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Jul 30, 2023

Outside Brands – Build on Successful Heritage With Woman-Led Leadership Team

Celebrate Hilton Head Magazine

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“Outside Brands will continue to grow with our three-discipline model of retail, leisure recreation, and destination management, with a focus on the Lowcountry of South Carolina and the Georgia Coastal Empire. We are regularly adding new experiences, services and retail offerings."

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A group enjoying an Outside experience off the coast of Hiton Head Island aboard the Outside Owl.

Many people already know about Mike Overton’s success story in founding and building Outside Brands as well as his commitment to the Lowcountry’s environment and community. From humble beginnings as a windsurfing school in 1979, Outside Brands has grown into a dynamic four-division business with operations in South Carolina and Georgia. Driven by a mission to enrich lives by connecting people to exceptional places, products and experiences, Outside Brands offers fully customized group travel services, team-building programs, activities and specialty retail.

What is less well known is the depth and breadth of the female-led management structure he continues to invest in. Raised by a strong woman, Overton was inspired to ensure that women have always had every opportunity to develop their careers in his company. “I am so proud of the women of Outside Brands, that lead our organization,” he said. “My mother, Ellen Overton, dedicated her life to working toward the goal of a society that provided gender equality in the workplace. Outside is a product of this legacy.”

In recent months, many amazing women have been appointed to the Outside Brands leadership team, who are in the forefront of ecotourism, sustainability, and local business within the Lowcountry. This impressive and important commitment to developing and supporting tomorrow’s leaders is apparent and is adding to the already significant legacy Overton has built. With the appointment of Sharon Sutton as their new director of human resources, Sarah Tillman as the company’s chief financial officer, Jennifer Messier as their new director of risk management and strategy, and Anne Kelley as the Outside destinations management (DMC) team’s new business development manager, he has surrounded himself with a talented group of women to continue growing the company.

The 2023 Outside Brands Team

In the specialty retail arena, Jessie Madden heads the department as the new director of retail, with both the company’s men’s and women’s retail buyers being women-led as well. Madden oversees all three Outside retail locations, including Hilton Head Island, Palmetto Bluff, and Savannah, with the vision to enrich lives by connecting people to exceptional products with a sustainable mission. She enjoys getting to know the consumers and what makes their lives richer through the stories they tell from products they found while shopping at Outside.

“What inspires me about being part of the Outside Brands Team is the freedom to think outside the box,” Madden said. “Here, we are given the ability to bring in local vendors and give the ‘little guy’ a chance to get their product off the ground. We are also encouraged to create ways to give back to our community with initiatives like our charitable Recycle Your Jacket campaign and by sponsoring Pint Nights, which is next happening in September as part of Paddle Battle weekend.”

“Almost all our leadership team positions are held by women. These individuals are a team of no-nonsense, get-the-job-done, straight-shooting people that achieve great things daily,” Overton said. “All appointments are given to the most qualified candidates. In today’s workplace, simply put, we have found the most qualified applicants we interview and vet to be women.” 

Overton has always been forward thinking, and the appointment of the next generation of female leaders as well as the opportunities for career advancement and promotion is nothing new at Outside Brands. The number of professional women in the company is inspiring and includes:

Carol Kavanaugh-Arrington, destinations DMC director of sales; Jennifer Freeman, destinations DMC director of operations; Kelle McMichael, director of Outside Palmetto Bluff; Pippi Ikor, marketing manager; Patty Robbins, director of guide training and education; Brittany Willard, reservations director; Jean Fruh, Outside Foundation executive director; Denise Spencer, Outside Foundation board chairperson; and Samantha Valdes, manager – Outside Savannah.

An exclusive sunset trip to Page Island on the luxury catamaran, Outside Ohana.  

Managing marketing initiatives at Outside Brands, Anneliza “Pippi” Itkor said, “I am inspired daily by the commitment of our team. Mike Overton looks for staff who are hungry, humble and smart, and lives these values himself as an example to us all. No matter what your role is in the company, there is a deep appreciation for hard work, and that compels us to bring our very best to this company, day after day.”

On the sales side, Kavanaugh-Arrington said, “Outside Brands lets me be part of a team of dedicated, hardworking, talented individuals who are committed to providing exceptional experiences from being on the water to extraordinary events.”

As the company enters its fifth decade, the leadership continues its successful path. “Outside Brands will continue to grow with our three-discipline model of retail, leisure recreation, and destination management, with a focus on the Lowcountry of South Carolina and the Georgia Coastal Empire. We are regularly adding new experiences, services and retail offerings,” Overton explained.

One way they are growing is through harboring one of the most unique event venues in the Lowcountry—the Outside Ohana—a 47-foot luxury catamaran. The Ohana has quickly become a much sought after gathering place for group outings, family reunions, corporate events, gathering of friends, small weddings, and more. With completely customizable experiences and numerous decor, catering, and activity options, the Ohana is the ideal way to experience the sights and seas.

The Outside Brands Leadership Team (left to right): Sarah Tillman; JC McCune, Sharon Sutton; Jennifer Messier; Jessie Madden; Mike Overton; Kelle McMichael; Brittany Willard; Michael Hodson.

The Ohana was introduced to the Outside fleet in 2020 and comfortably holds up to 49 passengers. It boasts a spacious outdoor deck perfect for taking in panoramic views, a cabin area that can be open-air or weather protected, a state-of-the-art sound system to handle custom playlists, a large bar for food and beverage service and an on-board restroom.

Outside Brands’ team of professionals always work to create the perfect tailored events, with departure locations from Hilton Head Island and Bluffton, South Carolina, and Savannah, Georgia. The women of Outside destinations management team, Outside DMC, assist with local catering options, and the team of experienced local captains and staff are fully equipped for all activities including private island exploration, kayaking, paddle boarding, beachcombing, and tours of the Port of Savannah, the Savannah National Wildlife Refuge, Daufuskie Island, Bluffton, Hilton Head Island, and beyond. 

In addition to private experiences, Outside Ohana features selected shared experiences during specific holidays and times of the year. Shared experiences include dolphin eco tours and beachcombing cruises from Hilton Head Island, and a port tour along the Savannah River. Special holiday experiences include summertime fireworks cruises from Hilton Head Island and the Holiday Parade of Lights in Savannah.

Clearly, Mike Overton has achieved a wonderful balance of inspiring leadership and empowering the next generation to be their best selves. “Outside Brands is committed to being the region’s best place to work,” he said. “This goal is supported via exceptional team training, a focused mission, company growth that fuels career development, and a deep appreciation of our associates.”  

For more information, please visit and follow the organization on Facebook, Instagram, LinkedIn, and TikTok.

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