The Real Journey to Product-Led Growth: Reflections and Lessons Learned from the Trenches

🚀 When we launched our PLG initiative in 2022, I stepped into the role of Head of PLG with more questions on how to apply PLG to our problem. While plenty of educational content about product-led growth was available, I quickly discovered that finding practical, battle-tested, in-the-trenches stories and advice was not easy.

Also knowing the “concepts” of PLG, when you apply it to your industry, customers, problem, solution, software, and in your organization — that’s going to be challenging.

Today, I want to share the key insights from our journey, hoping they'll help others navigating PLG.

🔍 The Reality Check: PLG Is More Than Just Product

One of our earliest realizations was that making your product "PLG-ready" is only half the equation. We initially thought that simply optimizing our product for self-service would automatically lead to users flooding in and converting. The reality? It's much more nuanced than that.

The true challenge lies in conversion - turning those free users into paying customers. We realized this requires a delicate balance of:

• Providing enough value in the free tier to demonstrate willingness to invest

• Creating advanced premium features that are worth upgrading for

• Understanding your industry-specific needs and audience expectations

• Developing an effective conversion strategy and paywall mechanisms to get hand raisers and PQLs (product-qualified leads)

🏆 Four Critical Success Factors for PLG Implementation

1. Revenue-First Mindset 💰

We are not* building open-source software here. We are building a SaaS, and the “freemium” is a tactic to get people in the door and experience the product first. It's important to recognize it’s about generating sales.

Based on my real-life experience, PLG isn't just an innovation feature, but its operational strategy aimed at building a self-sustaining flywheel:

• Generate revenue from upsells

• Reinvest that revenue into product improvements

• Enhance user experience and self-serve capabilities

• Create viral growth and word-of-mouth marketing

• Repeat and accelerate

If you taken Growth courses on Reforge, a faster flywheel will lead to more upsells, allowing for continued reinvestment in product improvements, ease of use, discovery, and self-serve experiences, which increase the likelihood of growing more upsells.

To get the flywheel going, there will be a lot of blockers in the way. We identified the top blockers and needed to find ways to overcome them, leading us to embrace experimentation. 

2. Embrace Experimental Learning 🧪

Success in PLG requires constant experimentation, iteration, and rapid expectations regarding product experience, marketing, and sales.

You could win the first half of the battle, which is you can eventually get people to visit your website, sign up, and try the product. And you will find out that a percentage of these customers cannot activate… why? What should be our user journey? What should we teach them to set up and onboard first? And those that activate and retain, why don't they buy? Is our premium packing not enticing? Is the pricing too high? Who are the decision-makers? How do we identify this?

So, we did discovery and tested all of this. 

We found success through Superhuman Onboarding calls. The process is a 30-minute call. We give the customer access to the product, and they experience its value. During the call, I ask discovery questions. At the end, I pitch "new" pricing and packaging.

We have 5 - 10 Superhuman onboarding calls every day. These calls provide five to ten opportunities to test pricing, messaging, and the customer segment that will be willing to buy.

While we're offering a freemium product, our ultimate goal is to sell. We focused on understanding what drives champions to influence buying decisions by conducting a "sales" call with our customers.

3. Communication: Transparency gets Buy-In 🗣️

With rapid learning and experimentation cycles, I had to maintain organizational support for our PLG efforts. We focused on:

• Sharing traction, trends, and wins

• Being transparent about losses and things that don't work

• Keeping the entire organization informed about PLG progress

• Building trust through honest reporting of both successes and failures

PLG touches every part of your organization, from engineering to sales, design to customer success. Not all relationships will be easy. Transparent communication around learnings and tractions helps maintain leadership backing and reassures colleagues that they will continue to invest their time supporting the PLG initiative.

A lot of things didn't work out in my favor. A lot of our experiments failed. A lot of our sales pitches failed. Sometimes that might hurt morale. I had to continuously re-align the team and the organization.

4. Personal Well-being: Maintaining Health and Sanity 🧘‍♂️

The PLG journey is long and demanding. We had to do rapid experiments and a lot of failures. We had to constantly communicate those experimentations. Keep up the team morale. Keep building relationships with other departments to get support. Work with the engineering and product team to make a PLG experience as a layer of the platform. And the pressure to hit the PLG sales quota. 

It's not easy, to say the least. 

To avoid burnout and maintain effectiveness:

• Practice regular reflection

• Be patient when you lack data points

• Maintain a healthy work-life balance

I ensured I was healthy and balanced my life through all of this learning journey. 

Read about Life as Head of Product-led Growth… What is the role?

1. Day in life as Head of PLG 🧢

2. Week in Life as Head of PLG 🎓

3. Month in Life as Head of PLG ⛑️

4. Quarter in Life as Head of PLG 🪖

5. Year in Life as Head of PLG 🎩

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Learn more https://www.youtube.com/@GaryYauChan/videos 

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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.