Acuity Scheduling vs Trello
Side-by-side comparison of AI visibility scores, market position, and capabilities
Online appointment booking platform for 50K+ service businesses acquired by Squarespace Apr 2019; $20-61/month with Stripe/Square payments, SMS reminders, intake forms, competing with Calendly and Vagaro for beauty/wellness/coaching scheduling aut...
About
Acuity Scheduling is an online appointment booking platform — acquired by Squarespace in April 2019 (Squarespace's first acquisition) — providing service-based businesses in wellness, beauty, coaching, tutoring, and professional services with a comprehensive scheduling solution including calendar syncing, automated email and SMS reminders, payment processing (Stripe, Square, PayPal), recurring bookings, group sessions, client intake forms, and custom branding. Founded in 2006 and supporting 50,000+ businesses at the time of acquisition, Acuity Scheduling became part of the Squarespace ecosystem as a complementary scheduling product for website builders and service businesses. In 2025, Acuity's pricing tiers range from $20/month (entry-level, 1 calendar) to $34/month (Growing, 2-6 calendars) to $61/month (Powerhouse, 36 calendars), integrated into Squarespace's website builder and commerce platform.
Visual kanban project management (Atlassian, NASDAQ: TEAM, acquired $425M 2017) with 50M+ users; May 2025 AI update adding Inbox/Planner/Mirror Cards competing with Asana and Monday.com for team workflow.
About
Trello is a visual project management and productivity platform — operating as a product of Atlassian Corporation (NASDAQ: TEAM) since its $425 million acquisition in January 2017 — providing kanban board-based task organization to over 50 million users worldwide through its boards, lists, and cards interface that applies the Kanban methodology to individual and team project tracking. Founded in 2011 by Joel Spolsky and Michael Pryor as part of Fog Creek Software (alongside Stack Overflow), Trello launched at TechCrunch Disrupt and reached 100,000 users within six weeks. Trello spun off as an independent company in 2014, raised $10.3 million in Series A from Spark Capital and Index Ventures, and was acquired by Atlassian for $425 million — the largest acquisition in Atlassian's history at the time. In May 2025, Trello launched a major platform update introducing AI-powered task extraction (automatically creating cards from conversations and documents), Trello Inbox (collecting to-dos from Slack, Microsoft Teams, and email), Trello Planner (calendar integration for deadline management), and Mirror Cards (synchronizing tasks across multiple boards).
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