For those of you who read my article back in November 2021, Is Sonia Syngal Gap’s Fourth “Hail Mary?” you will understand that Richard Dickson, soon to take the helm as CEO of Gap Inc., will be the fifth … Hail Mary. Indeed, the four CEOs preceding him did not score a turnaround of the iconic Gap brand and its three “sisters,” Banana Republic, Athleta, and Old Navy. Sonia Syngal actually had a good run leading Old Navy from 2016 to 2019, which likely catapulted her into the Gap Inc. corner office in 2021. But the rest was history, and a fourth failed Hail Mary attempt.

Anybody who knows anything about Hail Mary passes knows that the team had better have a very long passing capability and a wide receiver whose hands are football magnets. Keeping with the metaphor, over the past three decades, four Gap CEOs have dropped the ball.

Anybody who knows anything about Hail Mary passes knows that the team had better have a very long passing capability and a wide receiver whose hands are football magnets. Keeping with the metaphor, over the past three decades, four Gap CEOs have dropped the ball. To review: Mickey Drexler stepped down in 2002 having guided Gap Inc. through almost two decades of meteoric growth from $480 million in revenues upon his arrival in 1983, to almost $14 billion in 2000 (including his launch of Old Navy and Banana Republic) — an amazing 2,400 percent increase. Drexler’s mind-boggling accomplishment was then followed by three CEOs who had zero apparel experience. And while the fourth led the Old Navy brand for three years, adding $1 billion in growth, she didn’t have the Hail Mary touch to sustain a growth trajectory for Gap Inc.

The Barbie Mastermind Attempts the Fifth Hail Mary

The Gap Board, once again, convincing themselves that “it ain’t over ‘til it’s over,” plucked out the relatively new Board member, Richard Dickson (having joined in November 2022), to become its next CEO. Dickson did have some visibility in apparel, however brief, as President and CEO of Branded Businesses within the mishmash of more unrelated brands than I care to list (over 25) at the Jones Apparel Group. He reported directly to Wesley Card, CEO of the entire enterprise. Dickson lasted from 2010 to 2014 when he returned to Mattel to oversee the magical reimagination and reengineering of the Barbie brand, which at the time was struggling to stay alive. It should be noted that Dickson’s first stint at Mattel as COO (2000-2010) resulted in the successful repositioning of several toy brands, notably Hot Wheels and Fisher-Price. Furthermore, Mattel collaborated with the Gap in April 2022 to create a Gap X Mattel branded line with “Gap X Barbie™ being the first co-brand – a mostly tween+ collection of pink T-shirts, skirts, logo hoodies, denim, button-downs, and accessories. It was all designed with Gap’s product icons featuring classic Barbie branding and Gap’s signature typeface. One could assume that this initial branding experience with Gap led to Dickson joining the Board, which then led to his appointment as president and CEO less than 10 months later. With the runaway success of the movie, one can assume that Gap X Barbie™ will glow in the halo effect of Greta Gerwig’s blockbuster. However, toys are one thing, apparel retailing is totally another. And add to that the necessity to reenergize the Gap, Old Navy, and Banana Republic brands that have been barely treading water for over two decades.  And then there’s Athleta, which in my opinion, never really got off the ground. So, I view the Mattel toy collaboration as a clever marketing gimmick, not a strategic move that will turn Gap’s four existing brands into lightning rod collections as the new and hottest apparel brands that the next gens will stand in long lines to buy.

Can Dickson Throw a Deep Pass into the End Zone?

Richard Dickson has a proven track record in the toy business as a marketing star, especially for the turnaround and excitement about everything Barbie. His short, four-year stint at The Jones Apparel Group seems puzzling. As head of global design and development, including marketing and merchandising, what were his major accomplishments? And the fact that private equity firm Sycamore Partners acquired the Jones business for $2.2 billion in 2013 also raises the question of Dickson’s role in the business. Why did he leave to go back to Mattel? My point is that when Richard Dickson takes the helm of Gap Inc., it will not be warm and fuzzy. The challenges are existential. And I’m not sure if his limited experience at the Jones Apparel Group qualifies him to turn around one of the most storied retailers in the history of the industry.

Two Hopeful Paths

I found two comments made by Richard Dickson that could define his leadership capability to engage the Gap culture and initiate bold strategic moves. The first was about the Barbie success: “So far, the biggest lesson that I and Mattel have learned from the Barbie movie experience is the importance of discomfort and taking calculated risks.” I would add to his lesson that all risks cannot be calculated. Some will be “betting the farm.” And the second comment, perhaps the most important first step in building a long-term brand strategy was, “Why are we here?” I would suggest to any retailer that why you are here and why we matter is not existential; it is the basis for any successful brand. But David Katz, CMO of Randa Apparel and Accessories, may have said it best: “You can’t navigate a new landscape with old maps.” And that might suggest that Dickson’s background may jolt Gap out of its sluggish past. We’ll see.

A Final Suggestion

If Richard Dickson is the kind of leader that Gap Inc. needs, I suggest he surround himself with the best and brightest retail professionals he can find.  And then listen to them. Good luck Mr. Dickson. The Gap portal is opening in only a few days.