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At Winni Media, our mission is to create and implement "win-win" B2B and B2C strategies that help businesses achieve their marketing goals.  

Winni Media | Our Mission

Sandy Cleary

CEO and Founder

Winni Media founder, Sandy Cleary, a.k.a. The High-Heeled Investor®,  is a rocket-scientist-turned-entrepreneur that turned her passion for cruising into a $135+ million dollar business that she built from the ground up and later sold to a $24 billion-dollar travel powerhouse.


Sandy has always had a passion for marketing, and she believes that forging strong partnerships is critical to the success of any business. Sandy, along with her team at Winni Media, pioneered a first-of-its-kind partnership between a travel agency and TV retailer, HSN, to showcase cruising to HSN’s audience of 90 million consumers.  After witnessing the heartbreaking and devastating impact that the pandemic had on her much loved travel industry, she decided she wanted to “jump back in” and be a part of the industry rebuild. She worked with her Winni Media team to develop a multifaceted process that benefits consumers, travel suppliers and agents alike. The value of this process was that it was not only affordable but also increased potential leads, converted more sales, introduced first-timers to the joy of travel, as well as keeping the interest of veteran travelers piqued. Visit Winni Wanderer™.

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  • Sandy Cleary's LinkedIn

Darlene Carenza

Director of Marketing and Strategy

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As the Director of Marketing and Strategy, Darlene manages the Winni Media team and directs the overall business strategy and day-to-day operations.  She brings more than 15 years of experience in Marketing and Partnerships at brands such as Sony Pictures, Cotton Incorporated and CBS Sports. At Travelzoo, Darlene oversaw the cruise category in North America and worked closely on strategic marketing campaigns with both cruise lines and cruise agencies.


When Darlene is not meeting new partners, strategizing with her team, or writing and editing copy (a passion of hers), she can be found advocating for kids with food allergies or at Disney World with her husband and daughter Parker.

  • Darlene Carenza's LinkedIn


At Winni Media, we are big on teamwork. Our team of marketing professionals, content creators, and audience growth specialists are behind the scenes putting their heart and soul into bringing brands together, building successful lead generation campaigns, and creating content for our Winni Wanderer ® publication. We are passionate about what we do, and we value both our consumers and our brand partners, which is why we are committed to creating “win-win” opportunities for all.

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