Inspiring Women: Jen Pressley Head of Leesa Sleep
A story on the love of handicraft that inspires art, and sleep.
What drew you to joining Leesa and what are you most proud of in your time there?
“ I’m most proud of the care and attention we bring to product quality and to our communities. I’ve grown the business with the launch of more mattresses for a wider range of customer needs, and doubled down on Leesa’s commitment to giving back with our donations to organizations across the US.”
Joining Leesa was the culmination of a history in the creative, non-profit, and interestingly, the mattress space. While I was Creative Director at Suka in NY in 2010, I had the opportunity to meet potential clients in the fledgling DTC mattress space. I was asked to create a brand name, look, and an overall voice and identity for a mattress with the concept of selling mattresses directly to customers, instead of through stores. This was a new idea back then. So, I created a name, full identity, and website framework for the brand — it is now a highly successful mattress brand, Saatva. What drew me to working in the space was an alignment with the owners — a big cornerstone of the brand was treating people exceptionally well, not just selling products. That resonated with me. I eventually joined Saatva full time to lead and grow the content and brand team from 1 person to 12. I named and launched 5 more products and helped grow Saatva into the business it is today. A true startup to success story. During my time at Saatva, we kept tabs on competitors, and I remember being blown away by a newly launched brand called Leesa. What knocked my socks off was Leesa’s community giving and work to help the unhoused. I spotted an Instagram takeover where Leesa sponsored a barber giving free haircuts to folks living on the street. That was a pivotal moment for me. I remember saying to myself “That’s where I want to be.” I don’t think I would have believed anyone at the time if you told me in 8 years I’d be running Leesa.
Since joining Leesa as CMO in 2022, transitioning Leesa through its sale to 3Z in 2023, and now running the Leesa business, I’m most proud of the care and attention we bring to product quality and to our communities. I’ve grown the business with the launch of more mattresses for a wider range of customer needs, and doubled down on Leesa’s commitment to giving back with our donations to organizations across the US. We also launched a closer co-branded partnership with
West Elm with the Leesa x West Elm Natural mattress. This partnership highlights our shared values in creating more meaningful products. I also knew I wanted Leesa to focus on more sustainable practices and launched our CleanHub sponsorship — we sponsor ocean cleanup through CleanHub who works with Green Worms in Kerala that cleans up ocean-bound waste, but also provides financial stability for women in the area. I am also fortunate to be surrounded by an exceptional team of caring and talented people — you can see the output of that care in everything we do.
Journeys aren’t linear, and I’m so curious to learn about your career from founding a plastic-free cosmetic brand to joining Leesa?
I left Saatva in late 2019, after being immersed in the online mattress space for 8 years. I knew I wanted to branch out into a different industry and do something on my own. I was also living a life that was more curated and minimal, and trying my hand at low-waste, plastic free living. I wanted a break from “stuff” and the over consumption that seemed to have bled into every corner of our lives. During that time, I was dismayed at how many cosmetics relied on plastic packing for everything. I wondered, where did this stuff go once someone was done with it? The answer wasn’t a good one. I started researching companies that didn’t rely on plastic packaging and didn’t find much. I also noticed a swelling movement of people and stores catering to our more conscious and minimal lifestyle. I decided I wanted to create something that didn’t exist — a fully compostable, but chic, package — and a formula that didn’t compromise efficacy for ethics. That journey was a year and half of creating a supply chain that didn’t exist and a formula that didn’t exist. I worked with talented people across the globe and launched Principle Beauty, creating the first eye palette in a
fully plastic-free compostable cork and paper package. We did this while the pandemic was actively happening, so the hurdles were big and the lessons even bigger. We had nice momentum with zero-waste stores in the US, and a minimal living chain in Japan. Once I started working with Leesa, I made the decision to wind down that business.
“Before learning about Leesa, I had no idea a mattress specifically designed for larger bodies existed. I especailly appreciate Leesa’s initiatives to launch more mattresses for a wider range of customer needs. ”
So now, how does art play a role in your personal life?
Jen’s artwork and her adorable puppy in her New York home.
I went to Cooper Union where I studied painting and drawing. I always knew I wanted to be making things in my life. That’s how I found myself on the path to creative direction, as the digital age unfolded, to make a living. But I found that working for businesses and “creating” in that sense has a very different purpose than creating art for its own sake. So, I return to making things in my personal life over the course of my working career. I was part of a bespoke collective of makers creating one-of-a-kind handbags in the early 2000s that led me to working with an Italian company out of Florence, and a company in NYC in the early 2000s. This came out of a love for handicraft. I also regularly kept sketchbooks that I would revisit from time to time. I maintain an annual membership to the Met here in NYC or go to see independent shows like Sonya Delaunay’s work. I make a point to seek out epic works whenever I travel: last year to marvel at Gaudi in Spain, a bucket list visit to the Louvre, and an upcoming trip to Vienna to see original Klimt’s at Belvedere Palace.
During the pandemic, I started creating a drawing a day. It culminated in eventually translating those ideas to larger works, going on a week-long artist residency in 2021 to create 3 pieces. Here is some of that work: Art and travel is a focal point of my life, and I keep work in my home that has meaning, makes me happy or reminds me of a place and time associated with freedom and happiness.
“I like to feel a connective pull to art and objects. Work or artifacts that evoke a feeling of longing: jogging a memory, ties to moments in human history, or work that speaks to a time and place of inspiration, where being free to enjoy the world and space for thought are always available.”
Jen Pressley
Jen Pressley is a dynamic leader passionate about mission-driven businesses. In her role as the head of Leesa Sleep, she is dedicated to creating products that improve people’s lives through better sleep. Prior to Leesa, Jen founded a sustainable plastic-free cosmetic brand, and has cumulative decades of experience creating and running brands in the sleep space, non-prots, and higher education. Recently, she launched Leesa’s expanded mattress line to better serve diverse customer needs, while scaling the brand’s commitment to giving back. Since its start in 2015, Leesa has donated over 41,000 mattresses to vital organizations across the U.S. that support unhoused individuals and displaced families. Jen also launched Leesa’s partnership with CleanHub to sponsor the safe collection and recovery of ocean-bound plastic, while creating sustainable jobs. Jen’s unique journey from art and design to entrepreneurship showcases her curiosity, adaptability, and strong business acumen. She advocates for improved customer experiences and social responsibility, connecting with audiences through her passion for great design and human connectivity on the path to better living. Outside of work, Jen enjoys traveling with her daughter, exploring cultures around the world through food and meaningful experiences.