163: Ambushing Goliath (The True Art of Challenger Branding)

If you’re a fan of renegade thinking, then you’ll probably be a fan of David Thompson, CMO of Freshworks, and serial bold marketer. His marketing has historically been fairly subversive, think responding to competitions’ hiring of Cindy Crawford with a RuPaul-led Superbowl commercial (in the early aughts). Or hiring a blimp with “#FailsForce” written on it to circle Salesforce Tower, the tallest building in San Francisco, and home of Freshworks competitor Salesforce.

When asked about being afraid of backlash to his marketing, Thompson responded that, if you aren’t a little afraid of your marketing, it’s probably not worth putting out into the world. He likes to partially gauge this by seeing how his CEO reacts to the pitch—if the CEO immediately mentions that the board will need to take a look, you’re on the right track. Learn more about bold, tactical marketing, rapid rebrands, bartending for Meryl Streep before a performance (her go-to before performing is whiskey), and more on this episode of Renegade Thinkers Unite.