Reclaim.ai pricing

About

Reclaim.ai is an AI-powered calendar and scheduling assistant that automatically defends focus time, schedules recurring habits and tasks, optimizes meetings, and syncs across calendars. It plugs into Google Calendar and Outlook and positions its automation as a fleet of “AI Agents” (5 on the free tier, scaling to unlimited on Enterprise) that continuously re-plan a user’s week around shifting priorities.

The product targets individual professionals and teams alike: a free single-user Lite plan serves solo adopters, while the paid Starter and Business tiers are sold per seat to teams (up to 10 and up to 100 seats respectively), and Enterprise covers larger orgs with SSO/SCIM and dedicated onboarding. Reclaim positions itself directly against Clockwise, Motion, and Calendly — it even offers a switching discount for customers migrating off those tools.

Reclaim.ai was acquired by Dropbox in 2024, folding the scheduling assistant into Dropbox’s productivity portfolio while continuing to operate under its own brand and pricing page. That backing is relevant context for its enterprise security posture (SOC 2 Type II, GDPR, DPF) and its continued standalone go-to-market.

Pricing summary : per-seat AI calendar subscription with a free single-user tier

Reclaim.ai uses a per-seat subscription with two pricing dimensions:

1. Seat tier (feature-gated): Four tiers — Lite (Free, single user), Starter ($12/seat/mo monthly or $10/seat/mo annual, up to 10 seats), Business ($18/seat/mo monthly or $15/seat/mo annual, up to 100 seats), and Enterprise ($22/seat/mo, over 100 seats, contact sales). Higher tiers unlock more AI Agents, longer scheduling ranges, more Calendar Syncs/Scheduling Links, and team features.
2. Billing cadence: Monthly or annual, with Reclaim advertising a 29% discount for annual billing (the page’s toggle is labeled “Yearly – SAVE 20%”). A “Save 30% today-only” new-user promo and program discounts (50% students, 20% nonprofit/startup, 20% switcher) layer on top.

What makes this different: The free Lite plan is uncapped for any single user, so Reclaim only begins metering by seat once a team forms — value is gated by seat count and AI-Agent quota rather than by usage volume.

Pricing by product

Reclaim.ai (Individual & small-team plans)

Reclaim.ai (Business & Enterprise plans)

Sales motions across products: PLG / self-serve for Lite, Starter, and Business; sales-led for Enterprise and the team add-ons.

Team add-ons (sales-quoted)

Hidden costs : per-seat math and the annual-billing lock-in

The “$10/seat” headline understates what a real team pays, because Reclaim prices the whole team at one tier and the cheapest rates only apply to a full 12-month upfront commitment. Two real-world examples:

A 12-person team on Business (annual)

Reclaim’s Starter tier caps at 10 seats, so a 12-person team is pushed up to Business — and annual pricing means the full year is billed upfront.

The lesson: crossing the 10-seat Starter cap forces the whole team onto Business, and the advertised $15 rate only holds if you prepay a full year — a month-to-month 12-seat team pays $18/seat ($216/mo) instead.

A 5-person team that wants monthly flexibility

The lesson: monthly billing costs ~20–29% more than annual. The “29% saving” Reclaim advertises is real, but it’s a trade for a year of prepaid lock-in.

Want to estimate your own Reclaim.ai bill? Use the Reclaim.ai pricing calculator to model your monthly cost based on seat count, tier, and billing cadence.

Pricing evolution : from free beta to four-tier per-seat under Dropbox

Reclaim spent its first year and a half free, then built a per-seat ladder that has roughly doubled at the entry point — from ~$6.50 in 2022 to $10–$12 today — while expanding from three tiers to four. The 2024 Dropbox acquisition is the structural inflection: ownership changed hands but the standalone pricing page did not.

Cadence

Tracked range: 2021-03–2026-06. Quarters not listed above were not separately captured; Wayback coverage thins after mid-2023, so 2023 Q3–2026 Q1 price movements are unknown between the 2023-05 snapshot and the 2026 live capture.

Notable changes

• 2021 (full year) — Reclaim runs an uncapped free beta; the pricing page literally advertises “Free through 2021” (Wayback 2021-03-05 / 2021-08-02).
• 2022-04-23 — First paid tiers go live: Free / Pro ($6.50/seat annual) / Team ($9.50/seat annual), establishing the per-seat model (Wayback 2022-04-23 screenshot).
• 2023-05-10 — Page restructures from 3 columns to 4 tiers (Lite / Starter / Business / Enterprise) priced “per user”, Starter near $8 (Wayback 2023-05-10 screenshot).
• 2024-08-20 — Dropbox acquires Reclaim for a reported $40.2M; founders publicly commit to “no planned changes to pricing or customer support anytime soon” (reclaim.ai/blog/dropbox-acquires-reclaim; TechCrunch 2024-08-22).
• 2026-03-27 — Rival Clockwise sunsets and recommends migration to Reclaim; Reclaim offers a 100% price match on the next 12-month term through 2026-06-30 (reclaim.ai/blog/clockwise-vs-reclaim).

The Dropbox acquisition in detail

On 2024-08-20 Dropbox acquired Reclaim.ai — a Portland, Oregon startup founded in 2019 by Henry Shapiro and Patrick Lightbody — for a reported $40.2 million, with all 22 employees joining Dropbox. At the time Reclaim reported more than 43,000 companies and 320,000 users, and team plans started at $8/person/month. The founders’ note and Dropbox’s messaging both emphasized continuity: Reclaim would remain a standalone product with its own roadmap (Outlook support, new assistant features) and its own pricing page. Nearly two years on, that has held — the pricing surface still lives at reclaim.ai/pricing and bills per seat rather than being absorbed into a Dropbox bundle.

What’s unique : free single-user tier, AI-Agent quotas, switching discounts

1. A genuinely uncapped free tier for solo users. Reclaim’s Lite plan is free forever for any single user — not a 14-day trial or a feature-crippled demo. It includes real AI time-blocking, habit scheduling and one calendar sync. Metering only kicks in when a team forms, which makes the value metric “seats in a team” rather than “tasks scheduled”. That’s unusual in productivity SaaS, where the free tier is usually a funnel teaser; here it’s a durable product that defers all revenue to the moment collaboration begins.

2. Automation metered as “AI Agents”, not usage volume. Reclaim brands its scheduling automation as AI Agents and gates them by tier — 5 on Lite, 10 on Starter, 50 on Business, unlimited on Enterprise — alongside scheduling-range limits (1 week → 12 weeks) and calendar-sync counts. The price ladder climbs by capacity and feature unlocks, not by how many calendar events Reclaim re-plans, so a heavy individual user never sees an overage bill. This keeps the bill predictable, but it also means power users on a low tier hit hard caps rather than paying as they grow.

3. Competitive switching discounts baked into the pricing page. Reclaim publishes self-serve discounts for switchers from Clockwise, Motion and Calendly (20% for 6 months), plus a 100% price match for Clockwise migrants through 2026-06-30. Turning competitor churn into a pricing lever — rather than a sales-desk negotiation — is a deliberate land-grab in a consolidating AI-calendar market (see our Clockwise pricing blueprint for the other side of that migration).

Strengths & weaknesses

Billing UX : monthly/annual toggle, seat tiering, program discounts

• Yearly ↔ Monthly toggle — a “Yearly – SAVE 20%” / “Monthly” switch on the pricing page swaps per-seat rates (Starter $12→$10, Business $18→$15); Reclaim’s FAQ quotes a 29% annual saving.
• Seat-tier upgrade path — accounts can upgrade from Starter to Business in-product to unlock additional features; tiers are capped by seat count (10 / 100 / 100+).
• New-user promo banner — a persistent “Save 30% today-only on Starter & Business plans (special new user offer)” banner runs across the pricing page.
• Program discounts — self-service discount programs for students/educators (50% for 12 months), nonprofits (20% for 3 years), startups (20% for 3 years), and switchers from Clockwise/Motion/Calendly (20% for 6 months).
• Payment & assessment controls — all major credit cards accepted; alternative payment methods and security assessments are handled via contact (hello@reclaim.ai / security@reclaim.ai), with some methods requiring a minimum purchase.

Strategic wins : free-tier land-grab, seat metering, switcher capture

1. The free tier deferred monetization to the exact moment value compounds

By keeping Lite uncapped for solo users and only charging once a team forms, Reclaim aligned its price with the moment its product becomes mission-critical — multi-person coordination. The free beta through 2021 built a 320,000-user base before a single dollar was charged, which is a textbook PLG flywheel. For the broader pattern, see our guide on choosing the right usage metric — Reclaim’s metric is “seats in a coordinating team”, not “calendar events scheduled”, which is exactly why solo power users never feel squeezed.

2. Per-seat with feature gates kept the bill predictable as AI costs rose

Reclaim resisted the temptation to meter the AI itself. Where rivals like Motion bolt credit-consumption onto AI features (pushing bills up 20–40%), Reclaim folds its AI Agents into flat per-seat tiers. That predictability is a real buyer advantage in a market where usage-based AI billing can produce bill shock — and it let Reclaim raise the entry price from ~$6.50 to $10–$12 without changing the shape of the bill. It also bucks the broader shift away from per-user licenses that many AI vendors are now riding.

3. Turning competitor shutdowns into a self-serve acquisition channel

Reclaim published switcher discounts (Clockwise/Motion/Calendly) directly on the pricing page and layered a 100% price match for Clockwise migrants when that rival sunset in March 2026. Converting a competitor’s collapse into a one-click pricing incentive — rather than a bespoke sales motion — is a low-cost land-grab that compounds as the AI-calendar category consolidates.

Areas to improve : seat-cap friction, Enterprise opacity, acquisition uncertainty

1. Seat caps create cliff-edge upgrades instead of smooth scaling

The 10-seat Starter ceiling means an 11th hire jolts a team from $10/seat onto Business at $15/seat — a 50% per-seat jump triggered by one person. A fairer fix would be a volume-graduated Starter (e.g., $10 up to 10 seats, then a modest step) or letting teams overflow a few seats at the Business rate without a full plan migration. As it stands, the cap punishes the exact growth Reclaim wants to encourage.

2. Enterprise carries a list price but still hides behind Contact Sales

Listing “$22/seat” on the Enterprise tier sets an anchor, but the actual quote routes through sales — so buyers can’t self-serve the one tier that includes SSO/SCIM. Publishing a transparent floor (even “from $22/seat, 100-seat minimum”) would let mid-market buyers qualify themselves before booking a call, matching the transparency Reclaim already shows on its other three tiers.

3. Post-Dropbox pricing autonomy is an open question

Reclaim’s founders promised “no planned changes to pricing or customer support anytime soon” at acquisition — but “anytime soon” is not “never”. Acquired productivity tools have a history of eventual bundling, price increases, or absorption into the parent’s plans. Reclaim would build trust by publishing an explicit pricing-stability commitment (a “we won’t raise your rate for N months” guarantee) so customers — especially Clockwise migrants signing 12-month terms — can plan with confidence.

Key takeaways

1. Per-seat, four tiers, free for one. Reclaim charges $10–$15/seat (annual) for Starter and Business, $22 contact-sales for Enterprise, and nothing for a single-user Lite plan. The bill is gated by seats, AI-Agent quota and feature unlocks — not by usage volume.
2. Annual prepay is the real discount lever. Monthly billing costs ~20–29% more than annual; the advertised “29% saving” is genuine but buys it with 12 months of upfront commitment.
3. The free tier is a strategy, not a teaser. Reclaim ran a free beta through 2021 and still keeps Lite uncapped for solo users, deferring all revenue to the moment a team forms — a clean PLG flywheel that built 320,000+ users.
4. Dropbox now owns Reclaim, but the pricing page didn’t change. The August 2024 acquisition (~$40.2M) kept Reclaim standalone with its own per-seat tiers; founders pledged no near-term pricing changes, and ~2 years on that has held.
5. Competitor churn is a built-in acquisition channel. Switcher discounts and a 100% Clockwise price match (through 2026-06-30) turn rivals’ shutdowns into self-serve pricing incentives.

UBP implications

1. A durable free single-user tier can outperform a trial when the value metric is collaboration. Reclaim shows that if your product only becomes monetizable when multiple people coordinate, giving solo use away forever builds the base that converts later — the metric does the gating, not a paywall.
2. Feature-gated per-seat insulates buyers from AI-cost volatility. By metering AI Agents as a tier quota rather than per-event consumption, Reclaim keeps bills predictable even as underlying AI costs move — a deliberate contrast to the credit-burn and value-metric traps that can spike a bill 20–40%.
3. Seat caps are a packaging choice with real friction. Hard tier ceilings (10/100 seats) simplify the page but create cliff-edge upgrades; teams designing per-seat ladders should weigh whether graduated overflow pricing would convert better than a forced whole-team migration.

Sources

• Reclaim.ai pricing page (accessed 2026-06-08)
• Reclaim.ai Enterprise page (accessed 2026-06-08)
• Reclaim.ai — “Reclaim is joining Dropbox” (founders’ note) (accessed 2026-06-08)
• Reclaim.ai — Clockwise vs Reclaim / migration & price match (accessed 2026-06-08)
• Wayback Machine snapshots of reclaim.ai/pricing, 2021-03 through 2023-05 (accessed 2026-06-08)

Bottom line

Reclaim.ai is a disciplined per-seat product: free forever for one user, $10–$15/seat (annual) for teams, and a transparent ladder gated by seats and AI-Agent quotas rather than usage spikes. It grew a 320,000-user base on a free beta, doubled its entry price as it matured, and was bought by Dropbox in 2024 without disturbing its standalone pricing — now using competitor shutdowns like Clockwise’s as a built-in acquisition channel. The watch-item is the seat-cap friction and what Dropbox ownership eventually means for price autonomy.

Want to compare Reclaim.ai against other AI-calendar and productivity pricing? Browse the pricing blueprint.

Pricing timeline : Major events on a vertical axis

Each milestone below corresponds to a public pricing change, product launch, or material adjustment. Major events use a filled marker; minor adjustments use a faded one.

Current snapshot captured

Jun 2026

Per-seat tiers captured live: Lite Free, Starter $12/$10, Business $18/$15, Enterprise $22 (contact sales); monthly/annual toggle, 29% annual saving. Clockwise-migration price match active through 2026-06-30.

Acquired by Dropbox (~$40.2M)

Aug 2024

Dropbox acquired Reclaim.ai; founders said there were 'no planned changes to pricing or customer support anytime soon.' At acquisition, team plans started at $8/person/month. Sources: reclaim.ai/blog/dropbox-acquires-reclaim; TechCrunch 2024-08-22.

Restructure to four tiers — Lite / Starter / Business / Enterprise

May 2023

Between 2023-02 and 2023-05 Reclaim moved from a 3-column Free/Pro/Team layout to a four-tier Lite / Starter / Business / Enterprise structure priced 'per user', with Starter near $8/seat/mo. Source: Wayback 2023-05-10 screenshot.

First paid tiers launch — Free / Pro / Team

Apr 2022

Reclaim introduced its first paid plans: Free ($0), Pro (~$6.50/seat/mo annual) and Team (~$9.50/seat/mo annual). Per-seat subscription model established. Source: Wayback 2022-04-23 screenshot.

Free beta — 'Free through 2021', tiers Coming Soon

Mar 2021

Reclaim ran an uncapped free beta. The pricing page showed Basic/Pro/Team columns all labeled 'Free forever' or 'Free through 2021', with Team marked 'Coming Soon'. No paid tier was live. Source: Wayback 2021-03-05.