Perhaps the most notable résumé gap is her lack of experience in healthcare. She'll inherit predecessor Stefano Pessina's plan to transform the Deerfield-based chain's 9,000 drugstores into "neighborhood health destinations," offering doctor's appointments and other medical care. It's a dramatic transformation that will take Walgreens and its new CEO into unfamiliar territory.
Throw in responsibility for Walgreens' role in the massive COVID-19 vaccination campaign, and it's clear Brewer faces a steep learning curve.
"Despite her impressive accomplishments, she is not a healthcare person," says professor Erik Gordon of the University of Michigan's Ross School of Business. "Walgreens might fall further behind in the race to become a healthcare services provider and instead retreat into what she is good at—retailing."
Brewer has proved adept at homing in on what customers want in a retail experience and delivering, says R.J. Hottovy, a fund manager at Aaron Allen Capital Partners, an investment firm specializing in the restaurant industry.
When Brewer joined Seattle-based Starbucks in 2017, some of the coffee chain's roughly 15,000 stores were struggling to serve both mobile and walk-in customers. Brewer helped figure out what each store needed to be—sit and gather or grab and go. Along with other factors, her changes helped boost comparable-store sales growth to 5 percent in 2019 from 2 percent in 2018.
"She really had an eye for real estate and how it's changing," says Hottovy, who formerly covered Starbucks as an analyst at Morningstar. It's an issue she'll likely tackle right away at Walgreens, which has been working to rev up customer traffic and sales at its stores.
Brewer also helped transform Starbucks' cold beverage program, moving away from gimmicky drinks like high-calorie, Unicorn Frappuccinos toward lower-calorie cold brews and nitro offerings. Cold drinks grew from 45 percent of total beverage sales in fiscal year 2016 to 60 percent in 2020.
"Retail's not dead in the age of Amazon; it's just bad retail is dead," says Hottovy. "Walgreens hasn't made it enjoyable enough to shop the front of the house, the nonpharmacy side of it, and I think that is going to be something they can rely heavily on her for."
Brewer has also been front and center with investors, explaining that the pandemic accelerated plans to transform stores to more convenient formats, and how Starbucks has relied on mobile to help with recovery.
Less encouraging is the performance of Sam's Club during Brewer's five years at the helm. After rising 4 percent in 2013, comparable sales grew 0.5 percent or less for the remaining four years of her tenure, Walmart filings show.
Meanwhile, archrival Costco posted mid-single-digit growth, says Zain Akbari, an analyst at Morningstar covering Walmart.
"It seems like top-line growth was a concern when they decided to go in a different direction at Sam's Club toward the end of her tenure," he says.
Growth is a concern for Walgreens, too. Walgreens stock has lost a third of its value since 2015 amid concern over slumping customer traffic and shrinking pharmacy profit margins. Simultaneously, competition from online retailers—namely Amazon, which counts Brewer as a board member until she steps down Feb. 16—has eaten away at sales on the front end of the drugstore.
To be sure, Brewer notched some successes at Sam's Club, particularly on the technology front. She launched scan-and-go payments, which Walmart says drove customer traffic and spending. The store's Club Pickup feature grew 31 percent in fiscal 2017, with enhanced features like mobile check-in and prepayment.
Under Brewer, Sam's also moved many of its back-end functions from paper-heavy manual processes to a Salesforce cloud platform. The switch improved productivity and helped integrate in-store and online shopping channels, says Amanda Lai, manager at retail consulting firm McMillanDoolittle. That kind of experience could help Walgreens catch up with rivals CVS and Walmart in the digital realm.
Pessina, who has been in charge since 2015, touted Brewer's digital expertise when he announced her hiring. If Brewer can help improve store traffic and mobile offerings, it would make Walgreens—which is still in the "beginning innings" of digital—more competitive, says Elizabeth Anderson, an analyst covering Walgreens at Evercore ISI.
But the most daunting challenge facing Brewer and Walgreens will be the company's planned transformation into a healthcare provider. Walgreens has formed a partnership with VillageMD to put doctors into 500 to 700 stores over the next four years. The $1 billion project includes adding up to 9,000 square feet of clinic space to the drugstores.
Walgreens' main drugstore rival is taking a different approach to healthcare. CVS expanded into insurance with the acquisition of Aetna and also owns a pharmacy benefits manager. Anderson says the hiring of Brewer confirms Walgreens will rely more heavily on its stores.
"They're zigging and everybody else is zagging," she says. "We don't know for sure whether the zigging . . . is ultimately going to play out. . . .But they need something."
Also unclear is how much autonomy Brewer will have in a C-suite full of Walgreens Boots veterans who have worked with Pessina for years. The company's co-chief operating officers are Ornella Barra, who is Pessina's life partner, and Alex Gourlay, who joined Boots in the 1970s and worked his way up.
Pessina will remain as executive chairman. The Italian billionaire is also the largest single shareholder, owning almost 17 percent of Walgreens' outstanding stock.
"Given the fact he's taken the role of executive chair, and the fact that he has this significant stock, means her role, like it or not, will be more limited," says Charles Elson, professor of corporate governance at the University of Delaware. "Executive chair will still call the shots."