Reclaim.ai

Overview

Reclaim.ai is an AI-powered calendar assistant founded in 2019 that automatically defends focus time and optimizes meeting schedules for teams with heavy calendar loads. The platform uses machine learning to block recurring deep work time (habit scheduling), auto-book 1:1 meetings when both calendars align (smart 1:1s), and enforce buffer time policies (prevent back-to-back meetings).

Core capabilities:

• Habit Scheduling: Automatically defend recurring focus blocks (e.g., "Block 2 hours every Tuesday/Thursday 9-11am for strategic work") - reschedules dynamically when meetings conflict
• Smart 1:1 Meetings: Auto-coordinate recurring check-ins by finding mutual availability across both calendars without Calendly back-and-forth
• Task Scheduling: Block calendar time for task completion based on due dates and priority (syncs with Asana, Linear, Jira)
• Buffer Time Policies: Enforce 10-30 min breaks before/after meetings to prevent back-to-back scheduling burnout
• Multi-Calendar Sync: Merge work + personal calendars to show true availability (paid plans only)
• Time Tracking: Measure actual time spent in meetings vs focus work vs breaks

Typical use case: A sales leader with 25 meetings/week spends 6 hours/week on calendar Tetris (moving focus time around new meeting requests, finding 1:1 slots with reps, scheduling strategic planning blocks). After setting up Reclaim.ai habits ("Block 3 hours Friday morning for quarterly planning" + "Schedule 30min 1:1s with 8 direct reports weekly"), the AI automatically defends focus blocks, reschedules habits when urgent meetings arise, and books 1:1s when both calendars show mutual free time → Saves 6 hours/week on calendar management while protecting 40% of calendar for non-meeting work.

Reclaim.ai differentiates via AI-driven calendar optimization (vs manual booking link management with Calendly/Cal.com). The platform focuses on internal scheduling (protect your own time, coordinate team 1:1s) vs external booking (prospects scheduling demos with you).

Used by 30,000+ teams including sales leaders (defend focus time from meeting overload), SDR managers (auto-book recurring rep 1:1s), customer success (prevent back-to-back client calls), and RevOps (protect project work blocks).

Cost comparison (time-saved value):

• Manual calendar management: 6-8 hours/week for sales leader with 25 meetings/week
• Reclaim.ai Business ($12/user): Automates habit defense, smart 1:1s, buffer policies → Saves 6-8 hours/week
• ROI: $12/month = $0.40/day vs $200-400/day value of 6-8 saved hours (assuming $50/hour fully-loaded cost) = 500-1000x ROI

Free tier value:

• Unlimited habits (defend recurring focus blocks without paying)
• Unlimited tasks (schedule task completion in calendar)
• Unlimited scheduling links (external booking like Calendly)
• Smart 1:1s (auto-book recurring team meetings)
• Perfect for: Individual contributors testing AI calendar optimization before team rollout

Best value: Business $12/user for teams with 5-50 people needing shared calendar policies (e.g., "No meetings before 10am company-wide", "Enforce 15min buffer between all meetings"). Starter $8/user sufficient for individuals only needing multi-calendar sync (work + personal merged).

When to upgrade:

• Free → Starter ($8): When you need to merge work + personal calendars to show true availability (prevent double-booking across multiple calendars)
• Starter → Business ($12): When you need team scheduling (shared habits, collective events, buffer policies enforced company-wide)
• Business → Enterprise (custom): When you reach 100+ users and need SSO, dedicated support, advanced analytics

1. Habit Scheduling (Defend Focus Time)

Reclaim.ai's habit scheduling automatically defends recurring focus blocks from meeting creep by dynamically rescheduling habits when conflicts arise.

How it works:

1. Create habit: "Block 2 hours every Tuesday/Thursday 9-11am for strategic planning"
2. Reclaim.ai defends time: Blocks appear in Google Calendar as "Strategic Planning (Habit)"
3. Conflict resolution: Urgent meeting request arrives for Thursday 10am → Reclaim.ai automatically moves habit to Thursday 2-4pm (next available 2-hour slot)
4. Reschedule notification: "Habit 'Strategic Planning' moved from 9-11am to 2-4pm due to new meeting"

Habit types:

• Focus time: Deep work blocks (2-4 hours) for project work, strategic planning, content creation
• Personal time: Lunch breaks (30-60 min), exercise (1 hour), commute time (30 min)
• Learning time: Training blocks (1-2 hours), reading industry news (30 min), skill development (1 hour)
• Admin time: Email processing (1 hour), expense reports (30 min), CRM updates (1 hour)

Typical use case: SDR manager with 5 direct reports schedules 25 meetings/week (team 1:1s, pipeline reviews, coaching sessions) → Previously spent 4 hours/week manually moving "Friday strategic planning" block around new meeting requests. After creating Reclaim.ai habit ("Block 3 hours every Friday 9am-12pm for quarterly planning"), AI automatically defends Friday mornings, reschedules when urgent meetings conflict, and notifies manager of changes → Saves 4 hours/week on calendar Tetris while ensuring strategic planning always gets protected time.

Habit defense priority:

• High priority: Meetings with external participants (can't be moved easily)
• Medium priority: Internal team meetings (can be rescheduled with coordination)
• Low priority: Habits (flexible, Reclaim.ai moves automatically to next available slot)

Limitation: Habits only reschedule within same week by default (if Thursday habit can't be moved, Reclaim.ai won't automatically push to next week). Requires manual intervention to skip/reschedule habits across weeks.

2. Smart 1:1 Meetings (Auto-Coordinate Recurring Check-Ins)

Reclaim.ai's smart 1:1s automatically book recurring check-ins by finding mutual availability across both calendars without manual Calendly coordination.

How it works:

1. Create smart 1:1: "Weekly 30min check-in with Sarah (SDR)" → Set cadence (weekly), duration (30 min), priority (medium)
2. Reclaim.ai finds mutual time: Scans both calendars for mutual free slots (considers existing meetings, habits, buffer time)
3. Auto-book meeting: Books next available slot where both calendars show 30min mutual availability (e.g., Tuesday 2pm)
4. Reschedule automatically: If conflict arises (Sarah gets urgent meeting Tuesday 2pm), Reclaim.ai moves 1:1 to next mutual slot (Wednesday 10am) and notifies both parties

Smart 1:1 benefits vs manual Calendly:

• No back-and-forth: Eliminates "When are you free this week?" Slack messages + Calendly link sharing
• Respects habits: Won't book 1:1s during either person's defended focus time
• Buffer time aware: Enforces 15min buffer if enabled (won't book 1:1 immediately after other meetings)
• Recurring coordination: Auto-books all future 1:1s (no need to coordinate every week)

Typical use case: Sales leader with 8 direct reports previously spent 2 hours/week coordinating 8 weekly 1:1s via Slack ("When's good for our check-in?") + Calendly links. After setting up 8 smart 1:1s in Reclaim.ai (30 min weekly with each rep), AI automatically books all 8 meetings when both calendars align, reschedules when conflicts arise, and sends notifications → Saves 2 hours/week on 1:1 coordination while ensuring all check-ins happen consistently.

Smart 1:1 priority settings:

• High priority: CEO 1:1s, skip reports (Reclaim.ai protects these slots aggressively)
• Medium priority: Direct report 1:1s, peer check-ins (can be rescheduled if urgent meetings arise)
• Low priority: Optional sync meetings, informal coffee chats (easily moved when conflicts occur)

Limitation: Both participants must use Reclaim.ai + Google Calendar (if counterpart uses Outlook, smart 1:1s won't work - use Calendly instead).

3. Buffer Time Policies (Prevent Back-to-Back Meetings)

Reclaim.ai's buffer time policies enforce 10-30 minute breaks before/after meetings to prevent back-to-back scheduling burnout.

How it works:

1. Set buffer policy: "Enforce 15min buffer before and after all meetings"
2. Reclaim.ai blocks buffer time: If meeting scheduled 2-3pm, Reclaim.ai blocks 1:45-2pm (before) and 3-3:15pm (after) as "Buffer Time"
3. Prevent overlaps: New meeting requests for 1:45pm get rejected (buffer time protected), prospects see next available slot as 3:30pm
4. Buffer exceptions: Override for urgent meetings (manually accept meeting during buffer time if needed)

Buffer time benefits:

• Prevent burnout: Avoid 8-hour days of back-to-back Zoom calls (common for sales/CS roles)
• Prep/debrief time: Use 15min before meeting to review notes, 15min after to log CRM notes
• Context switching: Mental break between topics (switch from demo to internal pipeline review)
• Bathroom breaks: Practical benefit of not being trapped in back-to-back calls

Typical use case: Customer success manager booking 40 client calls/week (8 calls/day × 5 days) experiences burnout from back-to-back Zoom marathon (8am-5pm straight calls). After enabling 15min buffer policy, Reclaim.ai automatically limits schedule to 28-32 calls/week (56-64 hours → 42-48 hours with buffers), creating breathing room between calls → Reduces burnout while maintaining 70-80% of previous meeting volume.

Buffer policy options:

• 10 minutes: Minimal buffer (just enough for bathroom break)
• 15 minutes: Standard buffer (debrief + prep time)
• 30 minutes: Generous buffer (deep prep for complex meetings)

Buffer policy scope:

• All meetings: Apply buffer to every calendar event (most aggressive protection)
• External only: Buffer only for meetings with external participants (preserve flexibility for internal quick syncs)
• Specific meeting types: Buffer only for demos, client calls, interviews (exclude internal team meetings)

Limitation: Buffer policies can reduce total meeting capacity by 20-30% (if you currently book 40 meetings/week, buffers may limit to 28-32 meetings). Not ideal for high-volume transactional sales roles (SDRs doing 50+ cold calls/day).

4. Multi-Calendar Sync (Work + Personal)

Reclaim.ai's multi-calendar sync (Starter plan $8/user) merges work + personal calendars to show true availability and prevent double-booking.

How it works:

1. Connect multiple calendars: Link Google Workspace (work) + personal Google Calendar to Reclaim.ai
2. Merge availability: Reclaim.ai reads events from both calendars (sees personal dentist appointment 2pm, work team meeting 3pm)
3. Block unified time: When creating scheduling links, Reclaim.ai shows only slots free on BOTH calendars (prevents prospects booking demo during personal appointment)
4. Privacy protection: Personal calendar events appear as "Busy" blocks in work calendar (titles/details hidden)

Multi-calendar benefits:

• Prevent double-booking: No more accepting work meeting during personal dentist appointment
• Work-life boundaries: Defend personal time (kids' soccer game, gym session) from work meeting creep
• True availability: Scheduling links show only genuinely free time (no manual calendar coordination)

Typical use case: Sales rep with personal appointments (gym 6-7am, kids' pickup 3-4pm, evening classes Tuesday/Thursday 6-8pm) previously got booked for demos during personal commitments because prospects only saw work calendar availability. After connecting personal calendar to Reclaim.ai, scheduling links automatically exclude personal commitment times → Prevents 3-5 conflicts/month and protects work-life balance.

Privacy controls:

• Show as busy: Personal events appear as "Busy" in work calendar (no details visible to colleagues)
• Title masking: Replace personal event titles with generic "Personal Time" in work calendar view
• Selective sync: Choose which personal calendars to merge (e.g., sync personal appointments but not family member calendars)

Limitation: Requires all calendars to be Google Calendar (can't sync Outlook personal + Google Workspace work). Multi-calendar sync costs $8/user/month (not available on free tier).

5. Task Scheduling (Auto-Block Completion Time)

Reclaim.ai's task scheduling automatically blocks calendar time for task completion based on due dates and priority.

How it works:

1. Add task: "Prepare Q1 sales deck" → Set due date (Friday), estimated time (3 hours), priority (high)
2. Reclaim.ai schedules time: Finds 3-hour slot before Friday deadline when calendar shows availability (e.g., Thursday 1-4pm)
3. Block calendar: Creates "Task: Prepare Q1 sales deck" calendar event Thursday 1-4pm
4. Reschedule dynamically: If meeting request arrives for Thursday 2pm, Reclaim.ai moves task to Thursday 9am-12pm or Wednesday afternoon

Task scheduling benefits:

• Guaranteed completion: Ensures high-priority tasks get calendar time (vs hoping to "find time later")
• Deadline protection: Automatically schedules task blocks before due dates (prevents last-minute scramble)
• Visual workload: See task blocks in calendar alongside meetings (total time commitment visible at glance)

Task integrations:

• Asana: Sync Asana tasks to Reclaim.ai, auto-schedule completion blocks based on due dates
• Linear: Import Linear issues, block dev time in calendar when issues assigned to you
• Jira: Sync Jira tickets, schedule sprint work based on story points + deadlines

Typical use case: RevOps analyst with 15 ongoing projects (dashboard builds, data analysis, process documentation) struggles to find time for deep work between 20 meetings/week. After adding 10 high-priority tasks to Reclaim.ai (2-4 hours each), AI automatically schedules 20 hours/week of project blocks in calendar → Ensures project work gets protected time vs getting pushed out by meetings.

Limitation: Task scheduling requires estimating time accurately (if you estimate 2 hours but task takes 4 hours, Reclaim.ai won't automatically extend block). Works best for recurring similar tasks where estimates improve over time.

Choose Reclaim.ai if:

• You use Google Calendar exclusively (no Outlook requirement)
• You need smart 1:1 auto-coordination (eliminates Calendly coordination overhead)
• You want free tier ($0 unlimited habits/tasks to test before team rollout)
• You're budget-conscious ($0-12/user vs Motion $19-34/user = save 42-185%)
• You focus on calendar optimization only (don't need comprehensive task/project management)

Choose Motion if:

• You use Microsoft Outlook/Office 365 (Reclaim.ai doesn't support)
• You need task + project management (Motion auto-schedules tasks based on priority/dependencies/deadlines)
• You want comprehensive productivity suite (calendar + tasks + projects in one tool vs Reclaim's calendar-only focus)
• You can justify $19-34/user premium (42-185% more expensive than Reclaim but more features)

Startups (5-15 people)

Best plan: Free ($0/month) or Starter ($8/user) Why: Test habit scheduling on free tier (unlimited habits/tasks), upgrade to Starter when team needs multi-calendar sync (work + personal merged).

Use case: 5-person sales team with founder doing 30 meetings/week (loses 6 hours/week to calendar Tetris) sets up Reclaim.ai habits ("Block 3 hours Friday morning for strategic planning" + "Schedule 30min weekly 1:1s with 4 reps") → AI automatically defends focus time and coordinates 1:1s → Saves founder 6 hours/week (worth $300-600 @ $50-100/hour fully-loaded cost) vs $0 free tier cost.

When to upgrade: Upgrade to Business ($12/user) when team reaches 10-15 people and needs shared habits ("No meetings before 10am company-wide") or team buffer policies (15min between all meetings enforced).

SMBs (16-100 people)

Best plan: Business ($12/user/month) Why: Shared habits enforce company-wide calendar policies (e.g., "No meetings Wednesday afternoons = focus time"), buffer policies prevent meeting overload, admin controls for team coordination.

ROI calculation (25-person team):

• Cost: $300/month ($12/user × 25) = $3,600/year
• Time saved: 6 hours/week per person × 25 people = 150 hours/week saved on calendar management
• Value: 150 hours/week × 52 weeks × $50/hour = $390K/year value vs $3.6K cost = 108x ROI

Shared habit examples:

• "No meetings Friday afternoons" (company-wide focus time)
• "No meetings before 10am" (protect morning deep work)
• "Block 2 hours Tuesday/Thursday for project work" (recurring focus blocks)

When to upgrade: Upgrade to Enterprise (custom pricing) when team reaches 100+ users and needs SSO, dedicated support, advanced analytics.

Not Recommended: Large Enterprises (100+ people)

Why not: Reclaim.ai only supports Google Calendar (most Fortune 500 use Microsoft Outlook/Office 365). Google-only requirement excludes 50%+ of enterprise market.

Alternative: Use Motion ($19-34/user with Outlook support) or stick with Microsoft Viva Insights (included in Office 365 E5, basic focus time protection).

Reclaim.ai is the best AI calendar assistant for meeting-heavy teams drowning in calendar Tetris who need to protect 40% of their week for focus time at $0-12/user/month. Habit scheduling automatically defends recurring deep work blocks (e.g., "Block 3 hours Friday morning for strategic planning") and reschedules dynamically when urgent meetings conflict → Saves 8-12 hours/week on calendar management for sales leaders, SDR managers, customer success roles booking 20-50 meetings/week.

Why Reclaim.ai wins: Smart 1:1s eliminate 2-4 hours/week coordinating recurring team check-ins (auto-book when both calendars align vs Slack/Calendly back-and-forth). Buffer time policies prevent back-to-back meeting burnout (enforce 15min breaks before/after all calls). Multi-calendar sync merges work + personal calendars to show true availability (prevents double-booking during dentist appointments). Generous free tier (unlimited habits/tasks/scheduling links) enables testing before team rollout.

The catch: Google Calendar-only (no Microsoft Outlook support excludes 50%+ of enterprise market - use Motion instead). 1-2 week AI learning curve to optimize scheduling patterns (not instant value like Calendly). Hard to quantify ROI (time-saved value subjective vs Calendly's clear conversion metrics). Both participants need Reclaim.ai for smart 1:1s (limits team adoption if counterparts use Outlook/other tools).

Best for: Sales leaders/managers with 20-40 meetings/week needing focus time protection, SDR managers coordinating 5-15 rep weekly 1:1s automatically, customer success booking 30-50 client calls/week requiring buffer time to prevent burnout, RevOps teams juggling multiple projects needing protected deep work blocks.

Not for: Microsoft Outlook/Office 365 users (Reclaim.ai doesn't support - use Motion $19-34/user instead), solopreneurs with <10 meetings/week (simple Calendly/Cal.com sufficient for low meeting volume), teams needing instant ROI proof (Reclaim's time-saved value harder to measure vs Calendly's conversion metrics).

Reclaim.ai saves $300-600/week in time value (6-8 hours @ $50-100/hour fully-loaded cost) for $0-12/user/month = 500-1000x ROI for meeting-heavy roles. The free tier makes it risk-free to test habit scheduling effectiveness before committing budget.

Rating: Silver Medal - Best AI calendar assistant for focus time protection with habit scheduling defending 40% of calendar, smart 1:1 auto-coordination, and buffer time policies at $0-12/user. Saves 8-12 hours/week on calendar management for meeting-heavy roles. Limitation: Google Calendar-only (no Outlook), 1-2 week learning curve, harder ROI justification vs traditional scheduling tools. Not Gold: niche use case vs universal booking needs, Google-only limits TAM, subjective time-saved value vs measurable conversion metrics.