PLG Upsell Learning Flywheel

How we went from $0 to $1XX,000 ARR growth in the first year of PLG Launch with a learning flywheel

Author

Gary Chan
September 19, 2024

From $0 to $1XX,000 ARR: A PLG Upselling Journey 🚀

Upselling doesn't have to be a nightmare—and definitely not in the way you might think. Let me share a personal story that transformed my approach to sales and customer growth.

The Unlikely Sales Journey 📞

Picture this: An engineering student turned cold caller, initially skeptical about sales. That was me—convinced that sales was this sleazy, inefficient process. But something magical happened along the way.

I devoured sales books, explored different approaches, and even interviewed a Sales Engineering role at Cisco (I didn’t get the job because they thought I was "too salesy" 😅). The more I learned, the more I realized my initial perceptions were completely wrong.

The PLG Revolution: Reimagining Upselling 💡

Product-led growth was a game-changer for me. Here's how I flipped the traditional sales script.

I deployed the Superhuman Onboarding Approach

Every customers who signup, we schedule a 30-minute call 📞

That’s how we were able to learn fast and iterate 🔄

The PLG Flywheel

Here’s a breakdown of what a 30min onboarding call look like

💥 5 minutes: Explain why we launched for free and reassure every customer we talk to that others sign-up for the same reason

💥 5 minutes: Share live examples of others who are successful using TrustCloud

💥 15 minutes: We give them access to the platform, and they are onboarded immediately. Instead of talking about the software, they can experience how our platform can work for them

💥 5 minutes: Discuss pricing, explain what each tier offers, our business model, and gather feedback about their experience

This is how we built a learning flywheel.

The Superhuman Onboarding Approach

  • Watching customers test-drive our product (delighted the Engineer in me) 🥹

  • Teaching them how to get the most of our product (empowering the Maker in me) 😊

  • Iterate pitching pricing with crystal-clear value (trigger the Sales Strategist in me) 🤑

This way of selling? It felt effortless. No hard sells, no pushy tactics—just genuine guidance.

Key Insights for Transformative Upselling

  1. Value-First Mindset: Show, don't tell

  2. Customer Success as the Core: Be a guide, not a pusher

  3. Transparent Pricing: Clear tiers that speak for themselves

  4. Continuous Optimization: Test, learn, and scale

The Real Secret? 🔑

Customers appreciate guidance when it's authentic. By leading with value and maintaining a customer-centric approach, upselling becomes a natural conversation.

The Ongoing Challenge

PLG isn't a one-time strategy—it's a continuous journey of:

  • Maintaining confidence

  • Testing pitch strategies

  • Implementing smart paywalls

  • Scaling success systematically

💡 Pro Tip: Every customer interaction is an opportunity to build trust, demonstrate value, and create a self-reinforcing growth ecosystem.

Remember: Great upselling feels less like selling and more like solving. It's about creating meaningful connections that transcend traditional transactional approaches

I write about #PLG and #productledsales daily. Please follow me or subscribe to my newsletter! Cheers!

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