Weiner came to Penn State in the early ’90s via Miami, where she’d gone to a performing arts high school. She majored in theatre but soon added two more majors, in classics and women’s studies. The latter, she says, changed both her way of thinking and the trajectory of her life.

“My first women’s studies class was a big unlock for me in my life, because [then] I had a framework around things I’d felt but I didn’t know. I didn’t know that hypersexualization was a thing, and that only seeing women as body parts dehumanized them," she says. "I had language to describe how I felt—and, in some ways, places to place blame. I was able then to look at institutions and societal beliefs and cultural pressures. I could understand it bigger than just, ‘Why do I not like my body?’ and ‘Why don’t I feel like I’m pretty enough?’”

Weiner had struggled with disordered eating and low self-esteem as a teen and throughout college, but found support—and a wealth of heartbreaking stories—in a campus support group. In her senior year, she helped to create a play, Body Loathing, Body Love, about her eating disorder battle. Snippets of the play and the discussion with students that followed it were aired on CNN.

In attendance that night was Ken Smith ’95 Bus, who’d met Weiner in a women’s studies media class in the fall of ’93 and remembers being “captivated” by her intellect and her initiative. Her example led Smith to join the LGBSA (Lesbian, Gay and Bisexual Student Alliance) and become a student leader, realizing that he had a voice and a responsibility to raise it when he saw injustice. Together the lifelong friends led various protests and movements on campus—including a “kiss-in” on Valentine’s Day, when heterosexual and same-sex couples surrounded the Willard Preacher outside Willard Building for a little “love is love” PDA.

But Weiner’s biggest college protest came in the spring of ’95, when the show MTV News: Unfiltered sent cameras for her to film her protest of the Mifflin Mob, which had morphed over the years from a few nude Mifflin Streakers into a horde of hundreds of clothed men swarming outside women’s dormitories yelling for the female residents to flash the crowd. In the days leading up to their well-publicized protest, Weiner and her friends faced threats of violence. On the night the mob was supposed to happen, they led a candlelight vigil outside the women’s dorms, holding painted signs and MTV’s cameras. The mob never materialized, and Weiner got her first tastes of both victory and celebrity: She was thanked by many women who’d felt powerless to the harassment, and her Mifflin Mob segment aired often on MTV that spring and summer. The clip can still be found online.

Public speaking opportunities started coming her way thanks to her CNN and MTV appearances, and at 21, Weiner formed her own traveling repertory company that performed skits she wrote about social issues—AIDS, teen pregnancy, date rape, eating disorders, homophobia, mass shootings—and then moderated discussions. The group traveled the country for six years, facing everything from apathy to scrutiny to gratitude. Reacting to the mood of the audience, pivoting to a new topic, and asking questions when she felt their message wasn’t landing all helped the young professional hone skills she’d eventually use in the boardrooms of powerhouses like Disney and Dove.

“Improvisation is still the key principle for me,” she says. “Improv for me is ‘Yes, and.’ It’s accepting what’s there and adding to it. So when I come into a company and they have terrible advertising, if I were to start off by saying, ‘You know, your advertising sucks,’ that’s a scene ender. But if I come in to say, ‘Your advertising’s missed the mark, and tell me how you feel about that, and tell me what you hope to get out of this,’ it’s that ‘and’ part that has opened doors for me with people who have been mostly closed to having critique come in.”

Two decades after she was performing for small-town community groups, often crashing with sponsors to save money, Weiner steps onto Brentwood School’s posh campus on a sunny Saturday as the keynote speaker with an entourage of nine. She’s wearing combat boots and black pants whose holes reveal fishnet stockings; the rock-star vibe is glammed up with a shimmery blouse and glittering necklace she’s been worried might get in the way of her mic. In a room upstairs, her three-man camera crew is setting up for the new project that the entrepreneur is excited to unveil.

But first, the keynote. She walks onstage after her hosts gush through a list of career highlights: Weiner worked with the White House Council on Women and Girls under the Obama Administration; she is Dove’s global self-esteem ambassador, working on its revolutionary Campaign for Real Beauty; she helped Barbie evolve to new body sizes, skin tones, eye colors, and hair styles and textures.

She steps up to the podium and immediately draws laughs from the auditorium full of teen girls by flashing pictures of her teenage self on the giant screens that flank the stage. Then she opens her pre-college journal. “Who am I? What will I become?” she reads aloud to a silent, nodding crowd. “What if I don’t reach all of my dreams and goals? Or, worse, what if I do?”

Weiner’s ability to relate to an audience 30 years her junior is a product of never allowing herself to grow out of touch with what girls and young women are facing, says Diane Reichenberger, vice president of global strategy/U.S. consumer products for Mattel, who has known Weiner since the early 2000s. Then-CEO of Dualstar Entertainment Group, Reichenberger hired Weiner to write an advice column on Ashley and Mary-Kate Olsen’s website after hearing her speak at a What Kids Want marketing conference. Weiner’s deft handling of teenagers’ questions about bullying, body image, and more impressed Reichenberger; when she heard Dove was looking for a strategist to help with its new Global Self-Esteem Campaign, she recommended Weiner.

Dove’s global research had found that only 2 percent of women self-identified as beautiful, and the company was interested in trying to change that. As an adviser for the campaign, Weiner suggested they find out what the other 98 percent needed to change their minds. But when they asked that question, the answer was overwhelmingly the same: It’s too late for me; focus on my daughter, so she doesn’t grow up thinking this way.

“That was such an amazing pivot, because I think it was when the brand realized, wow, we not only have really interesting insight and information, we have a responsibility to do something if we say we care about this consumer,” she says. Dove had no products to sell to young girls; they were not the soap company’s target market. But their moms were.

Dove introduced its Global Self Esteem Fund in 2006 with a much-talked-about Super Bowl XL ad, which featured portraits of girls overlaid with messages like “hates her freckles,” “thinks she’s fat” and “wishes she were blonde.” The spot, which Weiner had a hand in, laid out the mission of the company’s Campaign for Real Beauty: “Let’s change their minds.”

In the 16 years Weiner has worked with Dove, the brand has turned the phrase “real beauty” into a widely understood ideal, and has reached more than 60 million girls worldwide with its free self-esteem curriculum, which she helped to create. In the process, Weiner found a new niche for her entrepreneurial skills and her social activism, realizing that brands like Dove offer her a huge opportunity to affect positive external messaging and internal change. Having a seat at the table during decision-making on products and marketing meant she could make sure whoever or whatever was missing from a campaign had an advocate in the room.

“I saw the power in advertising and the power in brands to change the way you talk to people. And what I think is now happening with my clients is, how do you engage people by making them feel whole and not incomplete? How can you still sell the product if you don’t play with insecurity? There’s a trick to that too, because now brands can tend to over-rotate and just lay on a lot of platitudes and ‘go girl’ messaging,” she says of what she calls SFSN: Sounds Fabulous, Signifies Nothing. “[Brands] hold a really big space. They have a lot of money. They occupy a lot of real estate around us. So I think that’s what’s alluring to me:  How do we work with such a powerful force to try to do better?”

The median age of the girls attending the Young Women’s Conference is 15, which means they were about 7 when Brave hit theaters, introducing a new kind of Disney princess in Merida—athletic, headstrong, courageous—than many of the princesses their moms remember. These teens don’t realize the woman speaking to them now had a hand in that part of their childhoods.

In the early 2000s when Disney was rebranding what a princess needed to be for the next generation of girls, Weiner advised them on both character and packaging. The princesses that have come after that shift—Merida, Anna, Elsa, and Moana—have had a good bit more agency than many of their predecessors. “I think for us, too, it was about the product and how the princesses show up on the product. Are they posing for some audience, or are they in action poses based on their story?” she says. “That was something we helped them with: How do you show a girl living her life, not waiting to be looked at?”

In 2017 Weiner teamed up with Aerie, an American Eagle offshoot brand of intimate apparel for girls and young women, ages 15-30. Aerie had made a name for itself by not using any digital manipulation of the models in its ads. Stacey McCormick, senior vice president of marketing for Aerie, says the idea of lingerie had always been viewed through a male lens, but they’d learned their customers just wanted to feel good about themselves in their lingerie, not to be aspiring to a certain aesthetic for someone else. And that meant showing the clothes in bodies as they really are.

Weiner helped them take that one step further in 2018, when the brand launched an ad campaign using 57 real Aerie customers wearing its apparel. Bodies with all different sizes, skin tones, conditions, and illnesses were shown, with no retouching. The campaign went viral. “We learned at that point in time how important representation was, and inclusion was,” McCormick says.

Seeing how her advice translates in the market is gratifying, but much of Weiner’s work with brands isn’t seen—in the short term, anyway—on store shelves or social media. She leads internal workshops and brings in diverse speakers for intimate, intense conversations about sensitive issues with company leaders. McCormick brought her in to speak to Aerie’s executive team about the importance of the issues that were playing out in their advertising, and Weiner has facilitated workshops at Aerie headquarters on issues of diversity and inclusion as well. “She’s touched a lot of things here,” McCormick says.

Weiner gets excited about the chance to make changes to systems that might lead to bigger shifts, both for a company’s bottom line and for individuals within that company.

“I think we have to live the same messages we put out,” she says, admitting that many of the brands she’s worked with still lack a healthy diversity at their top management levels, which could suggest they haven’t completely bought into what they’re putting out. At least, not yet. “Large legacy brands—a Mattel, a Disney, a Dove—who have been around for almost 100 years, they have to change with the times. And I find that to be really exciting, because we can change teams, and we can change the future trajectory of that business.”

Kim Culmone has been on the Barbie team at Mattel for 20 years. The iconic doll had always been about inspiring little girls to imagine all the things they could grow up to be, but its feminist bent had gotten lost beneath the enduring image most had of Barbie: white, blonde, ultra-thin. Years ago, Culmone wanted Barbie to become the face of girl empowerment, with the brand offering new resources and support to enable girls to truly reach for their dreams. Weiner advised against it.

“Jess said, ‘You might not be ready for that, until you do the work that makes you believable in that space,’” Culmone remembers. So the Barbie team did the work, launching three new body types (in addition to the original), seven new skin tones, 22 hair styles, and 24 eye colors in early 2016. Weiner partnered with the team during the top-secret project, getting an education on product development, manufacturing and distribution challenges. Once the prototypes had been created, Weiner brought in some outsiders to meet with the design team and offer their honest feedback. Culmone, who had so much invested in the changes, was a nervous wreck, in part because of how much she respects Weiner’s opinion. Though a long discussion ensued regarding the length of the doll’s skirt, the general feedback was overwhelmingly positive. And Weiner got the thrill of knowing little girls like her would finally see a Barbie with a curvy body, brown skin, and curly hair, something she didn’t have growing up. “That would be validating, that I exist,” she says.

Mattel’s Fashionistas doll line has continued to diversify its Barbies in the ensuing years. But even more exciting for both Weiner and Culmone has been Barbie launching The Dream Gap Project, targeting the puzzling fact gleaned from research showing that starting at age 5, girls begin to think they are not as smart as boys. In an effort backed by Mattel, researchers from NYU and UCLA’s Center for Scholars and Storytellers are studying the Dream Gap and, with Weiner’s assistance, created a curriculum for elementary-level teachers and parents designed to help close the gap. The curriculum encourages intentionality regarding gender representation in young children’s lives: Do the majority of stories you read to your kids have male protagonists? Are there female heroes depicted on your classroom walls? It was piloted in a Los Angeles elementary school last year, with promising results, Weiner says.

“I get excited about [different-looking] Barbies being in the hands of people,” Weiner says, “but I get more excited about helping to shift an internal mindset in the organization at Mattel that values the multidimensionality of girls.”

As soon as Weiner finishes her conference keynote speech, she heads upstairs with the two women who’ve just been on stage with her: fencer Ibtihaj Muhammad, the first American to earn an Olympic medal while wearing a hijab; and Iskra Lawrence, an international model and AerieREAL Role Model who’s garnered 4.5 million followers on Instagram in part by refusing to be retouched in her photos. They enter the room Weiner’s crew has been setting up, and all three take a seat. On the table in front of them are three microphones and a letter board declaring We Are All Going to Die Anyway—the name of Weiner’s brand-new podcast. The team is silenced, cameras roll, and the podcast begins taping its first episode.

“I wanted to talk to people I admire,” Weiner tells her first guests, explaining that the aim of the podcast is to “love a little more, dig a little deeper, and learn something about ourselves.”

Based on the macabre title, the podcast might seem like a sharp departure from the career she’s been steadily building for 25 years, championing the promise and potential of young lives. But Weiner says it’s not so much a pivot as it is a honing in on the true heart of her life’s work: That judging someone’s life by how they look—judging our own lives by how we look—is the true tragedy. That real beauty is found in authenticity, vulnerability, and spending the time you have doing what you love.

She’s come to that perspective by way of personal loss, having spent seven weeks with a dying friend and her family a couple years ago, an experience she says profoundly changed her and her husband, Felipe. And then there’s the professional fatigue. By 2019, her Talk to Jess consulting business had stretched to 15 employees in order to handle nearly a dozen brand partnerships, plus varied speaking engagements and other work. She was making more money than ever but wasn’t feeling fulfilled, or healthy.

“I just lost sight of the shore,” she says, admitting to having succumbed to the rise-and-grind mentality of entrepreneurship and the hustle worship of Hollywood. “It felt like I was doing a lot and I wasn’t fully doing it with a grounded intentionality and a healthy dose of self-preservation.” So she streamlined her business from 10 brand partnerships to three, and from 15 employees to six. She took stock of what fuels her—creativity, curiosity, purpose—and carved out spaces in her professional life for them. She turned her conference room into a production studio, hired a camera crew, and finally named what she really wanted to talk about: How death’s inevitability should give us a real urgency about living.

“It almost feels like I’m more full circle back to the person I was becoming at Penn State than the last 20 years of Hollywood,” says the reinvigorated theatre grad, happy to be creating her own content again.

About 50 minutes into their podcast taping, Muhammad tells Weiner that she lost a sister recently, a death that devastated her. Weiner tears up and nods; she knows that devastation. “It taught me about the opportunity to love the people around you so much more deeply and intentionally,” the athlete says. Her sister left behind a daughter who just turned 4, Muhammad says, a little girl who looks so much like her mother and has given the grieving aunt a new sense of purpose. “It’s an opportunity to create a better world for her,” she says.

Weiner smiles and nods again; she knows that feeling too.