An Operator’s Playbook for Monetizing Product-Led Growth

What do you do when everyone loves your product but no one’s paying for it? That was the challenge facing Beautiful.ai. Founder Mitch Grasso nailed the product, but to build a sustainable business, he brought in operator Jason Lapp as CEO.

In this conversation, Jason shares how Beautiful.ai killed its freemium tier, introduced a credit-card-gated trial without losing momentum, and learned to serve both self-serve and enterprise customers at the same time. He also explains how to listen to customer feedback without becoming a feature factory, and why non-technical founders shouldn’t try to know everything about the tech stack.

If you’re a founder wondering when to put up a paywall — or how to balance PLG with enterprise sales — here's a playbook.

RUNTIME 46:20 EPISODE BREAKDOWN

(3:35) “ The timing of us coming together was really fortuitous for beautiful because he had already built the first version of beautiful and put it in market.”

(6:28) “ Microsoft and Google report that there's close to a billion people that use presentation software on a monthly basis.”

(10:51) “ At a certain point after getting in market, you start to get a different set of signal.”

(14:52) The free trial period is a great opportunity to learn about what customers value most.

(19:56) Leverage “emotional” feedback to improve the customer experience.

(23:46) “ We do have a guiding principle, which is: on the customer side, we generally don't build for one customer need.”

(26:17) Beautiful.ai uses NPS surveys to gather feedback from enterprise and individual users.

(28:49) Since pivoting to paid, they have separate teams for enterprise and individual customers.

(23:02) “ We think about an ICP, and then we think about an IECP, meaning the enterprise as a whole.”

(33:57) Capturing behavioral and attitudinal data to understand customer behavior.

(37:18)  How the broader rise of generative AI has influenced GTM strategy.

(42:33) Jason shares some advice for non-technical CEOs.

LINKS

• Jason Lapp
• Beautiful.ai
• AI Isn’t Coming For Jobs, It’s Coming For Inefficiency
• Continuous Discovery Habits: Discover Products that Create Customer Value and Business Value, Teresa Torres
• Everything You Need to Know About Freemium Pricing, Kyle Poyar, OpenView Partners

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Thanks for listening!

– Walter.