Thomas Kunjappu spent two years building for just one customer. Then he had to figure out how to sell his SaaS positioning to the rest of the market - without a real website, a sales team, or a category anyone understood.
Learn how Cleary evolved its SaaS positioning three times - from "external internal tools team" to "employee experience platform" to intranet replacement - and why having Square as a big-name logo almost hurt more than it helped in enterprise sales meetings. Thomas shares the services to SaaS transition, category creation lessons, and how referrals outperformed every paid channel.
Cleary crossed $1M ARR, raised $7.5M, and serves companies like DoorDash and Scale. The SaaS positioning breakthrough came when Thomas identified the chief people officer as the primary buyer persona.
Key Lessons
- 🎯 SaaS positioning evolves through customer conversations: Thomas shifted Cleary's positioning three times, simplifying each iteration based on what resonated with buyers in the enterprise sales process.
- 🤝 Pre-meetings transform enterprise sales outcomes: After a disastrous 20-person demo, Thomas learned to hold one-on-one meetings with key stakeholders first so they champion the deal.
- 📉 A big-name logo is not a sales shortcut: Pitching "don't you want to be like Square" backfired because every prospect saw their company as fundamentally different.
- 🏢 Services-first validates before you build SaaS: Cleary worked as a services provider for Square for two years, retaining the IP while validating with real usage.
- 💰 Re-segmenting beats category creation for faster revenue: Thomas realized Cleary was replacing existing intranet and onboarding budgets, not creating net-new spend.
Chapters
- Introduction
- Thomas's favorite quote and the obstacle is the way
- What Cleary does and the employee experience platform
- SaaS positioning challenges and the intranet comparison
- How the idea was born at Twitter
- Landing Square as the first customer
- Enterprise decision-making with three budgets at Square
- Bootstrapping the first two years without fundraising
- Challenges of building a custom solution for one customer
- Forking the codebase and transitioning to SaaS
- Ending the services relationship with Square
- Timeline from customer one to customer ten
- The pandemic's impact on growth
- Enterprise sales lessons and the 20-person room
- Why keeping sales meetings small matters
- Evolving SaaS positioning from services to employee experience
- Category creation vs re-segmenting an existing market
- Growth channels beyond referrals
- The sales process from discovery to close
- Enterprise sales cycle timelines
- What growth channels failed and why
- Lightning round
Resources
