Reclaim

Reclaim is an AI scheduling automation layer that sits on top of Google Calendar or Microsoft Outlook and continuously optimizes the calendar in real time. It does not replace the calendar — it adds a priority-aware AI engine that auto-schedules tasks, habits, focus blocks, smart meetings, and buffer time, and dynamically rearranges them as new conflicts arise. Founded in 2019 and acquired by Dropbox in August 2024, it operates as an independent product under Dropbox ownership. Trusted by 60,000+ companies as of post-acquisition growth.

AI Focus Time: sets weekly deep-work goals, auto-fills blocks, and adapts as meetings are added. AI Habits: flexible recurring routines (lunch, exercise, planning) that flex around hard commitments rather than rigidly repeating. AI Tasks: syncs tasks from connected PM tools and auto-schedules them to calendar in priority/deadline order, breaking longer work into manageable chunks. Smart Meetings and Scheduling Links: priority-aware booking links that surface additional availability over lower-priority reschedulable events — reported to provide 524% more availability vs. static Calendly links. Buffer Time: auto-schedules travel and prep time around meetings. AI Planner and Assistant: chat-based interface to plan, prioritize, and optimize the schedule. Workforce Analytics and Team OOO Calendar: team-level time tracking, capacity insights, no-meeting day policies, and out-of-office visibility. Outlook support launched August 2025 bringing full feature parity for Microsoft-centric workplaces.

AI engine is the core product, not a feature layer — it runs continuous priority-aware scheduling logic using task deadlines, habit preferences, and meeting constraints. AI Planner chat interface and AI Assistant allow natural-language schedule optimization. AI Initiatives enforce org-wide scheduling policies. Zoom integration enables meeting transcript ingestion to auto-generate follow-up action items and recommended time blocks. REST API is publicly available (API key authentication via developer settings). No official first-party MCP server exists as of June 2026; however, multiple community-maintained MCP servers are available on GitHub, PyPI, and npm (e.g., johnjhughes/reclaim-mcp-server, universalamateur/reclaim-mcp-server) that expose 14–40 tools covering tasks, habits, calendar events, focus time, and analytics — all built on Reclaim's public API. Also reachable via Zapier's MCP layer. MCP coverage is community-driven, not officially supported; reliability risk applies.

Four tiers as of 2025–2026 (prices vary slightly across sources; anchored to most frequently cited figures): Lite (free forever, single user, 3-week scheduling range, 3 habits, 1 Smart Meeting, limited integrations); Starter (~$8–$10/user/month, up to 10 seats, 8-week range, unlimited habits, unlimited task integrations with Todoist/Asana/ClickUp/Jira/Linear, 3 scheduling links, people analytics); Business (~$12–$15/user/month, up to 100 seats, 12-week range, unlimited Smart Meetings, CRM event routing, Zoom transcript integration, onboarding workshops); Enterprise (~$18–$22/user/month, 100+ seat minimum, annual only, adds SSO, SCIM provisioning, domain capture, org-wide analytics, dedicated support). Annual billing saves ~29%. 14-day Business trial available at signup. Pricing reportedly unchanged post-Dropbox acquisition.

Native calendar integrations: Google Calendar (full, primary), Microsoft Outlook (launched August 2025, full feature parity). Task/PM integrations: Asana, Todoist, ClickUp, Jira, Linear, Google Tasks (Starter and above). Communication: Slack (status sync, DND, task creation via slash commands, daily agenda digest). Video: Zoom (conferencing links, transcript ingestion on Business+), Google Meet, Microsoft Teams. Webhooks available for embedding scheduling links in external tools including CRMs. Google Workspace Marketplace listing. No native mobile app — web-only with no iOS/Android push notifications. Apple Calendar not supported.

SOC 2 Type II certified as of September 2023, renewed 2024, audited by A-Lign with zero exceptions. GDPR and CCPA compliant. Certified under the EU-US/UK/Swiss Data Privacy Framework. HackerOne penetration test completed 2023 with all critical findings remediated. Infrastructure hosted on AWS (us-east-1 and us-east-2). All data encrypted in transit (HTTPS/TLS) and at rest. Operates on least-privilege model accessing only calendar metadata. Explicit policy: will never sell or share calendar data with third parties for profit or co-marketing. Trust Center at trust.reclaim.ai (powered by SafeBase). SSO and SCIM provisioning on Enterprise tier. Not HIPAA compliant — explicitly flagged as unsuitable for organizations handling PHI.

Founded 2019 in Portland, Oregon by Patrick Lightbody (CEO, serial founder, original Selenium contributor, prior exits in software testing) and Henry Shapiro (Co-founder, former VP of Product and GTM at New Relic). Raised $9.5M across two rounds — seed (May 2021, $4.8M led by Index Ventures and Gradient Ventures) and a Series A (October 2022) — from investors including Index Ventures, Gradient Ventures, Flying Fish, Calendly, Character.vc, Operator Partners, Yummy Ventures, Grafana CEO Raj Dutt, and former GitHub CTO Jason Warner. Acquired by Dropbox (NASDAQ: DBX) on August 20, 2024 for undisclosed terms; full team of 22 joined Dropbox. Product continues operating independently under the Reclaim brand. At acquisition, 320,000+ users across 43,000+ companies including PagerDuty, Zapier, and GitHub. Post-acquisition user base cited at 60,000+ companies.

Moderate. Reclaim is a strong individual productivity and team scheduling tool, but its fit for a firm is functional rather than strategic — it optimizes the calendars of deal team members, analysts, and EAs rather than touching deal data, portfolio tracking, or LP relationships. Most valuable for protecting focus time, automating 1:1 scheduling, and reducing calendar overhead for a lean investment team. The lack of a native mobile app is a real limitation for partners managing schedules on the go. Dropbox ownership provides enterprise stability and infrastructure but introduces some product roadmap uncertainty (deeper Dropbox ecosystem integration may dilute the standalone scheduling focus). MCP access is community-maintained only, which limits clean AI-native workflow integration relative to tools with official MCP servers. Sensitivity is Medium — it reads calendar metadata and task titles but not deal documents, CRM records, or financial data.

No native iOS/Android mobile app — web-only with no push notifications, a persistent top complaint. No official MCP server; community implementations only, with associated reliability and support risks. Not HIPAA compliant. Apple Calendar not supported. Task management is lightweight compared to dedicated tools like Motion — no subtasks, limited hierarchy. Outlook support launched August 2025 with minor API-driven constraints (hashtag handling, scheduling link accuracy). Post-Dropbox acquisition, roadmap increasingly tied to Dropbox ecosystem priorities. Enterprise tier requires 100-seat minimum, making it expensive for small firms. Pricing inconsistently published across sources — verify current rates directly on reclaim.ai/pricing.