Christian Ritter built Sidekick to give Square sellers true real time awareness.
After a decade as both a Square partner and a Square powered cafe owner, Christian experienced the same problem over and over. The dashboard buried simple, critical insights. Sidekick fixes that with hyper granular alerts and AI summaries operators can trust.
Christian has been a Square user for more than ten years. He first supported enterprise merchants as a telecom sales engineer where Square was one of his accounts. Later he opened a cafe in San Francisco, running point of sale, payroll, and team management entirely on Square.
On April first he started building Sidekick from scratch, grinding through nights and weekends. The initial concept was a conversational AI that could answer questions like how many lattes sold with oat milk last month. During testing the real breakthrough surfaced: laser focused push alerts that arrive the moment something meaningful happens.
Today Sidekick routes sales, refunds, discounts, online orders, and team milestones across multi location accounts. That means owners stay connected without living inside dashboards.
Christian Ritter, Founder
What makes Sidekick different
- Hyper granular alerts do not exist anywhere else in the Square ecosystem.
- Sidekick is built and battle tested by an operator who still runs on Square every day.
- Every cohort gets white glove onboarding, tuned alert rules, and direct feedback loops with Christian.
The values that keep Sidekick focused on real operator impact
Tools and workflows that power Sidekick
From Square admirer to Sidekick founder
Sidekick is in alpha with Square sellers giving real world feedback
Christian continues to build in public, sharing progress on Reddit, X, and inside the founding cohort. Every alert rule and insight is sharpened alongside operators who want to stay obsessed with their business.