Gregg Coccari <99% TESTED>

Gregg Coccari: The Strategic Architect of EdTech Growth Gregg Andrew Coccari is a seasoned executive and serial CEO known for leading major digital transformations across multiple industries, most notably steering the global online learning platform Udemy through its initial public offering (IPO). With over 30 years of leadership experience, Coccari has built a reputation as a specialist in scaling high-growth companies and transitioning private entities into public powerhouses. Early Life and Education Coccari pursued his undergraduate studies at Colgate University, where he earned a Bachelor’s degree in Psychology. He later received his MBA from the Wharton School of the University of Pennsylvania, an institution frequently ranked among the top business schools globally. Despite his eventually high-profile career, Coccari has noted that he did not have a clear career path immediately after college, only realizing in his late 20s that he wanted to run his own company. This realization prompted his return to business school to acquire the necessary strategic tools for executive leadership. Professional Career and Leadership Roles Before entering the EdTech sector, Coccari held several senior executive positions at diverse service-based companies: Teleflora: Served as President and CEO from 1992 to 2004, overseeing the world’s leading floral wire service. NetQuote: Led the insurance lead-generation platform as President and CEO between 2006 and 2009. Futuredontics (1-800-DENTIST): Appointed CEO in 2010, where he focused on expanding the company’s dentist referral and marketing solutions. Stella & Chewy’s: Prior to joining Udemy, he served as the head of this premium pet food company, helping to manage its expansion under investor guidance. The Udemy Era (2019–2023) In February 2019, Coccari came out of retirement to accept the role of CEO at Udemy. His tenure was marked by rapid scaling and a strategic shift toward corporate learning. Udemy Announces CEO Transition

Gregg Coccari is a seasoned executive best known for his recent tenure as the Chief Executive Officer and Chairman of the Board of the global online learning platform Udemy . He is currently retired, having transitioned out of his leadership role in early 2023. Professional Career & Leadership Coccari is recognized as a "turnaround" specialist and growth-oriented leader with over 30 years of experience in the technology and consumer services sectors. Udemy (2019–2023): Coccari joined Udemy as CEO in February 2019, coming out of a brief retirement to lead the company through a period of massive expansion. Under his leadership: The company experienced significant growth, particularly during the global shift to remote learning. He successfully led Udemy through its Initial Public Offering (IPO) in October 2021. He retired from his roles as President, CEO, and Chairman effective February 28, 2023 , transitioning to a transitional advisory role for the company. Previous CEO Roles: Prior to Udemy, Coccari held chief executive positions at several prominent companies, including: Stella & Chewy’s: A premium pet food brand. Futuredontics (1-800-DENTIST): A dental marketing and lead generation service. NetQuote: An online insurance lead generation company. Teleflora: A floral wire service company. Education & Personal Background Education: He holds a B.S. in Psychology from Colgate University and an MBA from the Wharton School of the University of Pennsylvania. Interests: Outside of the boardroom, Coccari is an avid hiker and exercise enthusiast. He is passionate about education and has expressed a preference for "human interaction" over remote digital communication. Residence: He is based in Santa Monica, California .

With 150,000 courses ranging from how to win at online poker to principles of quantum mechanics, online education startup Udemy is... Forbes Document 2 - file: udemy-consultingagreementf.htm - SEC.gov Consultant's equity incentive. Consultant will continue to be deemed a “Service Provider” under the terms of such Plans. agreed up... SEC.gov 7 sites Gregg Coccari came out of retirement to take Udemy to next ... Aug 5, 2022 — gregg coccari

From the Rink to the Boardroom: The Leadership Journey of Gregg Coccari In the high-stakes world of specialty retail and brand management, success often hinges on the ability to adapt, endure, and lead with a steady hand. Few executives embody these principles as clearly as Gregg Coccari , a former collegiate hockey player who has spent nearly two decades steering one of the world’s most iconic outdoor equipment retailers. As the former Chairman, President, and CEO of Sierra Trading Group (formerly Sierra Trading Post) and a long-time executive at Mills Fleet Farm , Coccari has built a reputation as a turnaround specialist and a leader who understands the gritty realities of both the playing field and the sales floor. Early Life and Athletic Discipline Gregg Coccari’s professional identity was forged long before he entered a corporate office. A native of New England, Coccari played NCAA Division I hockey for the University of Vermont (UVM) from 1980 to 1984. As a goaltender for the Catamounts, he learned the value of resilience, quick decision-making under pressure, and the importance of being the last line of defense—skills that would later translate directly into corporate crisis management. Coccari graduated from UVM with a degree in Business Administration, immediately bridging his athletic discipline with a career in sales and management. The Fleet Farm Years: Mastering the Big Box Before his rise to national prominence in the e-commerce space, Coccari spent over a decade at Mills Fleet Farm , a Midwestern chain of big-box retail stores catering to farming, automotive, and outdoor enthusiasts. Starting as a General Manager, he climbed the ranks to become Executive Vice President of Merchandising and Logistics. During his tenure (1997–2008), he was instrumental in optimizing the company’s supply chain and merchandising strategy, helping transform Fleet Farm from a regional farm-supply chain into a more competitive, modern retail force. This period honed his expertise in hard goods, workwear, and outdoor gear—a foundation that would define his future. The Sierra Trading Post Turnaround (2008–2020) Coccari’s defining career moment arrived in 2008 when he was brought in as President and CEO of Sierra Trading Post , then a niche, catalog-based off-price retailer of outdoor gear. At the time, the company was solid but struggled to scale in the shadow of giants like REI and Amazon. Coccari executed a three-pronged strategy:

Digital Transformation: He aggressively pivoted the company from its print catalog roots to a high-efficiency e-commerce model, investing heavily in website user experience and digital marketing. Off-Price Dominance: He doubled down on the “treasure hunt” model—offering deep discounts (30-70% off retail) on over 700 top outdoor and activewear brands. This created fierce customer loyalty. Operational Efficiency: Leveraging his logistics background from Fleet Farm, he streamlined Sierra’s distribution network, cutting costs without cutting quality. Gregg Coccari: The Strategic Architect of EdTech Growth

The results were dramatic. By 2012, Sierra Trading Post was consistently ranked among the fastest-growing companies in America by Inc. Magazine . The turnaround caught the attention of the retail giant TJX Companies (owners of T.J. Maxx, Marshalls, and HomeGoods). In December 2012, TJX acquired Sierra Trading Post for an undisclosed sum, widely reported to be in the hundreds of millions. Coccari remained at the helm, and under his leadership, Sierra (rebranded as Sierra in 2018) expanded from a single warehouse in Cheyenne, Wyoming, to a multi-channel powerhouse with dozens of brick-and-mortar stores across the U.S. He stepped down as CEO in 2020 but remained Chairman of Sierra through the transition, overseeing the brand’s continued integration into the TJX family. Leadership Philosophy: "The Goalie Mentality" In interviews, Coccari frequently cites his hockey background as the blueprint for his management style. “As a goalie, you can’t dwell on the last goal,” he told Wyoming Business Report . “You reset, you watch the play develop, and you react. In retail, the market scores on you every day—a bad quarter, a supply chain glitch. You clear your head and focus on the next shot.” Colleagues describe him as a servant leader —approachable, detail-oriented, and unusually calm during periods of rapid growth or industry disruption. He is also known for championing a “team-first” culture, believing that the best ideas often come from warehouse staff and store associates, not just corporate VPs. Post-CEO Career and Legacy Since leaving the day-to-day CEO role at Sierra, Coccari has remained active in the outdoor industry. He serves on the Board of Directors for several private equity-backed consumer goods companies and acts as an advisor to emerging outdoor and active lifestyle brands. He continues to reside in Wyoming, an environment that suits his passion for fly fishing, skiing, and mountain biking—activities he says keep him connected to the customer. Key Takeaways

Turnaround Expert: Transformed a catalog-based off-pricer into a digital juggernaut, leading to a successful acquisition by TJX. Operational Acumen: Merged logistics discipline from big-box retail with the agility of e-commerce. Athlete-Leader: Pioneered the concept of “goalie mentality” in corporate resilience. Outdoor Authenticity: A genuine enthusiast who built a brand trusted by serious climbers, skiers, and campers. He later received his MBA from the Wharton

Gregg Coccari’s career is a case study in how niche retailers can survive—and thrive—against industry titans. By staying true to the customer, leveraging operational expertise, and maintaining the cool head of a goalie facing a breakaway, he turned Sierra Trading Post from a hidden gem into a national success story.

Note: As a private individual post-2021, Gregg Coccari maintains a low public profile. This article is compiled from historical business records, TJX annual reports, and regional media interviews.

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