Meet the Founder: Charlotte Lilley of The Retreat Co

Charlotte Lilley is the founder of The Retreat Co, a women-led company creating immersive, year-round experiences that combine adventure, connection, and community. From her early days skiing in the California foothills to a career in tech, Charlotte recognized how transformative shared experiences in the outdoors can be—especially for women seeking confidence, camaraderie, and a sense of belonging. In this Q&A, she shares the story behind The Retreat Co, the moments that make her retreats truly impactful, and her vision for building a year-round community where women feel empowered to explore, connect, and thrive.

 

What inspired you to start The Retreat Co, and what personal experiences shaped your “why”?

I grew up skiing in the California foothills which instilled a love of the whole experience of skiing (maybe except for cold toes). After college I started skiing a lot more and traveling for skiing. Traveling for skiing brought a whole new love of the experience for me. Any excuse to travel, right? I spent 15+ years in startups in the tech industry and I was always planning ski trips in my spare time - friend trips and annual trips at each company I worked at. After years in tech, leading teams, running programs, and planning ski trips on the side, I realized that so many women around me wanted community, adventure, and confidence, but didn’t always feel comfortable accessing those spaces alone. So, in 2018 I started The Ski Retreat because I wanted women to have the same experiences that shaped me: getting outside, trying something new, and realizing they're capable of so much more than they think. Plus, I love a girl’s ski weekend! Fast forward to 2024, I left my tech job to pursue this dream full-time. What was The Ski Retreat is now The Retreat Co where we run year-round experiences for women from skiing, camping and work (corporate) retreats!

Was there a moment when you realized these retreats were truly needed?

On my very first retreat, a woman said, “I’ve skied for years but I’ve never had other women to ski with.” Then another said she’d been nervous to try skiing because her partner always taught her and she never felt confident.  I remember thinking, “oh this isn’t just some fun idea, it’s bringing real meaning to women’s lives. Every season since, more women echo the same thing: they want connection, they want adventure, and they want to do it with other women.

How would you describe the community and connection that forms at your retreats?

It’s instant and it’s real. Women arrive as strangers and by the end of the weekend you’d think they’ve known each other for years. There’s something about being in nature, laughing on the chairlift, celebrating the small wins, and sharing stories over dinner that accelerates connection in a beautiful way. It feels like a girls' sleepover or summer camp for grown women, but with good food, unique activities and everything planned and curated just for you. 

 

What do you think makes the friendships forged at The Retreat Co so deep and long lasting?

Similar to what we were just saying, it’s hard to find other women to do the things you love with for various reasons; therefore 99% of our attendees come solo! I think that lends itself to people just showing up as themselves. There’s no competition, no need to impress, no pressure to be “good enough.” The experience creates space for women to be vulnerable but also playful which is a unique experience that helps form the connection. 

Also, when you genuinely love something (i.e. skiing, being outside, adventuring) and you find other women who love it too, that’s the magic sauce. That shared passion creates an automatic authentic connection. It’s true magic! And even if you’re brand new to the sport or situation, the fact that you were curious enough to try it or to travel across the country for it means you’re already invested at a certain level. 

What sets a Retreat Co experience apart from other women’s outdoor or wellness retreats?

Our slogan “Can’t Sit Still” means that the guests get a lot of value out of the time we have together. We believe women are dynamic so aside from the anchor event (i.e. skiing, camping) we squeeze in a lot of thoughtful experiences that hit a variety of interests, such as an art class, a female entrepreneur guest speaker, yoga, a private chef, and other surprises that we fit into each trip. These are all experiences that many women will never do or plan for themselves. It’s a total blend of adventure, connection, confidence-building and growth—not just wellness or just outdoor skills. It really does feel like a girlfriend's weekend trip. 

Better yet, everything is not just planned for you, but highly curated with intention. Every element from our partners, female founder fireside chats, the yoga, fun welcome bags, beautiful meals and surprises that we design allows women to feel both rejuvenated and deeply cared for. It’s immersive and fun, but also transformative in a variety of ways that women have shared with me. Women leave feeling proud, supported, and more connected to themselves but also to other women. 

I would be remiss not to mention our partnerships, which make the experience that much more meaningful, dynamic, and fun. We intentionally collaborate with women-led and outdoor-aligned brands whose values align with ours (like Wild Rye!). These partnerships show up in the welcome bags, unique activations, and guest speakers. These amazing brands add another level of richness to the experience as the guests get to experience and be a part of an even wider ecosystem of women doing incredible things across different industries.

Can you share a moment from a past retreat that captures the transformation or energy you hope attendees feel?

Oh my gosh there have been so many but one of my favorites is from our Sun Valley World Cup Finals retreat last season. A woman in her early 70s told me she was nervous to join because she thought she’d be the oldest participant and wouldn’t keep up. On day two, she was leading her group down the mountain, laughing, and later said, “I haven’t felt this alive in years.” To boot, she was such a bright beam of good vibes the whole trip. That’s the energy I hope every woman walks away with—that reminder that adventure doesn’t have an age limit and community is for everyone.

What are the most common things women are seeking when they come to one of your retreats?

The reason I hear the most is wanting connection with other women doing something they love. I mean, I hear this multiple times a day. I just went into my messages today and here’s one “I haven’t, but am needing some connection with other women who do similar activities as me. I love to ski, so I’m looking for some “me” time to connect.” The other reasons are connection, confidence, and a break from their everyday routines by joining a supportive and fun environment where they don’t have to plan a single detail once they arrive.

How do you design an environment where people feel supported, safe, and empowered to be themselves?

I’m super intentional about everything. I do not take lightly the fact that women are traveling sometimes across the country, taking time out from work, their family or other life things to be with me. Plus, they've invested financially. I aim to make every detail from the pre-trip Zoom calls to the WhatsApp groups to the way we set expectations on day one. Each day has intentional energy and a flow. We celebrate learning, we normalize being “new” at things, we share stories with each other.  Despite our slogan “Can’t sit still” we build in moments of rest and reflection. And as a host, I really aim to set the tone: warm, approachable, inclusive, and rooted in the belief that everyone belongs here.

Wild Rye is deeply rooted in confidence-building, connection, and showing up as your full self outdoors—how does that mission resonate with the work you’re doing at The Retreat Co?

At The Retreat Co, our whole approach centers on helping women feel grounded, capable, and completely themselves in the outdoors. I believe that when women gain confidence in the outdoors, that confidence translates and shows up in their careers, relationships, and everyday decisions.

Whether someone is trying skiing for the first time or has been shredding it up their whole lives, we focus on building confidence through compassion, shared experience and a focus on connection and fun. The connection piece is huge for us which is why we curate the other fun activities, so that women have different things to bond over. We want every woman to know that she belongs on our trips, she belongs outside and she just fucking belongs. 

So our missions are very aligned! The confidence that women gain on the mountain or trail at Wild Rye is the same confidence we hope they take home from our retreats.

What’s your vision for the future of The Retreat Co, and how do you hope it continues impacting the women who join?

My vision is to keep expanding the ways women can connect with more destinations, more community events, more camp retreats, more corporate retreats, and hot off the press! a physical retreat property. You’re one of the first to hear that I’m in the process of buying a property near Lake Tahoe to create a year-round home for our retreats and gatherings.

Last year was a major growth year for. We rebranded from The Ski Retreat to The Retreat Co with a new logo, website, and name, we added Camp Retreats and Work Retreats, and we expanded our ski destinations. Now the focus is deepening those pillars and filling the “white space” between them.

Connection shouldn’t only happen once a year, so I’m building more touchpoints like seasonal events, virtual retreats, and online workshops to keep that sense of community, confidence, and creativity going. Not everyone can commit to a full weekend away, and these options give women meaningful ways to connect in a way that fits their life.

Ultimately, I want The Retreat Co to be a year-round ecosystem where women feel supported, empowered, and themselves on the mountain, around the campfire, online, in their normal life and soon, at our new retreat property in the mountains near Tahoe!