107: The Influence of Creative Marketing Strategy on Customer Motivation

By: Rachael Seda
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In this episode of The Corporate Dropout, we chat with Jen Pressley, the Head of Leesa Sleep. We discuss pivotal moments that shaped Jen’s career path and how embracing change and seizing opportunities propelled her toward success in the e-commerce and digital marketing industries. She dives into creative marketing strategy and its influence on customer motivations.

Jen also shares her perspectives on leadership as a woman in a male-dominated industry, highlighting the importance of empowering other women to break barriers and thrive in their careers. 

In today’s episode, you’ll learn:

  • Jen’s transition from fine arts to a career in business
  • How to harness creativity and design to elevate the customer experience
  • How Jen leads Leesa Sleep’s brand revitalization and strategic partnerships
  • Lessons Jen learned from founding and scaling a clean beauty brand




About Jen Pressley

I’m Jen Pressley, and I lead the Leesa Sleep business, a role I stepped into after our company was acquired last March. Before this, I served as Leesa’s Chief Marketing Officer. At Leesa, we’re not just a mattress company; we’re on a mission to give back. We’ve donated over 40,000 new mattresses to organizations across the US, helping families set up stable homes, supporting young adults who have aged out of foster care, and providing fresh bedding to shelters.

My passion lies in businesses that have a purpose beyond profits. In 2020, I founded Principle Beauty, a clean beauty brand focused on delivering high-performance, naturally-derived makeup in plastic-free packaging. I wanted to offer an alternative to the excessive plastic waste in the personal care industry.

My journey to business leadership wasn’t conventional—I studied fine art! But I’ve learned that embracing change and seizing opportunities are key to success. It’s important for me to be a role model to other women. 




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