Asymmetric would be doing, at the end of the day, a lot of the hands-on keyboard, but I'm certainly available to lend thought when it comes to architecture and systems." — Kimberly Gehrmann --- ## Related - [[wiki/clients/current/lamarie/_index|La Marie Beauty — Client Index]] - [[wiki/clients/current/lamarie/lmb-website|LMB Website Project]]