Freemium SaaS: 18 Months to 10 Customers Then Liftoff

Jon Fagg spent 18 months struggling to get 10 paying customers. Then he introduced a freemium SaaS model, and within six months, Skedda had more signups than they had managed in the previous two years combined.

In this episode, Jon reveals how Skedda grew from a side project that three part-time co-founders built across time zones into a bootstrapped 7-figure business with 4,000 paying customers. He explains why the freemium SaaS approach - combined with one focused SEO project - replaced every other channel they tried, including handwritten letters in the mail. The freemium model unlocked free trial conversion at scale.

Skedda replaced confusing pricing tiers with a generous SaaS free tier plus one $49 paid plan. That simplicity, combined with vertical-specific landing pages for SEO, created a freemium SaaS flywheel where word of mouth matched organic search as a growth driver.

Key Lessons

• 🎯 Freemium SaaS creates volume that unlocks word-of-mouth: Skedda's free tier drove signups, usage, and feedback that eventually made word-of-mouth as powerful as SEO - all without paid marketing spend.
• 🔄 Simplify pricing to one freemium SaaS tier plus one paid plan: Skedda replaced confusing alliterative pricing tiers with a generous free plan and a single $49 premium option, making the decision obvious for users.
• 🚀 One SEO project can replace paid marketing entirely: Jon restructured Skedda's site with vertical-specific landing pages in a single focused effort, and organic search became the primary customer acquisition channel for years.
• 📉 18 months of failure does not mean the idea is wrong: Skedda's founders tried handwritten letters and various outreach tactics for 18 months before freemium SaaS and SEO unlocked growth - persistence mattered more than tactics.
• 💰 Bootstrapped freemium SaaS can reach 7-figure ARR without funding: Skedda grew to 4,000 paying customers and multiple seven figures with a team of 15, proving this model can scale without venture capital.

Chapters

• Introduction
• Jon's motivation: building things with interesting people
• What Skedda does: space management software
• Why Skedda exists: flexible scheduling across verticals
• Customer range: from farmers to Harvard and Mercedes-Benz
• Business size: 4,000 paying customers and 7-figure ARR
• Origin story: running a sports facility in Melbourne
• Recruiting an engineer doing his PhD in Germany
• Building the MVP and first product iteration
• 18 months to find the first 10 customers
• Trying handwritten letters and other failed tactics
• Introducing the freemium SaaS model and simplifying pricing
• The SEO project that changed everything
• Why SEO became the biggest growth driver
• What held them back from freemium sooner
• The avalanche effect after launching freemium
• How COVID accelerated enterprise adoption
• In-person founder retreats for strategic decisions
• Lightning Round
• Wrap Up

Resources

• Full show notes: https://saasclub.io/296
• Join 5,000+ SaaS founders: https://saasclub.io/email