Leadership History

Five Below: CEO History

4 leaders · 2002 to present

Company Overview

Five Below is not a traditional dollar store. It is a specialty value retailer with a younger brand voice, brighter store experience, and an assortment built around discovery, gifting, seasonal trends, toys, candy, tech accessories, beauty, room decor, and sports.

4

Winnie Y. Park

Chief Executive Officer

2024 – Present

2 years (current)

Key Decisions & Impact

Appointed CEO in December 2024, Winnie Y. Park was brought in to lead the next major phase of Five Below's growth following a sudden leadership transition. Leveraging her extensive executive experience as the former CEO of Forever 21, she immediately focused on revamping the company's omnichannel strategy, seeking to bridge the gap between the vibrant in-store experience and the brand's digital presence. She prioritized expanding the company's reach on social media platforms like TikTok, recognizing the critical importance of digital marketing in capturing the fleeting attention of the core tween and teen demographic. Furthermore she was tasked with stabilizing store operations, specifically addressing rising inventory shrinkage by re-evaluating the company's widespread use of self-checkout kiosks.

Legacy

Park brings crucial, high-level fashion and lifestyle retail expertise to the discount chain, ensuring that the company's ever-changing merchandise remains culturally relevant and 'trend-right.' Her leadership is focused on navigating complex macroeconomic headwinds while protecting the brand's core value proposition, ensuring that Five Below remains the premier, affordable shopping destination for young consumers.

3

Joel Anderson

Former President and CEO

2015 – Present

11 years (current)

Key Decisions & Impact

As CEO for nearly a decade, Joel Anderson engineered the most dramatic period of expansion in the company's history, scaling the footprint from roughly 360 regional stores to a national network of over 1,600 locations. He made the difficult but essential strategic decision to break the company's foundational '$5 or less' rule, introducing the 'Five Beyond' store-in-store concept to combat rising supply chain costs and introduce higher-margin product categories. He also heavily invested in modernizing the company's digital infrastructure, expanding e-commerce capabilities and revamping the physical supply chain to support rapid national growth.

Legacy

Anderson transformed Five Below from a successful regional player into a bona fide, globally recognized retail juggernaut. His willingness to evolve the core pricing model—a controversial move that many analysts feared would alienate the customer base—proved to be a masterstroke that significantly boosted store profitability. His unexpected departure in 2024 to become the CEO of Petco marked the end of a pivotal, successful era for the brand.

2

Tom Vellios

Co-Founder and Former Executive Chairman

2002 – 2015

13 years

Key Decisions & Impact

Partnering with David Schlessinger to found the company in 2002, Tom Vellios served as the critical operational driving force behind the brand's early success. Drawing on his extensive retail background, he meticulously engineered the unique, high-energy store layout and established the crucial overseas sourcing relationships required to maintain the extreme-value pricing model. He served as CEO during the company's rapid early expansion phase and guided the firm through its Initial Public Offering (IPO) in 2012, before transitioning to the role of Executive Chairman to mentor the incoming leadership team.

Legacy

Vellios provided the essential retail execution required to turn a clever concept into a scalable, profitable enterprise. His insistence on creating a 'treasure hunt' atmosphere ensured that stores remained a frequent destination rather than an one-time novelty. His ongoing presence as a strategic advisor ensures that the company's foundational, energetic culture remains intact.

1

David Schlessinger

Co-Founder

2002 – Present

24 years (current)

Key Decisions & Impact

As the original visionary behind the concept, David Schlessinger recognized an untapped demographic void left by the collapse of traditional mall-based teen retailers. He correctly hypothesized that tweens and teens desired an engaging, autonomous shopping experience catered directly to their specific interests and limited budgets. He established the original, strictly enforced '$5 or less' rule, forcing the merchandising team to innovate and source creative, trendy products that could be sold profitably within that rigid constraint.

Legacy

Schlessinger is the conceptual architect of the entire Five Below brand. His brilliant realization that 'kids want to shop where they can afford everything in the store' established a new category of retail. His entrepreneurial vision and willingness to take a risk after the failure of Zany Brainy resulted in the creation of one of the most successful specialty retailers of the 21st century.

Challenges & Strategic Context

Five Below must protect its value proposition while merchandise costs, tariffs, wages, rent, and logistics expenses rise. It also has to keep stores fresh enough to drive traffic, avoid overexpansion, and make Five Beyond and higher price points additive rather than confusing.

Five Below CEO and Leadership FAQ

Who is the current chief executive officer of Five Below, Inc.?

Joel Anderson currently leads Five Below, Inc., overseeing strategic vision, balance sheet health, and organizational execution in Specialty Value Retail.

What is the CEO's primary strategic agenda for 2026?

Under executive direction, Five Below, Inc. is prioritizing workflow automation alongside disciplined capital allocation to maximize shareholder value.

How has executive leadership guided Five Below, Inc. through past market transitions?

Leadership at Five Below, Inc. has historically navigated industry cycles by restructuring operational priorities and expanding competitive moats.