Calendly: 50% Per-Seat Increase — $8 → $12

In January 2026, Calendly raised prices across all paid plans and gutted the free tier. Standard went from $8 to $12 per seat per month (50% increase). Teams jumped from $12 to $20 per seat (67% increase). The free tier, which previously allowed 3 active event types, was capped at just 1. And in a move that broke workflows for Apple ecosystem users, Calendly dropped iCloud Calendar support entirely.

Per-seat pricing is especially punishing for small teams. A 5-person team on Standard now pays $720/year instead of $480 — an extra $240 annually. On Teams, the same group goes from $720 to $1,200/year, adding $480. These costs compound: every new hire doesn't just cost salary and equipment, they cost another $144-$240/year just for scheduling software. The per-seat model is designed to scale your costs with your success, ensuring you never stop paying more.

The iCloud Calendar removal is particularly telling. Calendly chose to stop supporting one of the world's most popular calendar systems. This isn't a technical limitation — it's a business decision to push users toward Google and Microsoft ecosystems where Calendly has deeper integration deals. If you're a solopreneur who runs your business from an iPhone and Mac, Calendly just told you they don't care about your workflow.