Acuity Scheduling vs Chili Piper

Acuity Scheduling is an online appointment booking tool for service businesses. It was founded by Gavin Zuchlinski and acquired by Squarespace in 2019, and it is also sold inside Squarespace as Squarespace Scheduling. Clients pick a service, a staff member and a time from a booking page, fill in intake forms, pay a deposit or the full price, and receive email and SMS reminders, while the business manages availability, buffers and booking rules per staff member and location.

Beyond basic booking, Acuity handles the commercial side of appointments: packages, gift certificates, memberships and subscriptions, coupons, and payments through Stripe, Square or PayPal. Intake forms support conditional questions, which matters for clinics, therapists and coaches. Plans are tiered by the number of staff calendars: Starter (formerly Emerging) covers one, Standard (formerly Growing) up to six and Premium (formerly Powerhouse) up to 36 with multiple locations. There is a free trial but no permanent free plan.

Acuity fits salons, spas, therapists, tutors, fitness studios and consultants who sell time to individual clients. It is less suited to B2B sales teams that need round-robin routing and CRM enrichment, where Calendly or Chili Piper are stronger. Compared with Square Appointments it is more flexible on forms and packages, and compared with SimplyBook.me it offers a cleaner client experience, though its admin interface feels dated in places and SMS reminders have limits.

Chili Piper is a lead routing and meeting scheduling platform founded in 2016 in New York by Nicolas and Alina Vandenberghe. Its core job is making sure an inbound buyer who fills in a demo form is qualified, matched to the right rep and booked on that rep's calendar in seconds, instead of waiting for an email reply. Thousands of B2B go-to-market teams use it alongside Salesforce or HubSpot.

The lineup includes Form Concierge for booking straight from web forms, Chat AI that qualifies visitors and books meetings around the clock, Distro for routing leads from webinars, events and content, Handoff for SDR-to-AE booking with fairness rules, and ChiliCal for one-click scheduling links. Routing uses CRM ownership, territories, round robin, ICP scoring and enrichment from an email address, and AI agents handle spam checks and meeting prep. Pricing is now platform-based: Routing & Scheduling at $1,250 per month for 15 seats and Experiences at $3,500 per month for 30 seats, billed annually.

It fits B2B companies with real inbound volume and complex routing rules, where speed-to-lead directly drives pipeline. For simple booking pages it is overkill: Calendly and SavvyCal cost a fraction of the price and Cal.com offers routing forms with open-source flexibility. HubSpot's meetings tool may be enough for smaller HubSpot shops.

Buying tip: monthly billing is not offered, but multi-year contracts are discounted by 15% for two years, 25% for three and 40% for four, and volume discounts stack. ChiliCal is included in every seat, while standalone ChiliCal requires at least 200 users.