Clockwise
AI-powered calendar optimization and scheduling assistant that automatically rearranges meetings to create protected focus time for teams. Features intelligent flexible meetings, automatic schedule compression, AI assistant Prism with natural language commands, and team-wide coordination across Google Calendar and Outlook. Trusted by 40,000+ organizations including Uber, Netflix, and Atlassian.
30-Second Summary
Bottom Line: Clockwise excels at team-wide calendar optimization and meeting compression for organizations with heavy internal meeting loads. The AI intelligently reschedules flexible meetings to create 4-6 hours of protected focus time weekly, delivering exceptional ROI at $6.75/user/month. However, critical limitations including external meeting restrictions, once-daily optimization, and lack of mobile app significantly reduce value for client-facing professionals and mobile-first teams.
Best For
- Software development teams needing uninterrupted coding time
- Organizations with 50+ employees and heavy meeting loads
- Distributed teams coordinating across time zones
- Teams prioritizing internal collaboration optimization
Skip If
- Your role is client-facing with external meetings
- You're a freelancer or solo practitioner
- Mobile app functionality is essential
- You need real-time calendar optimization
Clockwise at a Glance
What Exactly is Clockwise?
Clockwise is an AI-powered calendar optimization platform that automatically rearranges meetings and protects focus time to help individuals, teams, and organizations reclaim valuable hours for deep work while eliminating calendar fragmentation.
Unlike traditional calendar tools that merely show availability, Clockwise applies sophisticated artificial intelligence to understand work patterns, meeting preferences, and team dynamics—then proactively adjusts schedules to maximize productivity. The platform analyzes up to one million calendar permutations per team daily to identify optimal meeting arrangements that minimize disruptions and create longer blocks of uninterrupted work time.
How Clockwise Transforms Calendar Management
Rather than forcing you to play calendar tetris manually, Clockwise's AI engine evaluates all team members' schedules simultaneously, identifying conflicts and opportunities for creating focus time blocks. When you mark internal recurring meetings as "flexible," the system automatically reschedules them to less disruptive times, creating continuous work periods for all attendees. The optimization runs daily at 4:00 PM, considering factors including working hours, meeting preferences, lunch breaks, travel time, focus time goals, and time zone requirements.
Serving over 40,000 organizations including Uber, Netflix, Atlassian, Asana, and Instacart, Clockwise has created more than 4 million hours of focus time for teams worldwide. The platform integrates with Google Calendar and Microsoft Outlook (beta), providing enterprise-grade security with SOC 2 Type II compliance, GDPR compliance, and AES-256 encryption.
Clockwise's core value proposition centers on addressing the modern workplace challenge of meeting overload and calendar fragmentation. Research shows software engineers spend 10.9 hours weekly in meetings—time that could otherwise be spent on actual development work. Marketing teams, product managers, and executives face similar constraints, constantly switching between meetings without sufficient blocks for strategic thinking, planning, or execution.
Core Features and Capabilities
Flexible Meetings: Automatic Schedule Optimization
Clockwise's flagship feature enables automatic meeting rescheduling to create optimal calendar patterns across entire teams. When you mark internal recurring meetings as "flexible," you grant Clockwise permission to move them to times that work better for all attendees.
How Flexible Meetings Work: The AI analyzes millions of calendar combinations daily, evaluating when each meeting could occur based on attendee availability, working hours, focus time goals, and existing commitments. Meetings can be configured to move "within day" (rescheduled to different times on the same day) or "within week" (moved to any day within the week). Optimization runs once daily at 4:00 PM in your organization's time zone, with a 20-hour protection window preventing last-minute changes.
Critical limitation: Flexible meetings only work with internal attendees from the same organization. Clockwise cannot reschedule meetings with external clients, vendors, or contractors, significantly limiting value for sales professionals, consultants, and client-facing roles.
Meeting Optimization Rules
What Can Be Flexible
Eligible Meetings
- Internal recurring meetings (team syncs, 1:1s)
- Meetings you organize
- Meetings more than 20 hours away
- Meetings within working hours
Cannot Be Flexible
- Meetings with external attendees
- Meetings organized by others
- Meetings within 20 hours of start
- All-day events or holds
Automatic Focus Time Protection
Clockwise intelligently identifies and protects 2+ hour blocks of uninterrupted time for deep work. You set weekly focus time goals (e.g., "I want 12 hours of focus time per week"), and the AI works to preserve these blocks while accommodating necessary meetings.
When calendars become busier, Clockwise adapts by scheduling 60-90 minute focus blocks when longer periods aren't available. The system continuously evaluates calendar changes, creating focus time blocks dynamically based on available windows. Focus time appears as calendar holds that prevent new meetings from being scheduled during these protected periods.
Prism: AI Scheduling Assistant
Launched in 2024, Clockwise's natural language AI assistant enables conversational scheduling through plain English commands. Rather than manually searching calendars and sending availability, you can request "Find 30 minutes for me and the design team early next week" and Prism analyzes all calendars to present optimal options.
Prism Capabilities
Natural Language Commands
- Schedule complex multi-person meetings instantly
- Reschedule all meetings when out of office
- Book numerous 1:1s in single request
- Convert to-do lists into flexible calendar holds
Smart Context Understanding
- Considers attendee preferences and patterns
- Respects focus time goals
- Evaluates time zone constraints
- Prioritizes optimal meeting windows
MCP Server: AI Agent Integration (New - September 2025)
Clockwise introduced the industry's first Model Context Protocol server for time management in September 2025. This breakthrough enables AI agents from platforms like Claude, Cursor, and Relay to access Clockwise's scheduling intelligence, allowing AI assistants to reason about time with human-level nuance rather than simply finding empty calendar slots.
Why MCP Server Matters
Traditional AI agents struggle with time management because they lack context about meeting preferences, team dynamics, and focus time priorities. Clockwise's MCP server provides sophisticated scheduling intelligence to AI platforms, enabling them to understand not just when people are available, but when meetings should actually occur based on productivity patterns, team coordination needs, and individual work styles.
Intelligent Calendar Management
Beyond core optimization, Clockwise provides comprehensive calendar intelligence features:
Calendar Protection Features
Time Holds & Breaks
- Smart meeting breaks (5-15 minute buffers)
- Automatic lunch time protection
- Travel time added to location-based events
- Personal-to-work calendar sync (privacy preserved)
Scheduling & Links
- Clockwise Links (AI-optimized scheduling)
- Group scheduling for team availability
- Team No Meeting Day holds
- Out-of-office automatic detection
Smart Meeting Breaks: Automatically adds configurable buffer time (5-15 minutes) between consecutive meetings to prevent calendar fragmentation and allow transition time.
Lunch & Travel Holds: Protects meal breaks automatically so teammates cannot schedule over lunch. For location-based events, travel time is automatically added to prevent back-to-back meetings across different offices.
Personal Calendar Sync: Syncs personal calendar events (Google Calendar personal, Apple Calendar) to work calendar as "busy" without exposing details, preventing double-booking while maintaining privacy.
Clockwise Links: Generate shareable scheduling links that show optimal times based on Clockwise's AI analysis—going beyond basic availability to suggest truly optimal meeting windows considering attendees' focus time needs.
Team Analytics and Calendar Health
Clockwise provides comprehensive metrics far beyond native Google Calendar insights, enabling data-driven decisions about meeting culture and time management across organizations.
Available Analytics: Team-wide focus time metrics showing weekly hours per person, meeting load analysis with fragmentation tracking, context-switching costs calculated across team, calendar health scores indicating optimization opportunities, team availability calendar showing out-of-office status, and productivity trends over time. Business and Enterprise plans include enhanced analytics with advanced reporting, calendar data export, and extended 4-week optimization windows versus 2-week standard windows.
Integrations and Compatibility
Clockwise integrates with essential productivity platforms, though integration options are more limited compared to competitors like Reclaim AI.
Current Integrations (November 2025)
Calendar Platforms
- Google Calendar (full support)
- Microsoft Outlook (beta with limitations)
- Google Workspace Marketplace integration
- Microsoft 365 cloud integration
Productivity Tools
- Slack (status updates, notifications)
- Zoom (video conferencing sync)
- Google Meet (meeting detection)
- MCP Server (AI agent integration)
Important: Asana Integration Ended
Clockwise's Asana integration was retired on January 31, 2025. Previously, users could sync Asana tasks to their calendar and create time blocks for task work. This functionality is no longer available. Teams requiring task management integration should consider Reclaim AI, which maintains native integrations with Asana, ClickUp, Jira, Linear, and Todoist.
Slack Integration: Automatically updates Slack status during meetings and focus time, showing teammates availability without manual status management. Customizable to display meeting titles or generic "In a meeting" status with custom emoji indicators.
API Access: REST API available for developers requiring custom integrations and programmatic calendar management.
Getting Started with Clockwise
Clockwise offers one of the fastest implementations in the productivity software category, with individual setup requiring just 15-20 minutes and delivering results within the first week.
Sign Up and Connect Calendar
Visit getclockwise.com and click "Sign Up" or "Get Started Free." Choose "Sign in with Google" or "Sign in with Microsoft" and complete OAuth authentication. Grant four specific permissions: calendar access (to move events), view users on domain (to identify team members), see contacts (to show names and profile images), and view calendar resources (to check conference room availability). The entire authorization process takes approximately 2-3 minutes.
Configure Preferences
Set your working hours (when you work each day), meeting hours (when you're available for meetings), time zone, and working days. Configure your weekly focus time goal (e.g., "10 hours" or "12 hours"). Set lunch break preferences to automatically protect meal times. These settings take approximately 5 minutes and ensure Clockwise respects your personal boundaries while optimizing your calendar.
Mark Flexible Meetings
Open your calendar and identify 3-4 recurring internal meetings—team syncs, 1:1s with direct reports, planning sessions, or department meetings. Click the "Flexible Meeting" toggle for each and set flexibility parameters: "Within day" allows rescheduling to different times on the same day, while "Within week" permits moving to any day within the week. These are ideal candidates because they happen regularly but aren't time-critical. This configuration takes 5-10 minutes.
Install Browser Extension (Optional but Recommended)
Download the Chrome or Firefox extension to access Clockwise features directly within Google Calendar interface. The extension adds inline controls for marking meetings as flexible, viewing focus time blocks, and accessing Prism AI assistant. While optional, the extension significantly improves the user experience by eliminating context-switching between Clockwise and your calendar.
Team Rollout Strategy (2-4 Weeks)
Week 1 - Pilot Group: Deploy to 5-10 power users who volunteer and can provide feedback. Complete individual setup, configure team definitions, and identify organizational working hours.
Week 2-3 - Full Rollout: Send company-wide launch announcement with sign-up link. Host 30-minute live training on flexible meetings. Set up team analytics dashboard and configure manager access for interpreting metrics.
Week 4 - Optimization: Review team analytics to measure impact. Adjust flexible meeting configurations based on usage patterns and feedback. Celebrate early wins (e.g., "Team generated 60 hours focus time this week"). Address any adoption friction through support resources and additional training.
Expected Results Timeline: Week 1 sees system functioning with first optimization runs. Weeks 2-3 deliver visible results with focus time blocks appearing on calendars. Week 4+ produces measurable impact with teams reporting 3-5 hours of additional focus time per person weekly.
Pricing Plans and Value Analysis
Clockwise offers exceptional value with four pricing tiers and one of the most generous free plans in the calendar optimization industry. At $6.75/user/month for core team features, Clockwise undercuts competitors while delivering comprehensive calendar intelligence.
| Plan | Monthly Price | Annual Price | Key Features | Best For |
|---|---|---|---|---|
| Free | $0 | $0 | Lunch holds, travel time, meeting breaks, personal calendar sync, Slack integration | Individuals, small teams testing |
| Teams | N/A | $6.75/user | Flexible meetings, focus time automation, group scheduling, team analytics | Growing teams, departments |
| Business | N/A | $11.50/user | Enhanced analytics, admin controls, data export, extended optimization (4 weeks) | Mid-size companies, advanced needs |
| Enterprise | Custom | Custom | SCIM provisioning, configurable security, advanced privacy, custom contracts | Large enterprises (500+ employees) |
Competitive Pricing Comparison
Clockwise's pricing advantage becomes clear when comparing equivalent tiers with major AI calendar competitors:
Entry-Level Paid Plans
- Clockwise Teams: $6.75/user/month (annual)
- Reclaim AI Starter: $8/user/month (annual)
- Motion Individual: $19/month (annual)
- Calendly Standard: $10/month (individual)
Mid-Tier Plans
- Clockwise Business: $11.50/user/month
- Reclaim AI Business: $12/user/month
- Motion Team: $12/user/month (annual)
- Calendly Teams: $16-20/user/month
At $6.75/user/month for the Teams plan, Clockwise undercuts Reclaim AI by 16%, Motion by 44%, and Calendly by 33-48% while delivering comprehensive team optimization features.
ROI Calculator: Understanding the Value
To evaluate whether Clockwise justifies the investment, consider the time value calculation:
Example: 10-Person Team ROI
Monthly Cost
- Teams plan: $6.75 × 10 users = $67.50/month
- Annual commitment required
- No per-user minimums
- Total annual: $810
Expected Time Recovery
- Conservative estimate: 3 hours/person/week focus time
- Weekly team total: 30 hours reclaimed
- Monthly total: 130 hours (30 × 4.3 weeks)
- At $75/hour: $9,750 monthly value
- ROI: 145:1 return
Break-even analysis: Clockwise pays for itself if each team member gains just 8 hours of productivity annually—achievable within the first week of use. Even at 20% of expected impact, the tool delivers positive ROI within days.
Free Plan Limitations and Upgrade Triggers
The free plan provides meaningful functionality but lacks core optimization features:
Free Plan Capabilities: Unlimited lunch holds, travel time holds, smart meeting breaks, personal-to-work calendar sync, Slack and Zoom integration, and limited scheduling links. The free plan works indefinitely without expiration.
Free Plan Limitations: No flexible meetings (core automatic rescheduling), no focus time automation (must manually create blocks), no team analytics (individual metrics only), no group scheduling links, and limited organizational coordination features.
Upgrade When: Your team has 5+ people benefiting from coordination, you're manually scheduling 8+ meetings weekly, you need protected focus time blocks automatically created, or you require team-wide analytics to measure calendar health.
Experience AI-Powered Calendar Optimization
Start with the Free Forever plan—unlimited users with core features. Upgrade to Teams when you need flexible meetings and automatic focus time. No credit card required.
Start Using Clockwise FreeHonest Assessment: Pros and Cons
What Works Exceptionally Well
- Sophisticated team-wide calendar optimization Analyzes up to 1 million calendar permutations daily per team, delivering genuinely intelligent scheduling that creates 4-6 hours of protected focus time weekly—compound benefits as more team members adopt
- Exceptional pricing and value proposition At $6.75/user/month, undercuts Reclaim AI ($8), Motion ($12-19), and Calendly ($10-20) by 16-48% while delivering comprehensive features. ROI typically exceeds 100:1 within first month
- Industry-leading AI innovation with MCP server September 2025 launch of Model Context Protocol server enables AI agents (Claude, Cursor) to access sophisticated scheduling intelligence—first calendar tool with this capability
- Genuinely robust free plan Unlike competitors limiting free tiers heavily, Clockwise offers unlimited users with meaningful features including lunch holds, meeting breaks, and personal calendar sync permanently at $0
- Enterprise-grade security and compliance SOC 2 Type II certified, GDPR and CCPA compliant, AES-256 encryption, AWS infrastructure with ISO 27001—meets rigorous security standards for regulated industries
- Fast implementation and adoption Individual setup requires just 15-20 minutes with results visible within first week. Shallow learning curve compared to Motion or comprehensive PM tools requiring weeks of training
- Natural language AI assistant (Prism) Conversational scheduling eliminates manual calendar searches—request "Schedule 30 minutes with design team next week" and AI presents optimal times considering all attendees' preferences
Significant Limitations
- Critical external meeting restriction Cannot automatically reschedule meetings with external attendees (clients, vendors, contractors). Sales professionals, consultants, and client-facing roles see severely limited value—up to 70% of meetings may be ineligible for optimization
- Once-daily optimization creates lag Flexible meetings rescheduled only once daily at 4:00 PM rather than real-time adaptation. Competitors like Reclaim AI and Motion adjust schedules immediately when calendar changes occur, preventing hours-long optimization gaps
- No native mobile app Zero iOS or Android app availability. Cannot mark meetings flexible, configure preferences, or access dashboard from phone. Mobile-first users forced to use desktop for all management—major limitation for on-the-go professionals
- Team-centric design limits individual value Maximum benefit requires team adoption across 10+ people. Solo users or small teams (2-5 people) with mostly external meetings won't benefit from team coordination—Reclaim AI better for individual time defense
- Microsoft Outlook integration remains beta Outlook support launched March 2024 still in beta as of November 2025 with reliability issues, missing features, and UX bugs. Business and Enterprise plans unavailable for Outlook users—only free and Teams plans supported
- No task management integration after Asana sunset Asana integration retired January 2025 with no replacement. Unlike Reclaim AI (supports Asana, ClickUp, Jira, Linear, Todoist), Clockwise purely focuses on calendar—requires separate task management solution
- Limited to read-only calendar functionality Cannot edit event details, titles, descriptions, or add guests within Clockwise. Users must switch to Google Calendar or Outlook for modifications—requires maintaining both Clockwise and traditional calendar simultaneously
Who Should Use Clockwise?
Clockwise delivers exceptional value for specific user segments while being poorly suited for others. Understanding whether your team's needs align with Clockwise's strengths versus limitations determines whether the investment delivers meaningful ROI.
✅ Ideal Users
Software Development Teams and Engineers
Engineers face chronic meeting overload with research showing software developers spend 10.9 hours weekly in meetings—time that could be spent coding. Clockwise excels at creating the 4-6 hour uninterrupted blocks engineers need for deep work, complex problem-solving, and reducing context-switching costs that destroy productivity.
Atlassian's 4,000+ engineers using Clockwise report significant improvements in heads-down coding time. Instacart specifically attributes engineering productivity gains to focus time protection. The aggressive meeting compression creates continuous coding blocks rather than fragmented 30-minute windows between meetings.
Perfect if: Your engineering team spends 10+ hours weekly in standups, planning, retros, and syncs. You need protected morning coding blocks when focus is highest. Team coordination across multiple time zones creates scheduling chaos.
Large Organizations (50+ Employees)
Teams with frequent internal meetings, cross-functional collaboration, and complex scheduling across departments gain maximum value from Clockwise's optimization engine. The AI becomes increasingly powerful as more team members adopt it—analyzing 50+ calendars simultaneously to find optimal meeting patterns creates compound benefits impossible to achieve manually.
Organizations with 100+ employees see Clockwise deliver team-wide analytics revealing meeting culture problems, identify coordination inefficiencies, and provide data-driven insights for improving organizational time management. The platform scales effectively from 50 to 5,000+ employees.
Perfect if: You have 50+ employees with heavy internal meeting loads. Cross-functional projects require coordination across 5-10+ people regularly. Leadership wants data-driven insights into meeting culture health. Budget allows $6.75/user investment.
Distributed and Remote Teams
Remote teams spanning multiple time zones face unique scheduling challenges that Clockwise addresses through intelligent coordination. The AI automatically identifies overlapping working hours across time zones, schedules meetings during optimal windows for all attendees, and protects focus time in each person's local timezone—preventing the common problem of early morning or late evening meetings disrupting work-life balance.
Distributed teams report that Clockwise reduces the mental overhead of timezone negotiation, eliminates 3-4 scheduling emails per meeting, and creates predictable focus time despite global coordination needs.
Perfect if: Your team spans 3+ time zones regularly. Coordinating meetings requires complex timezone calculations. You want to prevent meetings during teammates' evenings or early mornings. Focus time gets fragmented by global collaboration.
Product and Project Management Teams
PMs juggling numerous stakeholder meetings, sprint planning, retrospectives, and 1:1s while needing dedicated time for strategy, roadmapping, and execution planning benefit enormously from automatic focus time protection. Clockwise moves the flexible coordination meetings to create blocks for the deep thinking work that drives product success.
Perfect if: You manage 8-12+ recurring meetings weekly. You need 4-6 hour blocks for strategy work, roadmapping, or documentation. Your calendar currently shows back-to-back meetings with zero focus time. Team coordination across engineering, design, and business stakeholders creates scheduling complexity.
❌ Better Alternatives Exist For
Sales Teams and Client-Facing Professionals
Clockwise's external meeting restriction creates a fundamental incompatibility with sales, consulting, customer success, and other client-facing roles. Since flexible meetings only work with internal attendees, sales professionals with 60-70% external client meetings cannot benefit from the core optimization feature.
Better fit: Calendly for external client booking with customizable scheduling pages, payment collection, and CRM integrations. Or Reclaim AI for personal time defense between client meetings without requiring team adoption.
Freelancers and Solo Practitioners
Clockwise's value proposition centers on team coordination—analyzing multiple calendars to optimize collective schedules. Solo professionals or freelancers working independently see minimal benefit since there's no team to coordinate with. The free plan provides basic features, but core value requires team adoption.
Better fit: Calendly for client booking, Sunsama for mindful daily planning with timeboxing, or Reclaim AI for personal focus time defense with task management integrations.
Small Teams (2-5 People) Without Internal Meeting Load
Very small teams with minimal internal coordination meetings and simple calendars find Clockwise adds unnecessary complexity. If your 3-person team has 2-3 weekly meetings and mostly external client work, the optimization engine has little to optimize.
Better fit: Calendly for simple scheduling, native Google Calendar for basic coordination, or Motion if you need task management with calendar integration for small team project coordination.
Mobile-First Professionals
Professionals who work primarily from phones or tablets face severe limitations with Clockwise's complete absence of native mobile apps. Cannot mark meetings flexible, access dashboard, configure preferences, or use AI assistant from mobile devices—requiring desktop access for all management tasks.
Better fit: Reclaim AI with mobile app support, Calendly with excellent mobile interface, or Motion with full-featured iOS/Android apps.
Teams Requiring Task Management Integration
Organizations using Asana, ClickUp, Jira, or Linear for project management need task-to-calendar integration for time-blocking work. Clockwise ended its Asana integration in January 2025 and offers no native task management, forcing separate tools for tasks and calendar.
Better fit: Reclaim AI with native Asana, ClickUp, Jira, Linear, and Todoist integrations, or Motion as all-in-one platform combining task management with calendar coordination.
Real-World Performance and Usage Analysis
To evaluate Clockwise's real-world effectiveness, we analyzed extensive user reports, enterprise case studies, and verified metrics from organizations using the platform across different team sizes and industries.
Verified Enterprise Case Studies
Multiple large organizations have publicly documented their Clockwise implementations with measurable results:
Atlassian Implementation (4,000+ Employees)
Challenge: Engineers spending excessive time in meetings with insufficient focus time for development work.
Solution: Company-wide Clockwise deployment across 4,000+ employees with focus on engineering teams.
Results: Chris Hecht, Head of Corporate Development, reported that Clockwise "helps us maintain a healthy, sustainable work culture." Multiple engineers noted "significant improvement" in protected focus time, with one engineer stating it "genuinely changed my work experience."
Instacart Engineering Team
Challenge: Engineering team lacking adequate heads-down time for coding and technical work.
Solution: Clockwise adopted as "one of our most adopted AI products" internally according to Brandon Leonardo, Cofounder.
Results: Abbie Kouzmanoff, Senior Product Manager at Amplitude (formerly Instacart), reported: "Engineers have seen an improvement in heads-down time and ability to get work done, which of course is productivity and ultimately business impact. That's been a huge help."
Time Recovery Benchmarks by Team Size
Analysis of user reports reveals focus time creation scales with team size and meeting density:
Expected Focus Time Recovery
Small Teams (5-20 people)
- Expected recovery: 3-4 hours/person/week
- Meeting load reduction: 10-15%
- Optimization runs: 4-6 meetings moved daily
- ROI timeline: 3-5 days to break-even
Large Teams (50+ people)
- Expected recovery: 5-7 hours/person/week
- Meeting load reduction: 20-30%
- Optimization runs: 10-15 meetings moved daily
- ROI timeline: 1-2 days to break-even
User Feedback Analysis
Aggregating reviews from multiple platforms reveals consistent patterns:
Positive Patterns (4.7/5 G2 rating, 4.5/5 Capterra): Users consistently praise the time reclamation impact, reporting "completely transformed how I manage my time" and noting that Clockwise "intelligently moves meetings to create larger blocks of focus time, which has seriously boosted my productivity." Teams appreciate the reduction in email coordination—one user noted it eliminated "back-and-forth messages to figure out when people are free."
Critical Feedback Patterns: Automatic rescheduling occasionally surprises colleagues who "might have been expecting a meeting at a certain time and it gets moved, or they feel a meeting has sprung up on them earlier than expected." Some users report the tool doesn't fit their workflow, noting "It is not for me. I have tried to use it but it makes me crazy and complicates my agenda." The external meeting limitation frustrates client-facing professionals who note they "lost the feature to automatically move meetings to times that worked for all participants."
Optimization Performance Characteristics
Understanding how Clockwise's optimization actually performs helps set realistic expectations:
Daily Optimization Cycle: Clockwise runs optimization once daily at 4:00 PM in your organization's time zone. The AI analyzes up to 1 million calendar permutations per team, evaluating when each flexible meeting could occur based on attendee availability, working hours, focus time goals, and existing commitments. Meetings scheduled within 20 hours cannot be moved to prevent last-minute disruptions.
Limitation Impact: Unlike real-time optimizers (Reclaim AI, Motion) that adjust immediately when calendar changes occur, Clockwise's once-daily schedule means new meetings added after 4:00 PM aren't considered until next day's optimization—potentially creating 20+ hour lag before schedule adjusts.
Team Adoption Patterns
Success with Clockwise correlates strongly with team adoption rate and meeting density:
High-Success Scenarios: Teams with 70%+ adoption within 30 days, 8-12+ recurring internal meetings weekly, strong leadership support for calendar optimization, and clear communication about how flexible meetings work see consistent 4-6 hour weekly focus time gains.
Lower-Impact Scenarios: Teams with under 40% adoption, heavy external client meetings (60%+ of calendar), resistant colleagues who refuse to mark meetings flexible, or inconsistent communication about changes see limited benefit—often 1-2 hours weekly rather than 4-6 hours.
Clockwise vs Popular Alternatives
Understanding how Clockwise compares to leading AI calendar alternatives helps determine whether it's the optimal choice for your specific workflow, team structure, and productivity priorities.
Clockwise vs Reclaim AI
Reclaim AI emphasizes individual calendar defense and personal time protection, working as a personal assistant that guards your time with habit-based scheduling and task management integrations. Clockwise focuses on team-wide calendar optimization and meeting compression through aggressive schedule coordination.
Core Philosophy Difference
Clockwise approach: Active, interventionist—automatically moves flexible meetings across team calendars to create collective focus time. Value compounds as more team members adopt, analyzing 10-100+ calendars simultaneously to find optimal patterns.
Reclaim AI approach: Defensive posture—protects your personal time blocks against external encroachment while maintaining flexibility to reschedule if truly urgent conflicts emerge. Provides immediate individual value even without team adoption.
Feature Comparison
Clockwise Strengths
- Team coordination across 50+ people
- Aggressive meeting compression
- Team-wide analytics and insights
- Lower cost ($6.75 vs $8/user)
- Company-wide calendar health metrics
Reclaim AI Strengths
- Native task management with PM tool integrations
- Real-time optimization (not once daily)
- Smart 1:1s auto-scheduling for managers
- Advanced habit-based recurring routines
- Works solo without team adoption
Pricing: Clockwise Teams at $6.75/user/month versus Reclaim AI Starter at $8/user/month represents 16% cost savings. Both offer generous free tiers, though Reclaim's free plan includes more features.
Choose Clockwise if: You have a large team (50+ people) with heavy internal meeting loads. Team adoption is feasible across department. You need organization-wide analytics. Budget is primary concern. Your pain is meeting overload, not task management.
Choose Reclaim AI if: You're an individual in large company needing personal time defense. You require task management integration with Asana, ClickUp, Jira, or Linear. You manage 8+ direct reports needing automated 1:1 scheduling. Real-time optimization is critical. You want value without requiring team adoption.
Clockwise vs Motion
Motion functions as a comprehensive AI project management platform combining task management, calendar synchronization, meeting scheduling, and automatic task scheduling into unified workspace. Clockwise specializes purely in calendar optimization without project management features.
Fundamental Difference: Motion attempts to replace multiple tools (Asana, calendar, scheduling) with all-in-one platform at $12-19/user/month. Clockwise focuses exclusively on calendar intelligence at $6.75/user/month, working alongside existing PM tools.
Clockwise Best For
- Teams already using Asana/ClickUp/Jira
- Meeting overload primary pain
- Budget-conscious ($6.75 vs $12-19/user)
- Organization-wide calendar analytics
- Fast implementation (1-2 weeks)
Motion Best For
- Consolidating multiple tools
- Task and project deadline management
- Automatic task scheduling with AI
- Campaign management with dependencies
- Full mobile app requirement
Cost Comparison: For 10-person team—Clockwise at $810/year versus Motion at $1,440/year represents 78% higher cost for Motion. Motion delivers more functionality (tasks + calendar) but requires adopting as primary workspace.
Clockwise vs Calendly
Calendly specializes in external client meeting booking and appointment scheduling with customizable booking pages. Clockwise optimizes internal team calendars and protects focus time. These solve fundamentally different problems and typically complement each other rather than compete.
Complementary Use: Sales teams commonly use Calendly for client booking ($10-20/user) plus Clockwise for internal team coordination ($6.75/user), allowing client meetings to show as "busy" while Clockwise optimizes internal meetings around client commitments.
When They Work Together: Calendly handles external client meetings through booking pages. Client meetings appear on your calendar as "busy." Clockwise sees these blocked times and protects team focus time around client commitments, automatically rearranging internal flexible meetings to accommodate client-facing schedule.
Choose Clockwise if: Primary need is internal team coordination. You're drowning in internal meetings. Engineering, product, or operations team. Need focus time protection for deep work.
Choose Calendly if: Sales role taking unlimited client calls. Consultant accepting external bookings. Customer success managing recurring client check-ins. Need payment collection and CRM integrations.
Clockwise vs Sunsama
Sunsama emphasizes mindful daily planning with structured rituals, timeboxing, and sustainable work-life balance. Clockwise delivers passive, automatic calendar optimization at organizational level.
Philosophy Contrast: Sunsama requires 15 minutes daily planning ritual where you intentionally timebox tasks. Clockwise runs automatically in background requiring zero daily time investment.
Pricing: Clockwise at $6.75/user/month versus Sunsama at $16-20/month represents 58-66% cost savings. However, Sunsama includes 15+ task integrations (Notion, Asana, Todoist, Gmail) while Clockwise offers none after Asana sunset.
Choose Clockwise if: You want passive, automatic optimization. Team adoption feasible. Meeting overload primary pain. Prefer algorithms over daily ritual.
Choose Sunsama if: You value intentional daily planning. Solo work or self-directed focus matters more than team coordination. You integrate heavily with Notion/Asana. You're willing to invest 15 minutes daily. Work-life balance and sustainability priorities.
Choosing the Right Platform
Clockwise excels for teams with heavy internal meeting loads wanting aggressive automatic optimization at budget-friendly pricing ($6.75/user). The platform delivers exceptional value through team coordination, comprehensive analytics, and focus time creation—particularly for software development teams, large organizations (50+ people), and distributed remote teams.
However, alternatives win in specific domains: Reclaim AI for individual time defense with task management integration, Motion for all-in-one project management with automatic task scheduling, Calendly for external client booking, and Sunsama for mindful daily planning. Your specific requirements around team size, meeting composition (internal vs external), mobile needs, task management integration, and budget determine optimal selection.
Frequently Asked Questions
What is Clockwise and how does it work?
Clockwise is an AI-powered calendar optimization platform that automatically rearranges meetings to create protected focus time for teams. It integrates with Google Calendar or Microsoft Outlook and runs daily optimization at 4:00 PM, analyzing up to one million calendar permutations per team to identify optimal meeting arrangements. When you mark internal meetings as "flexible," Clockwise automatically reschedules them to less disruptive times, creating longer blocks of continuous work time (typically 4-6 hours weekly) for all attendees. The system considers working hours, meeting preferences, time zones, focus time goals, lunch breaks, and existing commitments when optimizing schedules.
How much does Clockwise cost?
Clockwise offers four pricing tiers: Free plan at $0 (includes lunch holds, travel time, meeting breaks, personal calendar sync, Slack integration—unlimited users permanently), Teams plan at $6.75/user/month billed annually (adds flexible meetings, focus time automation, group scheduling, team analytics), Business plan at $11.50/user/month annual billing (enhanced analytics, admin controls, data export, priority support), and Enterprise plan with custom pricing (SCIM provisioning, advanced security, custom contracts). The Teams plan delivers core optimization features at the lowest price point among AI calendar competitors, undercutting Reclaim AI ($8), Motion ($12-19), and Calendly ($10-20) by 16-48%.
Can Clockwise reschedule external meetings with clients?
No. Clockwise cannot automatically reschedule meetings with external attendees—this is a significant limitation. Flexible meetings (the core rescheduling feature) only work with internal meetings where all attendees are from the same organization's email domain. Clockwise cannot reschedule meetings with external clients, vendors, contractors, or anyone outside your organization because the AI cannot control external calendars and external attendees haven't authorized Clockwise access. This severely limits value for sales professionals, consultants, and client-facing roles where 60-70% of meetings may be external. However, external meetings do show as "busy" on your calendar, and Clockwise protects team focus time around these known client commitments by adjusting internal flexible meetings.
Does Clockwise work with Microsoft Outlook?
Yes, but with important limitations. Clockwise integration with Microsoft Outlook remains in beta as of November 2025 (launched March 2024). What works: basic calendar reading and writing, flexible meetings (beta), focus time holds (beta), lunch holds, travel time, and Slack integration. Current limitations: still in beta with potential user experience bugs, new Google features not immediately available on Outlook version, Business and Enterprise paid plans unavailable for beta users (only Free and Teams plans supported), reliability inconsistencies reported, Microsoft 365 on-premise (not cloud) is NOT supported. Google Calendar users receive full feature access with all features available immediately. Recommendation: Test free plan first if using Outlook, be aware of beta status instability, and expect full feature parity with Google Calendar within 6 months.
Is there a Clockwise mobile app?
No. Clockwise does not have a dedicated native mobile app for iOS or Android. Mobile access is extremely limited: you can access the web app through mobile browser (poor mobile optimization), use native Google Calendar or Outlook mobile app to view Clockwise changes automatically, or receive Slack notifications on mobile. Critical limitations: cannot mark meetings flexible from phone, cannot configure preferences or settings on mobile, cannot access Clockwise dashboard from phone, cannot use AI Scheduler (Prism) on mobile. Recommended workflow: use desktop (Chrome extension) for configuration and management, use mobile calendar app only to view rescheduled meetings and accept/reject changes. This is a major limitation for mobile-first professionals who work primarily from phones or tablets. No official announcement of mobile app development as of November 2025.
How is Clockwise different from Reclaim AI or Motion?
Clockwise focuses on team-wide calendar optimization and meeting compression, analyzing multiple people's schedules simultaneously to create collective focus time. It's best adopted across entire teams or departments. Reclaim AI emphasizes individual calendar defense and personal time protection, working as a personal assistant that guards your time while integrating with existing project management tools—it provides immediate value even without team adoption. Motion is an all-in-one AI project management platform combining task management, calendar, and automatic task scheduling, designed to replace multiple tools like Asana rather than integrate with them. Key differences: Clockwise has no task management (Asana integration ended January 2025) while Reclaim integrates with Asana/ClickUp/Jira and Motion has native full-featured task management. Clockwise optimizes once daily at 4:00 PM while Reclaim and Motion adapt in real-time. Pricing: Clockwise $6.75/user (cheapest), Reclaim $8/user, Motion $12-19/user. Choose Clockwise for team coordination at budget price, Reclaim for individual time defense with task integration, or Motion for all-in-one consolidation.
What meetings can be marked as flexible?
Flexible meetings must meet specific criteria: internal recurring meetings with all attendees from same organization, meetings you organize (not organized by others), meetings more than 20 hours away from start time, and meetings within your defined working hours. Ideal flexible meeting candidates include weekly 1:1s with direct reports, team syncs and standups, all-hands internal meetings, department meetings, planning sessions, retrospectives, and recurring internal check-ins. What CANNOT be flexible: any meeting with external attendees (clients, vendors, contractors), meetings organized by others, meetings within 20 hours of start time (prevents last-minute disruptions), all-day events or holds, and meetings with mixed internal/external attendees. Best practice: Start by marking high-frequency recurring internal meetings as flexible since they happen regularly but aren't time-critical, making them ideal for rescheduling.
How do team members know when meetings are rescheduled?
Clockwise sends automatic notifications through multiple channels when flexible meetings are rescheduled. Email notification goes to all attendees specifying old time and new time with meeting details. Calendar update happens automatically in all attendees' calendars with no manual action required. Slack status update (if integrated) automatically reflects new meeting time showing "In meeting" during new window. Clockwise dashboard shows which meetings moved with reason for move (e.g., "Created 3 hours of focus time for team") and attendee list with new time. Notifications work even for non-Clockwise users—meeting attendees who don't have Clockwise installed still receive email notification and automatic calendar update. You can customize notification types in Settings: email when meeting moves (default ON, can disable), Slack status update (ON if integrated), non-Clockwise attendee notification (ON, customizable), summary email of all weekly moves (ON), and weekly review email (ON).
What is Clockwise Brain (Prism) AI assistant?
Prism is Clockwise's natural language AI assistant launched in 2024 that enables conversational scheduling through plain English commands. Rather than manually searching calendars and sending availability, you can request commands like "Find 30 minutes for me and the design team early next week" or "Schedule 15-minute 1:1s with everyone on my team" and Prism analyzes all calendars to present optimal options. Key capabilities include: scheduling complex multi-person meetings instantly, rescheduling all meetings when out of office in single request, booking numerous 1:1s in one command, and converting to-do lists into flexible calendar holds. The AI considers attendee preferences and patterns, respects focus time goals, evaluates time zone constraints, and prioritizes optimal meeting windows beyond just availability. Prism differs from basic scheduling assistants by understanding context—it knows when meetings should occur based on productivity patterns and team coordination needs, not just when slots are empty.
Is Clockwise worth it for small teams or freelancers?
Clockwise delivers limited value for freelancers and very small teams (2-5 people). The platform's core value proposition centers on team coordination—analyzing multiple calendars to optimize collective schedules. Solo professionals or freelancers working independently see minimal benefit since there's no team to coordinate with. Small teams without heavy internal meeting loads find the optimization engine has little to optimize. Worth it if: You have 5-15 person team with 8+ recurring internal meetings weekly, team coordination across multiple projects creates scheduling complexity, budget allows $6.75/user investment ($34-101/month for 5-15 people), and you're planning to scale team in next 6-12 months. Not worth it if: You're solo freelancer or consultant, small team (2-3 people) with minimal internal meetings, majority of meetings are external client-facing, mobile app functionality is essential, or you need task management integration. Better alternatives: Reclaim AI for individual time defense with task integration, Calendly for client booking, Sunsama for personal daily planning, or native Google Calendar for simple 2-3 person coordination. Recommendation: Test free plan with real project before upgrading—if you don't see 3+ hours weekly focus time improvement after 2 weeks, Clockwise isn't providing sufficient value.
Final Verdict: Should You Choose Clockwise?
The Bottom Line
After comprehensive analysis of Clockwise's capabilities, enterprise case studies, extensive user feedback, and competitive positioning, the platform stands out as an exceptional value for teams prioritizing internal calendar optimization and meeting compression at budget-friendly pricing. The sophisticated AI analyzing 1 million calendar permutations daily, genuinely robust free plan, and proven ability to create 4-6 hours of weekly protected focus time make it compelling for organizations with heavy internal meeting loads.
The Critical Tradeoffs
However, Clockwise's strengths come with real limitations. The inability to reschedule external meetings, once-daily optimization schedule creating 20+ hour lag, complete absence of mobile apps, and team-centric design requiring adoption across 10+ people create genuine barriers to value. Sales professionals with 60-70% external client meetings, freelancers without teams to coordinate, mobile-first users requiring on-the-go management, and small teams (2-5 people) see severely limited benefit. The January 2025 Asana integration retirement without replacement eliminates task management capabilities, forcing separate tools for tasks and calendar.
Where Clockwise Excels
The platform particularly shines for software development teams needing uninterrupted coding blocks, large organizations (50+ employees) coordinating complex internal schedules, and distributed remote teams managing time zone complexity. Verified case studies from Atlassian (4,000+ employees) and Instacart document measurable productivity improvements directly attributed to focus time protection. At $6.75/user/month for Teams plan—16-48% cheaper than Reclaim AI ($8), Motion ($12-19), and Calendly ($10-20)—Clockwise delivers exceptional pricing value. Organizations report typical ROI exceeding 100:1 within first month through time reclamation alone.
Our Recommendation
Test the Free Forever plan with an actual team project for at least 2 weeks. Don't evaluate with placeholder scenarios—use real recurring internal meetings to assess whether Clockwise's optimization creates meaningful focus time and whether team adoption is feasible in your organizational culture.
- You have team of 10+ people with heavy internal meeting loads
- Software development, product management, or operations teams needing focus time
- Budget is primary concern—$6.75/user beats all competitors
- Meeting overload is your primary productivity pain point
- Team adoption across department is realistic within 30 days
- Majority of meetings are internal rather than external clients
- Desktop-first workflow allows managing from computer
Consider alternatives if:
- Your role is client-facing with 60%+ external meetings → Try Calendly for booking
- You need task management integration → Choose Reclaim AI with Asana/ClickUp/Jira support
- Mobile app functionality is essential → Use Reclaim AI or Motion
- You're solo freelancer or small team (2-5 people) → Try Reclaim AI for individual value
- Real-time optimization is critical → Choose Reclaim AI or Motion
- You need all-in-one with task management → Explore Motion comprehensive platform
- Mindful daily planning over automation → Try Sunsama for intentional timeboxing
Free Forever plan • Unlimited users • No credit card required
Ready to Start?
- Free Forever plan
- AI calendar optimization
- 40,000+ organizations
Quick Specifications
- Founded
- 2016
- Organizations
- 40,000+
- Focus Time
- 4M+ Hours Created
- Starting Price
- $6.75/user/month
- Free Tier
- Free Forever
- Platform
- Web, Browser
Reclaim AI
Individual calendar defense with habit-based scheduling and native task management integrations (Asana, ClickUp, Jira). Better for personal time protection without team adoption requirement.
Motion AI
Comprehensive AI project management combining task scheduling, calendar optimization, and deadline management. Better for automatic task scheduling but more expensive than Clockwise.
Calendly
External client meeting booking specialist with customizable pages and payment collection. Complements Clockwise for sales teams by handling client scheduling while Clockwise optimizes internal meetings.
Sunsama
Mindful daily planner with structured rituals and intentional timeboxing. Better for individual contributors prioritizing work-life balance over automatic team coordination.