How to Drive Free Users to Monotisable Users?

Today’s episode is with Giancarlo 'GC' Lionetti, the former CMO of Confluent and VP of Self-Serve Growth at Dropbox. (GC also previously spent 6 years at Atlassian, as a sales engineer and product marketing manager for developer tools.)

He describes his career as more of a maze than a ladder, and this functional diversity combined with his deep experience at standout B2B companies gives him a unique perspective. In today’s conversation, we dig deep into why he advocates for a hybrid go-to-market strategy that brings together more traditional selling with modern product-led growth.

We start by mining lessons from GC’s time at Atlassian and Dropbox, including his takes on the differences between their business models and what it takes to make a multi-product go-to-market motion work.

Then we dive right into his advice for a hybrid approach, covering everything from his litmus tests for picking the right metrics, to the structure of his weekly meetings. GC explains how he sinks tons of time into understanding the customer journey, mapping out the delta between reality and the ideal vision. 

He also shares plenty of pro-tips about pricing, packaging, and activation, as well as a broader diagnostic framework that he’s developed to evaluate a company’s go-to-market strategy. We wrap up by focusing on team building for a hybrid go-to-market strategy — from hiring profiles to team structure.

It’s a great listen for founders, product and go-to-market leaders, with tons of examples of specific impactful experiments he ran, metrics that did or didn’t work out, and common traps that he sees teams falling into. 

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