From fantasy football to HR enterprise buyers

Bilal Aijazi built a freemium SaaS to millions of monthly active users—but struggled to convert free users to paid. Then he discovered that most users would never pay, and the real buyers were hiding in plain sight. In this episode, early-stage B2B SaaS founders will learn the freemium SaaS playbook that took Polly from $8/month to 7-figure ARR.

Bilal breaks down exactly how to identify buyers in a sea of free users. You will learn the "Pain Tolerance" metric that proved demand (80% completion on a 5-step install), how to separate "pollinators" from paying customers, and why attaching to expensive company rituals drives sticky freemium SaaS conversion.

In this episode, Bilal also shares how Slack building a competing feature forced him to diversify to Teams, Zoom, and Google Slides—and why creator-based pricing works better than workspace pricing for horizontal products.

This episode is brought to you by:

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🔑 Key Lessons

• 🚀 Pain tolerance signals demand: 80% of users completed a 5-step manual install—proving massive demand before Slack even had an app store.
• 💰 Freemium SaaS conversion requires separating users from buyers: Most free users picking lunch spots will never pay. The buyers are running company all-hands and sales kickoffs.
• 🔄 Surviving platform risk means diversifying: When Slack built Workflow Builder, Polly expanded to Teams, Zoom, Google Slides, and PowerPoint.
• 🎯 Hook conversations into the product: Every signup triggers an email asking for feedback—these conversations reveal which use cases convert to paid.
• 💡 Creator pricing works for horizontal freemium SaaS: Charge poll creators, not every user. Enterprise tiers shift to monthly active users.

Chapters

• The "Punch in the Face" Reality of Startups
• What Polly Does and Who It Serves
• Scaling to Millions of Monthly Active Users
• The Origin: Messaging Platforms Meet Enterprise
• Launching on Slack Before the App Store Existed
• The First Product: Polls in Slack
• The 5-Step Onboarding Nightmare (That Worked)
• Product Hunt Viral Moment
• Transitioning from Viral Bot to Real Company
• The Freemium SaaS Strategy
• The Fantasy Football Customer: First $8/Month
• Finding Buyers in a Sea of Free Users
• Free-to-Paid Conversion Challenges
• What Goes Behind the Paywall
• Horizontal vs. Vertical Approach
• Building Polly Workflows
• When Slack Built a Competing Feature
• Managing Platform Risk
• Why Technical Founders Must Learn Sales
• Building on Multiple Platforms Today
• Would You Start Horizontal Again?
• Lightning Round

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Resources

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