2023 Honorees

Jen Pressley


“Businesses that give back and serve a larger purpose are my passion.”


Tell us about your company and role.

I’m the Chief Marketing Officer for Leesa Sleep, a leading omnichannel mattress brand. Leesa is unique because we have a mission for good that gives back to communities in need. I am also the Founder of Principle Beauty, a sustainably formulated and packaged cosmetics brand.

How would you describe yourself?

I’m a high/low leader. That means I like to be able to provide overall goals and vision while also rolling up my sleeves to write copy or work out granular details of a marketing campaign when needed. I believe it’s important as a leader to know the executional details of every marketing channel you plan to invest in. There’s nothing worse than a detached leader who doesn’t understand the mechanics of marketing but is asking their team to do things that don’t make sense. I also like the walls of hierarchy broken down a bit so that everyone feels their most comfortable self and can express their opinions openly. Comfortable, happy people are also high performers. We have an amazing team at Leesa. I’m also a little quirky at times and like to keep the humor flowing, especially in stressful situations. I can talk for hours about food!

What qualities do you think an effective marketer needs to have?

A good marketer should have a deep understanding of their product category and the customer journey (and pain points) in that category. That means talking to customers, working in CX for a few days, immersing yourself in every competitor, and being obsessed with seasonal and economic trends. It’s also important to stay curious and strive to learn more outside of the marketing channels you’re used to. Look for green space. Good marketers also understand the current goals of the business and align campaign and channel targets appropriately. Follow through and campaign hygiene is so important too. These are things that can’t be taught and are critical. The last thing you want is a big talker who calls themselves a “growth hacker” but doesn’t follow through or know how to execute well.  

What has been your biggest professional success so far?

The last few years have been a career highlight. I’ve made the unusual switch from a brand/creative person to a fully immersed marketing leader. It’s been amazing. Understanding what motivates customers and having the ability to inspire action in marketing channels was always my goal in the past and now I’m closer to the process. I’ve also been extremely lucky to be involved in businesses that do more than focus on the bottom line. Businesses that give back and serve a larger purpose are my passion.

Pattern art Pattern art

What causes are you most passionate about?

Sustainability, inclusion, and human rights. Those are broad, but I believe if we get these three things right, the world will be a better place for everyone. There’s clearly a lot of work to do.

What do you think is the biggest challenge facing eCommerce brands?

We are all challenged now with oversaturation in certain channels and the cost of competing in those channels. It’s especially challenging for “disruptor” brands in categories that have peaked and are now waning. Green spaces are harder and harder to find. The winners will be those who spot the trends and pivot to a smarter model or consolidate their efforts before everyone else does.

What's your favorite loyalty program or subscription offering from an eCommerce brand?

The holy grail here is Amazon Prime. That brings real value to customers because they are a marketplace, the biggest marketplace. Costco is another example, again a marketplace, where a subscription (or membership) nets real value everyday. The same goes for credit card loyalty. Those pay off. For independent brands selling one product or category, making subscriptions work is hard and it’s not a great customer experience. The horror stories of being locked into a subscription and not able to cancel are ubiquitous and that’s not good for brand reputation. I’m thinking skincare, personal care products. I never want to push products that don’t improve people’s lives. Make it easy to try your product and be so good at what you do that customers keep coming back for more. That’s when offering a subscription makes sense. 

What do you geek out over?

Professionally: affiliate marketing, AI; Personally: food, travel