Cindy Clearwater Makes Waves with Multi-Channel Marketing

For her entire life, Cindy Clearwater dreamed of living in the Caribbean. Her dream came true on the beautiful island of St. Croix in the Virgin Islands, where she now serves as the creative director and content strategist for her business, Cindy Leigh Media, and also runs a popular island travel guide called MyStCroix.VI.

Cindy’s island life began in 2002 when she was working for a startup travel company and moved to St. Croix to establish their Caribbean base. During that time, she developed local business relationships, managed marketing efforts, and helped develop the company’s website. However, the startup didn’t succeed, and in July 2002, her boss asked her to return to Connecticut — but Cindy decided to stay on the island and give her dream another chance.

Setting sail with two businesses

Thanks to her connections with hotels, she became a wedding and event planner at a resort. “After about six months of working for the resort, I decided I wanted to be my own boss,” Cindy said. “So I branched out and started my destination wedding business.”

Alongside her wedding business, Cindy launched Cindy Leigh Media, offering marketing support and graphic design to other local small businesses. “I started branching out and helping wedding vendors and other small businesses here to market their businesses through social media. At that point, I was a partner with Constant Contact, so I started teaching people how to use email marketing.”

As both her knowledge of the island and her wedding business grew, Cindy noticed a pattern — travelers repeatedly asked her: Where should we eat? What are the excursions? What shouldn’t we miss? “I was answering the same questions over and over again, and I knew how to build a website,” Cindy said. Using her marketing expertise, she created a site as a resource that answered the most-asked questions from travelers. “MySt. Croix.VI evolved out of me finding demand and filling a niche in the Virgin Islands.”

With two businesses that evolved out of her passion for the island and experience in marketing, Cindy has many channels and campaigns to manage. She relies on Constant Contact’s AI tools, like Campaign Builder and Content Generator, to streamline her work and execute multiple strategies at once across email and social media.

Casting a wide net on social

Cindy maximizes efficiency by using Constant Contact’s scheduling tool to post on Facebook, Instagram, and LinkedIn. “It saves me time by allowing me to write the initial post and then customize it for each channel. When I use it consistently during the season, it saves me at least 1-2+ hours per week. I love the analytics and inbox features. They contribute to my time savings because I can quickly view comments and reply to those that need a response, even if they weren’t posted using the social posts feature.”

A key reason that social media is a crucial part of Cindy’s multi-channel marketing strategy is that her content helps grow her email list. “Someone might see that post on social media, which gets them interested, and now they’re going to join my email list,” she said. Cindy also considers the elements of social media posts that can tie into her emails to ensure her strategy is cohesive across all channels and relevant for the respective audiences. While certain information and updates should be shared in both places, other content might be more appropriate for social media only, such as short videos.

“When I’m working in Constant Contact, everything is cohesive and works together,” she said. “I find it really valuable to be able to schedule the social media posts.”

Reeling clients in with email

Cindy’s biggest tip for other small business owners is to first make sure they have a sign-up form for their email list on their website from day one, and then share it broadly. “Don’t just leave it on your website. Share it through links in your Instagram stories. When you’re talking to people, share links to it.”

But sharing the link isn’t always enough — it’s important to give people incentives to share their email, and Cindy does this by offering relevant, valuable content to her audience. She sends travel guide newsletters, event reminders, and discounts on the St. Croix-themed calendars she sells.

“I get the loveliest replies from people to my calendar emails. They really do think I’m talking directly to them, and I really am because I have my ideal client in mind,” she said. 95% of the sales she makes from her wall calendars each year come from her email list.

Another key lesson Cindy has learned is that a personal connection is the best way to market your business through email. She realized that her emails were more successful when she talked about what island life was like, and that people wanted to see more of her personality. She used these insights to inform her social media strategy, once again applying her knowledge of multi-channel marketing to her content. “It’s helped me come out from behind the camera a little bit more on social media,” Cindy said.

Navigating multiple channels with Campaign Builder and AI

Because multi-channel marketing is a core part of Cindy’s strategy, she takes advantage of the new Campaign Builder, which uses AI to do the heavy lifting for her. All she needs to do is enter basic information, such as the goal, target audience, and timeframe. “It’s like angels sing when you launch Campaign Builder. In the 15 years or more that I’ve been with Constant Contact, multi-channel marketing has been the thing I am most excited about,” said Cindy. “This is the best thing that’s ever happened.”

Cindy used the tool to execute two multi-channel marketing campaigns with different goals — attracting new customers and promoting her calendar sales. The tool saved her at least two hours of work per week, so she plans to use Campaign Builder to create more campaigns in the future. “I anticipate it will save me at least 3-4 hours per week once I have it up and running,” she said. “The real value is setting it up to work for me in the background, increasing sales while I’m working on other business tasks and projects.”

Campaign Builder is not the only way Cindy uses AI to save time in her workday. She also uses Content Generator to help her write content and give her a starting point. “When you’re a solo entrepreneur like me, you can get stuck in your own head. Use AI like this amazing, brilliant assistant, but still make the content your own,” she said. “I also love that with AI, if I don’t want to use the exact framework, they’re not going to get mad at me. They’re not going to feel bad that I changed something.”

What’s next on the horizon

Cindy has big goals for business growth. She plans to expand MySt. Croix.VI into a global platform to provide information for Gen X female travelers, share the places she’s been, and explain how she travels on a budget but still flies first class. Additionally, she is developing a strategy lab as an offshoot of Cindy Leigh Media, which will include evergreen marketing courses as resources for her clients. “I find that when I’m talking to friends or clients, they’re focused on one thing. Often it’s social media, Instagram, or TikTok, and they don’t see the big picture. I want to push the sense that it’s not all about social media. It’s not all just about email marketing. It’s how they all work together to make it a big superpower.”