“I’m C.E.O., but I’m really just a big fan of everybody,” said Mindy Grossman, introducing herself at the Weight Watchers International headquarters in Manhattan. It was a brisk Wednesday afternoon in March and about 100 people, some beaming in from San Francisco, had gathered in a large, brightly lit room above what used to be known as the Ladies’ Mile of Sixth Avenue.
This was not one of the company’s famous “meetings,” held since it was founded in 1963 by Jean Nidetch, a Queens housewife once described as “a svelte 5-foot-7 platinum blonde with a voice like Ethel Merman’s,” during which members submit to weigh-ins and discuss the challenges of trying to eat sensibly.
Rather, it was that most 21st-century of office meetings: a hackathon with engineers and user-experience experts presenting new software ideas for “dub-dub,” as Weight Watchers is affectionately known among some digital natives. The contest was being judged “American Idol”-style by Ms. Grossman, 60, and several of her executive colleagues.
Fortified by bananas (zero SmartPoints, which dub-dubbers track instead of calories), a squash salad (two SmartPoints) and pizza (an alarming seven-to-eleven SmartPoints per slice), goofily named teams stood up to show off their innovations as Ms. Grossman — golden-haired, Gucci-clad, glamorous — interrogated them with regal kindness.
A group called Salty Terror demonstrated voice-guided recipe instruction, which sounded as if Siri had entered a surgical theater. (“Three mid-sized prep bowls.” “Next.” “Strainer.” “Next.” “Knife. “Repeat.” “Knife.”) Another, named G1 after the original Android phone, proposed a menu scanner for easier tracking of SmartPoints in restaurants.
This pleased Ms. Grossman, who is also on the board of directors of the casual-dining conglomerate that owns Outback Steakhouse. “I remind them all the time that if Bloomin’ Onion is 75 points, they need to work on some healthy options,” she said, referring to the battered and deep-fried concoction cut like a flower and served with a mayonnaise-based dipping sauce.
Most captivating was a team addressing the practice of privately pecking points and ingredients into smartphones. “Why does it have to be so awkward to do Weight Watchers with friends?” a product designer wondered rhetorically. “What if there were an easier, more social and more interactive way?”
With their solution, you would never track alone, but rather share “Swishpoints! From my phone to your phone in one quick … ssss … swish!”
“Ahhhh!” murmured the crowd admiringly.
A presenter described User A (a “swisher”) imparting a menu to User B (a “swishee”), with herself hypothetically subtracting the wine from the menu — as if Edward Albee’s “Three Tall Women” had suddenly been outfitted with iPhones and concerns about their body mass indexes. (Wine, incidentally, is the second most common drink tracked by members, outranked only by coffee.)
Soon after came a team called The Incredibles, proposing a sort of match.com for sharing recipes. “Swiping right adds it to your ‘soul foods,’” said the lead Incredible. “Mindy is always talking about personalization. I don’t mean to call you out,” he said to the top boss, “but it’s true.”
Ms. Grossman grabbed the microphone. “Personalization,” she stage-whispered, to hearty chuckles.
Ms. Grossman’s tenure of just under a year has not all been so lighthearted. In February, she encountered her first public relations crisis when Weight Watchers announced during a global employee event that it planned to offer free six-week memberships to teenagers. The well-oiled social media opprobrium machine heaved into gear, with the Balance Eating Disorder Treatment Center introducing an aggrieved hashtag, #wakeupweightwatchers, and the Academy for Eating Disorders posting an open letter to Ms. Grossman that cited studies linking restrictive diets during adolescence to potentially severe mental and physical consequences.
The following month, Oprah Winfrey — who in 2015 bought a 10 percent stake in Weight Watchers, along with becoming its spokeswoman — sold a quarter of that stake, prompting speculation about her long-term involvement. (Ms. Winfrey later said that she was donating some of those shares to a charity and that she remained committed to the company.)
Sitting in a fabric-lined boardroom with the company’s senior vice president of corporate communications, Stacie Sherer, Ms. Grossman was as measured as a cup of popcorn (up to two SmartPoints) about the teenager kerfuffle.
“Whenever you do anything that’s different from the norm, you’ll have some people who think it’s the most incredible thing in the world, that you’re going to help generations get healthy,” she said. “And then you’re going to have some people who want to weigh in thinking that we’re putting the teenagers of the world on a diet which is exactly what we’re not doing.” She cited the company’s consultation with pediatric experts. “There’s nothing that we’re going to do that’s not rooted in science, and that doesn’t make sense,” she said, “ and so it’s just a matter of clarification and communication.”
She herself was an awkward-aged 14-year-old in the Long Island town of Valley Stream when she attended her first Weight Watchers meeting, taken there by her mother, Elaine Waldman, a homemaker who struggled with health problems as well as the scale. “It was mostly women just having a conversation about food and how they felt, and I remember listening to other people and supporting other people,” Ms. Grossman said. She lost about 10 pounds on the program, felt better about herself and joined her high school’s cheerleading squad.
Mindy’s father, Donald Waldman, worked nights for Candy Brand Tomatoes in St. Albans, Queens; he and her mother had tried unsuccessfully for a dozen years to have a baby on their own and hadn’t been able to afford adoption until one night his boss gave him a check earmarked for that purpose. Told this story for as long as she could remember, their daughter developed a strong sense of filial obligation. She went to Manhattanville College a year early, transferring to George Washington University as a senior, and majored in English literature and philosophy with plans to become a lawyer.
A sudden, if unfocused, epiphany came after a summer working as receptionist and occasional fit model for the company that made Nik Nik, the brightly patterned polyester shirts popular during the disco years. She broke an engagement to her high-school boyfriend and telephoned her parents.
“I’m moving to New York,” she announced, to horrified silence.
Her graduation was in 1977, when the city was dangerous and dirty. She found an assistant job at another shirt company, Manhattan Industries, which paid $15,600 a year, and moved into a 330-square-foot studio apartment in an elevator building on First Avenue between 73rd and 74th Streets. The long bus ride to the west side cost 50 cents. “I’d be scrounging, looking for the quarter,” said Ms. Grossman, who is currently renovating a $5.65 million condo at United Nations Plaza.
She moonlighted one winter as a server at Cachaca, a nightclub on 62nd Street above the better-known discothèque Hippopotamus, to make extra cash for the holidays. “You know what? It was fabulous,” she said.
Her career in shirts progressed to the men’s wear brand Enro. One day, the fashion designer Jeffrey Banks arrived there for a meeting and spotted Mindy Waldman handling a busy front desk. “I watched this young woman — 21, 22 years of age — dealing with irate salespeople and messengers, doing it so calmly and efficiently — I was just so captivated by her,” he said in a phone interview. She would eventually become his vice president of sales, part of a rare convergence of talent that included the then-unknown designers John Varvatos and Isaac Mizrahi.
Later, she worked for Willi Smith, a lover of bright color who collaborated with artists like Barbara Kruger and Keith Haring. “Literally the first designer to really articulate that fashions should come from the street up not the top down,” Ms. Grossman said. “To bring democratization to fashion, before Target ever thought of it.”
Mr. Smith died of AIDS-related causes in the spring of 1987. Later that year, a month before her 30th birthday, Mindy Waldman married Neil Grossman, a mathematical physicist turned lawyer turned financier. They have a grown daughter, Elysabeth, nicknamed Lizzy, and a 15-month-old granddaughter, Emma. “It’s fabulous, it’s so unbelievable, I’m obsessed,” Ms. Grossman said, adding brightly of Lizzy: “And she’s on the whole Freestyle and loves it, because a lot of today’s young moms, they have to be healthy for their kids.” (Under the Weight Watchers Freestyle system introduced in December, more than 200 foods including beans, peas, chicken breast and seemingly every fish in the sea can be consumed with wanton abandon.)
She went from Mr. Smith’s company to then-fledgling Tommy Hilfiger, as vice president of sales and marketing, and then to the aesthetically similar Ralph Lauren as the president of its bridge line, Chaps. Later, she started Polo Jeans, which was directed at young people, and which has remained one of Mr. Lauren’s most successful and enduring brand extensions.
Ms. Grossman’s next stop was Nike, where she expanded the apparel business by over a billion dollars, with a particular focus on women’s wear.
But she was eager to be a chief executive, and after a recruiter from Barry Diller’s InterActive Corp. contacted her about heading its retail division, she sold Mr. Diller on a plan to revive the then-ossified Home Shopping Network.
Inspired by the chatty format of her favorite cooking shows, Ms. Grossman brought higher-end labels and A-list celebrities including Jennifer Lopez and Serena Williams to the channel, along with much-heralded new Herman Miller Aeron chairs. In August 2008, spun off from IAC by Mr. Diller, Home Shopping Network went public. A month later came the fall of Lehman Brothers and subsequent international financial crisis.
“All I could think about were the 6,000 people that worked for the company — their families, their future,” she said. “I was so stressed out.”
For the next year, Ms. Grossman focused on bolstering company spirit. “Number one, there’s never any bad news on H.S.N.,” she reassured her employees. “Number two, even if somebody cannot afford to do business right now, I want them to think that we’re a place they could go to be a part of the community, or interface with the brands they love, because it’s the nature of the business, and it’s not about selling.”
She remained there over a decade, and the network’s fortunes mostly rose. With waterfront property in St. Petersburg, Fla. and a house with vineyard in Millbrook, N.Y., Ms. Grossman considered retirement, but the opportunity to run Weight Watchers intrigued her. The financial returns are less important to her, she insisted, than freshening a brand that, with its cruises and oft-deserted storefronts, some considered as stale as an outdated package of SandwichThins (three SmartPoints).
“I’m not the turnaround girl — I’m the transformation-growth person,” she said.
On Thursday, Ms. Winfrey, a little out of breath after a 45-minute run, praised Ms. Grossman, one of around five candidates brought to her by a search firm. “She’s an executor and a doer, not just a sayer and a talker,” Ms. Winfrey said during a phone interview.
“The thing that did it for me was that she understood immediately that it was a lifestyle and not a diet, and that we were still operating as though it was a diet,” she went on. “She said the same things that I had also felt and expressed, that it allows for your own accountability, but it’s really so much more than that, so that was music to my spirit.” (And how many FitPoints had that run earned Ms. Winfrey? “I don’t count them, because it’s so ridiculous!” Ms. Winfrey said. “If I were to count them, probably it would be four, and it would be so irritating.”)
Weight Watchers has long had to fend off other programs like Nutrisystem, Medifast and Jenny Craig. But the new millennium has also brought competition in the form of free tracking apps like MyFitnessPal and LoseIt! “I keep doing the research and I realized that our greatest competition is people thinking they can get healthy themselves,” Ms. Grossman said.
Then there has been the rise of gleaming, “aspirational” alternatives like Gwyneth Paltrow’s Goop and boutique fitness classes. “There’s a portion of wellness that seems for a small few,” Ms. Grossman said diplomatically, “and we think wellness should be part of everyone’s life and accessible to all.” (Weight Watchers’s membership costs range from about $3 per week for an online-only plan to $12 a week with personalized coaching.)
She has countered the industry’s largely middle-of-the-road rotation of celebrity endorsers like Marie Osmond (Nutrisystem) with the of-the-moment music producer DJ Khaled, who has embarked on a tour of various cities with a food truck. Fond of gardening, he has boasted of a 26-pound weight loss — though this week he came under fire for pouring vodka (only three SmartPoints, but still!) over his breakfast cereal.
Whether because of such moves, or the wind beneath her wings of Ms. Winfrey, Weight Watchers during a February earnings call announced a 23 percent increase in subscribers from the previous year and set a goal of $2 billion in revenue, up from the present $1.3 billion, by 2020.
“Mindy loves a challenge,” Mr. Banks said. “In any job that’s she ever had, she’s had a mind like a computer.”
In the hackathon’s deliberation chamber, Ms. Grossman did not seem as enthralled with SwishPoints as her fellow judges: “I just question — really, how much utilization is that really going to get? I don’t know if you’re the mom, and you do it — the big thing you want to do is now be swishing?”
The executives huddled in heated discussion for a few minutes, and then filed out so that Ms. Grossman could announce the results. Third prize went to a team that had figured out how to livestream Weight Watchers meetings to users who couldn’t show up in person. Second was G1’s menu scanner. First place was a tie between two of the teams.
“We believe there’s a big opportunity if The Incredibles and Swishpoints had a baby, seriously,” Ms. Grossman said with a broad smile, and thanked out-of-towners for making the trip.
“As much as we believe in technology,” she said, “having people together is also pretty fabulous.”
And it was time for a beer at the happy hour — two to six SmartPoints, depending.
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