Winnie Park's Turnaround of Five Below: A Retail Success Story

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Imagine stepping into the CEO role of a struggling retail giant during the chaos of holiday shopping, with the stock price cratering and customers drifting away. That's exactly what Winnie Park did in December 2024, turning Five Below from a faltering discount chain into a powerhouse with shares surging 85% in 2025. This is the underdog story of an executive who wasn't a household name but became the complete package for a retail turnaround.[1]

Early Days: From Retail Veteran to Crisis Commander

Winnie Park's journey to Five Below's top spot reads like a retail resume built for battle. Before her appointment, she had steered Forever 21 through turbulent times and revitalized Paper Source as its CEO. Her career also included high-stakes roles at Duty Free Shoppers, Levi's, and even a stint on McKinsey's retail team. Analysts described her as an "unknown quantity" on Wall Street, but her decades of hands-on experience in merchandising, supply chains, and operations made her uniquely equipped.[1]

Five Below, the Philadelphia-based retailer targeting tweens and teens with trendy, affordable goodies, was in rough shape by late 2024. The company had endured four straight quarters of negative or flat comparable sales, a stark contrast to its earlier growth fueled by nonstop store openings. Existing locations failed to excite shoppers amid rising shoplifting, fierce competition from e-commerce disruptors like Shein and Temu, and a merchandising mix that had strayed from its core audience. The stock had plummeted to a third of its 2023 peak, leaving investors skeptical.[1]

Park joined mid-holiday rush, a make-or-break moment for any retailer. "When she came in, it was a question of how she was going to fix this business immediately," recalled Mizuho retail analyst David Bellinger. Park didn't flinch. She dove straight into collaboration with cofounder and executive chairman Tom Vellios and chief operating officer Ken Bull, assessing every corner of the operation with the precision of someone who'd seen retail's ups and downs.[1]

Her first challenge was clear: the stores weren't resonating. Items like luggage appealed more to adults than the target tween and teen crowd. Park saw an opportunity to reset, drawing on her rich background to reconnect the business with its roots. It was the classic underdog setup—take over a sinking ship, rally the crew, and bet everything on getting back to basics.

Key Milestones: Pivots, Products, and Profits

Park's turnaround kicked off with a merchandising overhaul. She reset the sourcing teams, directing them to stock what kids actually wanted: hot brands like Lilo & Stitch, SpongeBob, and Hello Kitty. "They loaded the store up with these good, well-known brands, which lifts the whole store," Bellinger noted. This shift away from mismatched adult items created buzz and relevance overnight.[1]

To amplify the excitement, Five Below ramped up social media efforts, drawing in fresh shoppers who hadn't visited in years. Operations got a makeover too. Park simplified store layouts and processes, investing incrementally in labor to boost in-stock rates and customer service. Employees could focus on what mattered, leading to smoother experiences and higher sales per visit.[1]

• First Revenue Wins: Early 2025 saw comparable sales turn positive, breaking the slump as refreshed stores pulled in bigger baskets.
• Pivot from $5 Ceiling: Park boldly moved beyond the strict $5 price point, introducing value-packed items up to $30. "You could find value in that $30 item. It's all relative," one analyst observed, repositioning Five Below as the "Costco for kids"—a place for birthday hauls that sparked repeat visits.[1]
• Stock Surge: By mid-2025, shares had climbed 85%, outpacing most retail peers and even Nvidia, validating Park's vision.

These weren't flashy tech pivots but gritty, fundamentals-first changes. Average store sales hovered at $2.1 million annually, but analysts eyed potential for $3 million or more under Park's initiatives. Her leadership proved that in retail, execution trumps hype.[1]

"Winnie Park is the type of leader that has a very clear vision for the business. She doesn't really overcomplicate things." — Neil Saunders, Global Data retail analyst[1]

Behind the scenes, Park's days were grueling. Coordinating with suppliers during peak seasons, training store teams remotely, and fending off doubters required relentless energy. Yet milestones stacked up: holiday sales rebounded, new stores outperformed expectations, and the company silenced critics who questioned an outsider's fit.

Lessons Learned: Practical Insights for Founders

Park's story offers hard-won wisdom for any founder navigating a slump. Here are three standout lessons, drawn from her playbook and analyst insights.

1. Bet on Fundamentals Over Flash: In the rush for innovation, don't lose sight of basics. Park refocused on customer desires and smooth operations, proving that laser-sharp merchandising and store efficiency can reignite growth. Early-stage founders often chase trends; instead, audit your core offering weekly—what's resonating, what's not?
2. Leverage Your Full Experience: Park wasn't a celebrity CEO, but her "complete package" of skills across merchandising, supply chains, and strategy made the difference. Indie hackers, take note: your varied background is your superpower. Map past roles to current pain points; that cross-pollination sparks breakthroughs.
3. Be Willing to Let Go: Ditching the $5 price anchor was risky but freed the business to capture more value. Founders cling to sacred cows—pricing models, features, even team structures. Test ruthlessly: if it's holding you back, evolve. Park's pivot turned a discount store into a destination, boosting baskets and loyalty.

These aren't theoretical; they're battle-tested. Global Data's Neil Saunders highlighted how Park's holistic grasp avoided common CEO pitfalls, like siloed expertise.[1] For bootstrapped teams, this means prioritizing what scales sustainably.

The Road Ahead and a Call to Underdogs

Today, Five Below stands taller, with expectations high for 2026. Park's changes hint at a structural shift, not a fleeting holiday boost. Investors watch if levers like expanded assortments and optimized stores sustain momentum. From crisis hire to transformational force, Park embodies the underdog founder spirit—proving that with vision, grit, and smart resets, even the toughest turnarounds lead to epic wins.

What is your biggest takeaway from Winnie Park's journey? Have you executed a bold pivot in your own startup? Share your thoughts and stories in the comments below!

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