Sailsquare — 5 years on the platform, alongside their team.
- Solution
- Build
- Industry
- Marketplace
- Effort
- 1.5 FTEon average
- Together for
- 5 yearssince 2021
- Status
- Active
01 · The client
Sailsquare is a marketplace for boating experiences: people who organize trips meet people who book them. Strong seasonality, and an in-house CTO who leads the product.
- Website
- sailsquare.com
- Headquarters
- Milano
- Founded
- 2012
- People
- 10-20
02 · The trigger
The platform had grown with the market, and the original architecture no longer matched what was needed.
It had to be renewed without stopping the service or losing data, while automating internal processes and preparing the system to handle more users, more trips and more bookings.
03 · The technical problem
A marketplace with money flowing between different users, commissions to calculate, and load that concentrates in the booking months. On top of that, an inherited system that had to be understood before it could even be touched — while it kept taking payments the whole time.
04 · What we did
We worked alongside the CTO to renew the web applications and the architecture, automated internal processes by integrating CRM, bookings and reporting, and built release pipelines and infrastructure that scales with demand. In the first stretch the CTO reviewed every change: trust came from the work, we did not ask for it upfront.
05 · The partnership
- 2021
Working alongside the CTO
Every change goes through the CTO's review.
- 2022
New architecture
Web applications rebuilt without stopping the service.
- 2023
Automated processes
CRM, bookings and reporting connected.
- 2024
Elastic infrastructure
Release pipelines and infrastructure that follows the season.
- Today
Ongoing partnership
Before

After

06 · Where things stand now
5 years in, and the collaboration continues. The CTO focuses on the product, and we help him move it forward. It's also the relationship other clients have come from.
07 · The voice
È un fortuna poter lavorare con persone intelligenti e appassionate: sviluppatori che amano vedere le cose funzionare bene e che si approcciano a ogni nuova tecnologia con curiosità genuina e capacità di apprendimento.
Lane: Build · Vertical: Marketplace
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