PLG Company: Reclaim.ai

How a Dropbox acquired AI-powered calendar tool, uses product-led growth (PLG) with instant scheduling, deep team integrations, and adaptive automation to serve over 550,000 users across 65,000+ companies.

Author

Gary Chan
September 16, 2025

Every week, I will feature a PLG company and break down how they win.

Company and Product

Reclaim.ai – AI Calendar

Founded: 2019 by Henry Shapiro and co-founders, headquartered in Portland, Oregon

Team: 11–50 employees

Funding: $6.3M raised, $25M valuation as of 2024 (Index Ventures, other notable investors). Acquired by Dropbox on July 2024 for $40.2 million.

Revenue & Users: $2.1M ARR in 2024, 16K customers (historically), now trusted by 550,000+ users across 65,000+ companies

Competitors: Motion, Clockwise

“We don't train AI on your data.” Reassure your customers that they're not the product, and that the AI features will not jeopardize their privacy.

Gary Yau Chan

Industry/Category

Consumer Productivity / AI Scheduling

Target User Persona

Primary: Busy professionals, managers, and knowledge workers seeking to protect time for important tasks, meetings, and personal routines

Secondary: Remote, distributed, and cross-functional teams optimizing meeting scheduling, project work, and habits

Specific: Anyone overwhelmed by calendars, meetings, and shifting priorities looking to improve productivity in their life

No catch free plan guarantee

Read my post on selling PLG / Freemium to a skeptical market:

Product-Led Growth: Launching a Freemium B2B SaaS

How product-led growth strategy drives signups, rapid feedback, and user conversion, even in skeptical, sales-led markets. Learn step-by-step tactics to launch a PLG motion, overcome internal resistance, and leverage onboarding and customer insights to accelerate SaaS growth.

growthwithgary.com/p/launching-freemium-saas

You have to make sure to reassure your customer. Sometimes they just don't believe "free." To them, if it's free, then they are the product. In this case, it is simply a go-to-market strategy.

So reassure your users. Explain why it is free and how it all works.

Gary Yau Chan

PLG Model Used

Freemium + Bottom-Up Team Expansion

  • Free Forever tier: Core AI scheduling, habit tracking, and calendar sync across one account

  • Paid tiers: Unlock multi-calendars, collaboration, analytics, support for teams and enterprises

  • Self-serve onboarding, instant “import calendar” workflows, with nudging users to invite team and set up integrations

"Free" is just a Trojan horse to get users to invite their teammates and ultimately convert them to a business account with a business pricing plan.

Gary Yau Chan

Time to Value (TTV)

Immediate (minutes):

  • Connect Google or Outlook Calendar, and instantly see prioritized focus time, habits, and meetings scheduled automatically

  • Sync multiple task and project management tools and then detect conflicts and recommend adjustments

  • Advanced features like Smart Buffer and Focus Times protect user’s time

Onboarding Experience

  • Setup calendar sync, scheduling links, and priority/habit setup

  • Personalize based on working hours, meeting load, and task urgency

  • In-app bumpers for setting “defensive” schedules, time tracking, and habit planning

  • API integrations, docs, and support for enterprise rollout

Check out Product Led Growth Bumpers to build feature discovery and guidance:

Product Led Growth Bumper: Turn your SaaS into a Growth Engine

PLG bumpers guide free users throughout the product journey, helping them activate, retain, and upgrade into paid customers.

growthwithgary.com/p/product-led-growth-bumper

App integrations

Key Growth Loops / Virality

  • Team Workflow Loop: Teams are invited for automated scheduling, syncing, priority alignment, and more efficient collaboration across meetings and projects

  • Deep Integration Loop: Reclaim gets “sticky” as users connect more calendars, tasks, and channels (Slack, Jira, Zoom, Asana, etc.), making it a center for action

  • Habit Automation Loop: As more users automate habits and routines, they share time management wins with colleagues, driving word-of-mouth

  • Focus and Buffer Time Loop: Visual improvements in personal and team productivity encourage users to invite others

Read more about SaaS Internal Virality and getting the team to use:

SaaS Product Virality using Product-Led Growth

How to create internal virality bottom-up from selling to one individual user then upselling the whole customer's organization. And learn how to create external virality that compounds and drives growth.

growthwithgary.com/p/saas-virality

PLG Compounding Strategy

Users get immediate value by automatically seeing their calendar, meetings, tasks, and habits all re-sorted by an AI. This creates a "wow" effect.

The user is then invited to connect with more integrations and invite their coworkers, followed by nudges encouraging them to realize, "Hey, this is actually going to be more productive for you."

However, it's all part of a go-to-market strategy aimed at getting your business to buy the team account and increase team usage, so you can be asked to upgrade to the higher pay tier. Stickier integrations and increased team usage feed into the bottoms-up PLG distribution.

Read about other PLG Company Highlights:

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- Tuesday: my PLG experience
- Wednesday: Memes on product, AI, and marketing
- Thursday: tactical growth tips
- Friday: raw accounts of my startup journey

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I am Gary Yau Chan. 3x Head of Growth. Product Growth specialist. 26x hackathon winner. Building ClarityInbox. I write about #PLG and #BuildInPublic. Please follow me on LinkedIn, or read about what you can hire me for on my Notion page.