PLG company: MailMaestro

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

Company and Product

MailMaestro – AI Email Assistant

Founded: 2023, with headquarters in Singapore and New York

Team: 11–50 employees

2025: Trusted by 55,000+ teams worldwide, including MIT, Major League Baseball, and HP

Acquired Flowrite (2024)

Competitors: Superhuman, Fyxer, Otter.ai

Industry/Category

AI productivity software / Email management / Meeting Recorders

Target User Persona

• Primary: Professionals and teams overwhelmed by email volume, looking to save time and improve communication quality

• Secondary: Customer support, sales, marketing, and executives needing fast, secure, and multilingual email workflows like drafting, summarization, and workflow automation

PLG Model Used

Freemium Bottoms-Up with Viral Team Expansion

• Free tier: Basic AI email drafting, summarization, and meeting recorders

• Paid tiers:

  • Professional: For individuals seeking advanced AI workflows

  • Team: Shared Templates, Dashboard, MS Teams integrations

  • Enterprise: Advanced security, compliance, onboarding, and support

• Bottom-up adoption: Individual users start, then invite teams as value compounds

Time to Value (TTV)

• Immediate (minutes):

  • Connect email account or MS Teams

  • Add the Chrome extensions to inject the side panel and the magic compose button

  • AI drafts, summarizes, and improves emails instantly after setup

  • Users see value after their first email or thread summary or meeting recorded and summarized

Onboarding Experience

• Quick install with Gmail and Outlook

• No software to install for web clients; browser extension for added features

• Contextual tooltips and “magic templates” for rapid onboarding

• Progressive feature discovery as users explore more advanced workflows

Key Growth Loops/Virality

• Viral Sharing: Users send AI-enhanced emails with MailMaestro watermark

• Team Recording Loop: Teams adopt for shared productivity gains and meeting summaries

• Word of Mouth: Positive reviews and testimonials drive organic growth

Learn more about Word of Mouth and PLG

PLG Compounding Strategy

Every user gets value fast by installing MailMaestro and sending their first AI-written or summarized email. It only takes a few minutes to start seeing benefits. The onboarding is smooth and easy to follow, and this creates fast activation.

When users send these improved emails and meeting notes, the recipients get a MailMaestro watermark, which increases virality.

People invite their teammates to work together using shared templates and collaboration features. Team collaboration loops make the product sticky for the company.

Being featured on Google Marketplace, leveraging strong word of mouth, and gaining tremendous SEO traffic for their blog.

With every new email, meeting summary, and teammate added, MailMaestro becomes more useful and ingrained in daily workflows. Over time, organizations grow reliant on its AI-powered features, making MailMaestro sticky, hard to replace, and the go-to tool for smarter email and meeting management.

Learn more about SEO and PLG

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- Monday: spotlight a lesser-known PLG company
- 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.