Calendly vs When I Work

Calendly is a scheduling tool that lets people offer booking pages and coordinate meetings across calendars. It supports one-on-one, group, collective, multi-host, round-robin, and team scheduling, with two-way calendar sync and automated reminders. Users can collect payments through Stripe and PayPal; payment tools also include links, packages, and invoices. The always-free plan allows one event type, one calendar connection, and one-on-one scheduling, and signup does not require a credit card. Standard costs $10 per seat per month billed yearly, while Teams costs $16 per seat per month billed yearly; both list up to six calendars per user. The service is available through mobile apps and a browser extension, and lists more than 150 integrations, including Google Calendar, Microsoft Teams, Outlook, Zoom, HubSpot, Mailchimp, and Zapier. Teams adds administration features such as team groups, admins, and centrally managed events. Enterprise lists SSO, SAML, domain control, audit log compliance, a data deletion API, dedicated account support, onboarding, and implementation. Calendly was founded in 2013 and is headquartered in Buford, Georgia.

When I Work brings employee scheduling, shift swaps, team messaging, and time tracking together for shift-based workplaces. Auto scheduling assigns shifts using staff availability and qualifications, and managers can oversee multiple stores, departments, or job sites from one dashboard. The time clock tracks attendance, breaks, and time off, while staff can message without sharing phone numbers. It runs on the web, Android, and iOS. Essentials costs $2.50 a month billed per user per month; Pro is $5 a month billed per user per month; Premium is $8 a month billed per user per month. A 14-day trial offers complete access and requires no credit card, but there is no free plan. API key access, webhooks, and SAML/SSO are included in Premium. When I Work says it uses AWS, TLS, daily backups, multiple-disk writes, and mobile two-step verification. It does not offer an SLA, although its hosting partners guarantee 99.9% uptime.