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Reclaim AI

AcquiredFreemium🇺🇸Near-Breakeven

Your calendar, finally as smart as your priorities

86

Overall score

35

Heat score

Pricing

Free$0/month
Starter$8/user/month billed annually
Business$12/user/month billed annually
Enterprise$18/user/month billed annually

Technical Specs

Inputs

Calendar Event, Task Title, Deadline, Priority Level, Habit Definition, Meeting Availability, Team Schedule

Outputs

Auto-Scheduled Calendar Block, Focus Time Event, Smart Meeting Invite, Scheduling Link, Habit Time Block, Productivity Analytics Report

AI Type

Agentic AI

Model Architecture

Custom/Proprietary

Daily Prompts

N/A

Context Length

N/A

Output Quality

Accuracy

86%

Content

84%

Reasoning

83%

Company Profile

Company

Reclaim AI, Inc.

Founded

2019

HQ

Portland, Oregon, USA

Employees

25

Total Raised / Total Funding

$9.5M

Revenue

$2.1M

Valuation

$25M

ARR

$2.1M

CEO

Henry Shapiro

Overview

Estimated Paid Users

16K

Current estimate

Total Earnings Till Date

$2.1M

+3.29% from last month

Market Share

1.2%

Current share

Average Session

18

Per active user

Hallucination Rate

14%

Model quality signal

Growth Rate

+1.63%

Monthly active users

Burn Rate

$1.8M

Total expenses / years active

Paid User Gain

+15.15%

Monthly paid user trend

Profit Analysis

$6M

Total Loss

$5.5M

Total Profit

$10.3M

Performance Metrics

Accuracy

86%

Context

84%

Reasoning

83%

Safety

82%

Benchmarks

No benchmark scores available.

Reclaim AI Models

Reclaim AI v3.5 (Dropbox Era)

Type: Other

Description: Current production version of Reclaim AI under Dropbox ownership, featuring full Google Calendar and Microsoft Outlook support, Smart Meetings, AI-driven task scheduling, People Analytics, and integrations with Asana, Jira, ClickUp, Linear, Todoist, Slack, and Zoom.

Architecture: Custom/Proprietary

Reclaim AI v3.0

Type: Other

Description: Introduced Smart Meetings GA and Priority Engine 2.0, which used machine learning to predict meeting skip/reschedule likelihood and proactively reallocate focus time. Served 320,000+ users across 43,000 companies at time of Dropbox acquisition.

Architecture: Custom/Proprietary

Reclaim AI v2.0

Type: Other

Description: Major release introducing Team Habits, Buffer Time, and team-level calendar coordination. Transformed Reclaim from a personal productivity tool into a team scheduling platform, driving 250% YoY growth in enterprise subscriptions.

Architecture: Custom/Proprietary

Funding Rounds & Investors

Total Funding

$9.5M

Rounds

2

Seed

$3.2M

Oct 2022

$3.2M pre-Series A round from new and existing investors including Yummy Ventures, Character.vc, Flying Fish, Operator Partners, Grafana CEO Raj Dutt, and former GitHub CTO Jason Warner; source: BusinessWire 2022-10-27

Seed

$4.8M

May 2021

$4.8M seed round led by Index Ventures with Gradient Ventures co-leading; source: BusinessWire 2021-05-26 and Reclaim blog post

Founders/Team

HS

Henry Shapiro

Co-Founder & CEO

PL

Patrick Lightbody

Co-Founder & CTO

Direct competitors

No direct competitors available.

Change Log / Major Updates

2024 · Apr 23

Launched Smart Meetings as a generally available feature — the first AI tool specifically designed to automate meeting scheduling coordination across entire teams, finding optimal times based on collective availability and priority.

2024 · Aug 20

Dropbox acquired Reclaim.ai for an undisclosed sum. The full team of ~25 employees joined Dropbox, with a commitment to continue product development and support all existing users without pricing changes.

2025 · May 12

Reclaim expanded beyond Google Calendar exclusivity with full Microsoft Outlook Calendar support, dramatically widening the product's addressable enterprise market under Dropbox ownership.

Compliance, Integrations & Support

Industry: Not specified

Compliances: Not specified

Integrations: Google Calendar, Microsoft Outlook, Slack, Zoom, Google Meet, Asana, Jira, ClickUp, Linear, Todoist, Google Tasks, HubSpot, Raycast, Webhooks, Dropbox

Support:email, help center, community forum, enterprise support

Target audience: Knowledge Workers, Product Managers, Software Engineers, Executives, Remote Teams, Freelancers, HR Teams, Sales Teams, Marketing Teams, Engineering Teams

Supported languages: English

Reclaim AI Acquisitions

RA

Reclaim AI, Inc.

August 20, 2024

N/A

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More About Reclaim AI

The Calendar That Actually Knows What Matters

In 2019, two former New Relic colleagues looked at the modern knowledge worker's calendar and saw a broken system. Meetings filled every gap. Deep work happened at 10pm. Lunch breaks were aspirational. Henry Shapiro and Patrick Lightbody founded Reclaim.ai on a simple but radical thesis: the calendar should be intelligent enough to protect what matters, not just record what's been scheduled.

Reclaim operates as an intelligent layer on top of Google Calendar — it doesn't replace your existing tools, it makes them smarter. When you add a task from Asana or Jira, Reclaim finds the best available time to work on it, respects your deadlines and priorities, and automatically reschedules if something urgent displaces it. Habits like lunch, exercise, or a daily review get defended as flexible blocks that yield to more critical events but bounce back when space opens up. The result is a calendar that reflects your actual priorities rather than whoever sent the last meeting invite.

  • Focus Time: AI defends uninterrupted deep-work blocks based on your goals and calendar gaps
  • Smart Meetings: Auto-finds optimal times for 1:1s and group meetings across all attendees' schedules
  • Task Integrations: Bi-directional sync with Asana, Jira, ClickUp, Linear, Todoist, and Google Tasks
  • Scheduling Links: Share AI-powered availability links that respect your priorities and buffer times
  • People Analytics: Team-level visibility into meeting load, focus time, and work-life balance metrics

By August 2024, when Dropbox acquired the Portland startup, Reclaim had grown to over 320,000 users across 43,000 companies — including PagerDuty, Zapier, and GitHub — with roughly $2.1M in annual recurring revenue. Dropbox paid an undisclosed sum for a team of 25 and a product that had quietly become the go-to calendar intelligence layer for engineering and product teams. Under Dropbox ownership, Reclaim expanded to Microsoft Outlook support in 2025, dramatically widening its addressable market.

Reclaim AI FAQ's

Does Reclaim AI work with Microsoft Outlook?

Yes. Following the Dropbox acquisition in August 2024, Reclaim expanded beyond its original Google Calendar-only support and launched Microsoft Outlook integration in 2025, making it available to a much wider range of enterprise users.

What happens to my Reclaim data now that Dropbox owns it?

Reclaim operates as a distinct product under Dropbox ownership. The founding team joined Dropbox and the product continues to be developed independently. Reclaim's privacy policy and SOC 2 Type II compliance remain in effect. Dropbox has stated that pricing and features remain unchanged for existing users.

How is Reclaim different from Calendly or Motion?

Calendly is focused on external meeting booking links. Motion replaces your entire task and calendar system. Reclaim takes a different approach: it sits on top of your existing calendar and task tools, intelligently scheduling deep work, habits, and meetings without requiring you to abandon the tools your team already uses.

Can Reclaim schedule tasks from my project management tool automatically?

Yes. Reclaim integrates with Asana, Jira, ClickUp, Linear, Todoist, and Google Tasks. When tasks are added or updated in these tools, Reclaim automatically finds the best time slot on your calendar to work on them, respecting deadlines and priority levels. Completion status syncs back to the source tool.

What is a 'Habit' in Reclaim?

A Habit is a recurring activity you want to protect time for — like a daily lunch break, a morning workout, or a weekly 1:1 review. Reclaim defends these as flexible blocks that yield to higher-priority meetings but reschedule themselves when space opens up, helping users maintain work-life balance without manually managing every recurrence.