Humanizing B2B Marketing with Humor with Melissa Rosenthal

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Today’s guest is a forward-thinking, inspiring, and exceptional leader. She was named to Forbes’ 30 Under 30, Business Insider’s 30 Most Creative People Under 30, and one of Digiday’s “Changemakers”.

She formerly led marketing as Executive Vice President at Cheddar and VP of Global Creative at BuzzFeed. She was instrumental in helping her last company grow from 0 to 6 Million Users in 5 Years.

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Since recording with Chris, Melissa Rosenthal has moved on from her role as Chief Creative Officer at ClickUp and started a new role as Chief Marketing Officer at Insight Timer.

Melissa and Host Chris Mechanic discuss how to strategically use humor in B2B product marketing, the key components of Product-Led Growth, and the importance of implementing user feedback. 


  1. The key to creating ads that are both funny and effective is making them address the actual problems faced by users in a humorous and relatable way to drive the narrative and enhance its appeal. Speak to existing conversations happening around the needs and struggles of your target customers. Make sure to understand how they feel about the problem and the language they use to describe the problem. Digital communities, on sites like Reddit, can be amazing sources to help you the nuances of your customer.
  2. Great campaigns balance communicating product value with humor in an ad. This makes it feel less like an ad and can be less offputting to customers. With the right tone, B2B marketing can resonate deeply and stay memorable.
  3. It’s essential to gauge the reception of an ad before fully launching it, especially when it hinges on humor. Use a tool for user testing to assess the potential reception and measure whether it will be well-received.
  4. Leveraging the power of PLG (Product-Led Growth) has been one of the major driving forces towards ClickUp’s success. Any amount spent on marketing campaigns would go to waste if the product itself wasn’t fundamentally strong and helpful to users.
  5. Examine all of the interaction points in the customer journey and even though attributing the main source of conversion might be tough, all touchpoints have an essential role and need to be understood.
  6. Providing users with easy-to-access and easy-to-implement templates is a simple way to supercharge your PLG motion and increase conversions from demos. Templates are a great way to onboard users quickly and efficiently, helping them rapidly grasp key product features.

Quote of the Show:

  • “I’ve always led with a contrarian view in everything that I’ve done.” – Melissa Rosenthal



  • Alex Hormozi
  • How Brands Grow by Byron Sharp
  • Grit by Angela Duckworth
  • The Surrender Experiment by Michael Alan Singer
  • Anthony Kennada

Ways to Tune In:

Melissa Rosenthal

Melissa RosenthalCMO, Insight Timer

Chris Mechanic

Chris MechanicCEO & Co-Founder

Podcasts Info:
Creative + UX

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