Two different types of scheduling software

“Scheduling software” covers two different categories that get conflated:

Appointment scheduling: Tools that let clients or customers book time with you or your team — consultations, service appointments, meetings. Think Calendly, Acuity, or Booksy.

Team/workforce scheduling: Tools that manage when employees work — shift scheduling, availability management, time-off requests. Think When I Work, Homebase, or Deputy.

Identify which problem you’re actually trying to solve before evaluating tools.

Appointment scheduling tools

Calendly ($0–16/user/month): The most widely known option. Share a link; the person picks a time from your available slots. Integrates with Google Calendar, Outlook, Zoom, and most CRM platforms. Free tier works for one event type and one calendar. Professional plan ($12/month) adds multiple event types, group scheduling, and automations.

Acuity Scheduling ($16–49/month): More customization than Calendly. Client self-scheduling, intake forms before appointments, payment collection at booking, package and subscription sales. Better for service businesses (salons, coaches, therapists) that need more than simple meeting scheduling.

Square Appointments (free for individuals): Included with Square if you process payments through Square. Full appointment booking, client management, and automated reminders. The obvious choice if you’re already using Square.

Booksy (service-based businesses): Designed for beauty, wellness, and personal service businesses. Customer-facing marketplace in addition to direct booking link.

Team scheduling tools

Homebase (free for one location): Time tracking, shift scheduling, and team communication in one tool. The free tier is generous and covers most small business needs. Works well for retail, food service, and service businesses with hourly employees.

When I Work ($2.50–6/user/month): Slightly more polished than Homebase for scheduling. Good for teams of 5–100. Scheduling, time clock, team messaging.

Deputy ($3.50/user/month): More robust for compliance-heavy environments (labor law break rules, overtime alerts). Better for larger teams or businesses in states with complex scheduling regulations.