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Influential Women: Cara Sylvester, Target

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MINNEAPOLIS — Last May Cara Sylvester was appointed to the new position of chief guest experience officer for Target, a post that carries a staggering range of responsibilities. Her portfolio includes marketing; media and creative strategy; Target’s loyalty program, Target Circle; its in-house media company, Roundel; and e-commerce. If that were not enough, she also oversees Target’s enterprise technology systems, data analytics and business intelligence strategy.

influential womenSylvester prepared herself early on for an impressive career in business, graduating from the University of Illinois at Urbana-Champaign and earning an MBA from the Kellogg School of Management at Northwestern University. Since joining Target in 2007 from Deloitte Consulting, she has moved up steadily through the managerial and executive ranks, compiling a strong record of achievements along the way. 

Sylvester first served as senior manager of corporate strategy, then joined the merchandising organization in 2009. In 2017 she was promoted to vice president of beauty, where she led the launch and evolution of Target’s Beauty Concierge program, the first of its kind among mass market retailers. Two years later she was promoted again to senior VP of merchandising for home, a key business for Target, where she drove significant sales and market share growth while increasing the category’s digital penetration to the leading position at the retailer. 

In 2021 Sylvester was elevated to executive VP and chief marketing and digital officer, where she has helped shape Target’s omnichannel shopping experience. Her current post is a natural career step, reflecting her conviction that success in omnichannel retailing depends on the quality of a retailer’s connections with its customers. 

Cara Sylvester

Cara Sylvester

“When you interact with the Target brand, whether you’re walking in our stores, whether you’re picking up a drive-up order, whether you’re seeing our marketing in the world, we want you to feel something,” Sylvester explained during a panel discussion at the National Retail Federation convention in January. “Those feelings that are invoked are because we think about designing our guest experience around a deep emotional connection with our guests, not a transactional or linear one.”

Not surprisingly, Sylvester and her team were given the role of defining Target’s culture, a task that involved exploring with its 400,000-plus team members what it means to work at Target. That process produced a succinct but powerful statement.

“Our culture, very simply, we define as the ability to care, grow and win together,” Sylvester said. “When you care for your team first, they will care for your guests, for your customers, for your community.”

What that means, she added, is investing in team members, listening to team members and looking for ways to make their jobs easier. “I would say we listen to our team deeply and continuously, just as much as we listen to our guests, if not more,” Sylvester elaborated. “That’s where we can actually understand what’s going on in their lives, so that we can appropriately assess their wants and their needs and make ­adjustments.”

That culture of caring transcends the company’s relationship with its team members and directly shapes the guest experience, which has been central to Target’s success. 

“When our guests feel seen, when they feel heard, when they feel cared for, that all adds up to more joy in their lives, which is what we’re all here to do,” she summarized.


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