Rachel Romer remembers lying on the ground on a warm August evening last year, watching as darkness descended around her. She had been sitting on her outdoor patio in Denver, where she liked to unwind from long days as the CEO of Guild, the $4.4 billion education and upskilling startup she cofounded. Suddenly, she fell. She could barely move her right arm or leg, and night was closing in.
Romer, heading up one of the world’s most valuable female-founded startups and a mother of two, had suffered a stroke at 34 years old.
The right side of Romer’s body was immobilized, but her mind was running at full speed. She lived in a close-knit neighborhood with family nearby; her ex-husband was next door with their twin girls but too far away to hear her soft cries for help. “I decided at some point to try to save some energy because I could tell I wasn’t projecting much noise,” she says.
Romer had one hope: She knew her aunt walked her dog past the house most mornings. She closed her eyes and waited for dawn.
She awoke to the sound of birds chirping and to her aunt, out for her morning walk earlier than usual. As a nurse, her aunt immediately recognized the signs of a stroke. “She was shocked that I was talking,” Romer says.
Paramedics rushed Romer to the hospital, where she would spend the next three months.
The stroke and ongoing recovery reshaped Romer’s life—and the future of her company. Guild had always tried to develop a path forward for American workers, but Romer’s ordeal forced her and her team to contend with the startup’s own future and gave them new insight into the challenges they’ve been reckoning with all along.
Nearly nine months later Romer wheels into a conference room at Guild’s Denver offices. She’s dressed for ease and comfort in a Guild sweatshirt and leggings, plus a mood-boosting bright blue manicure, as she navigates life in a wheelchair, or sometimes with a cane or walker. Her hair is close-cropped, growing back after three brain surgeries. She speaks directly and in short sentences. She has mild facial paralysis and a more monotone voice than before, but her working left hand is animated as she talks. Unlike many stroke survivors, she retained her communication skills. That was thanks to her “flipped brain,” a phenomenon in left-handed people in which speech is stored on the opposite side than it is for most—present in just 1% of the population, according to Carolyn Cronin, medical director of the Maryland Young Stroke Center.
Romer cofounded Guild nine years ago with Brittany Stich (who left in 2020) and her father, former Colorado State Sen. Chris Romer, aiming to plug holes in education and retraining systems to help workers whose jobs are being automated by technology. Romer had previously founded a community college student advisor app and worked for the 2008 Obama presidential campaign and White House.
Her interest in education started at home. One side of her family is Colorado royalty; her grandfather Roy Romer was governor. Her cousins on that side didn’t have to pay for college themselves. Some cousins on the other side took on student debt or struggled to gain skills needed for better jobs. “I had this A/B test in my family,” she explains.
Affordable, vocation-based community college should have offered a solution, but Romer soon recognized the gulf between coursework and employers’ needs. The system “hadn’t been modernized to today’s skills,” she says. Plus, many community college students struggle to study while working; in 2023, only 43% completed degrees within six years. She conceived of an organization—first a nonprofit, later a venture-backed business—that would connect the dots between higher education, employers, and the U.S.’s share of the 400 million to 800 million global workers preparing for generational workforce shifts.
Romer got a tip that Chipotle was trying to help its workers attend college but was struggling to roll out the benefit nationally. Many large employers offered college tuition reimbursement, but workers had to pay the costs upfront, so the perk often languished unused. Romer’s cold email to the fast-casual restaurant chain earned Guild its first customer. She epitomized “founder-led selling,” says venture capitalist Aileen Lee of Cowboy Ventures, an early Guild backer.
After signing its first customer, Guild quickly took off; today it counts much of the Fortune 500 as clients, including Walmart, Disney, and Target, and has raised $643 million in venture funding. Investors are drawn to Guild by the same factors that lure customers: the very immediate problem the company is solving and Romer’s persuasiveness.
Guild has long been known for upskilling cashiers and call-center staff—with 2 million members since its launch. Today it’s a marketplace that connects workers with classes ranging from GED or HVAC certification to coding boot camps and bachelor’s degrees. Guild doesn’t run those classes (although it tried to at one point); it sources them from schools. Employers pay employees’ tuition, which they see as a recruitment and retention tool. A worker studying via Guild was 2.3 times less likely to leave their employer in the past year, Guild reports. In that same time, 88% of students passed its programs, the company says.
Romer was “someone you knew was going to do something incredible in the world, but you weren’t sure exactly what.”
Now Guild is preparing for the most significant workforce transformation of the 21st century. The debut of ChatGPT expanded employers’ upskilling needs to their white-collar employees, forcing Guild to keep up. In addition to helping workers earn degrees, employers want to help them acquire targeted skills so they’re prepared when AI remakes their jobs; 30% of hours worked across the U.S. economy are expected to be automated by 2030, according to McKinsey.
Romer’s stroke and recovery are also reshaping Guild. During her hospital stay and physical therapy, she peppered health care staffers with questions about their careers. What did they want to do next? How would they pay for it? Their answers convinced her that the health care system needs a drastic educational overhaul. She took that mandate back to Guild, which first entered the sector in 2021 and has nearly doubled the number of health care organizations it worked with in the past year.
“The shortages are real,” says Guild executive Bijal Shah of the labor issues facing health care, which are caused by a combination of factors, from working conditions to the needs of aging baby boomers. “They impact someone like Rachel, and they impact this country.”
Romer won’t be the one incorporating these changes day-to-day at Guild. She permanently stepped down from the CEO role in April as she faced an uncertain recovery—regaining use of her right arm and learning to walk independently again. She remains on the board of directors, though she is still officially on leave. She was “clearheaded” about the decision, says Guild board cochair Ken Chenault, former CEO of American Express. Romer passed on the CEO title to Shah, whom Romer hired in 2018 as Romer prepared for parental leave—a bench of talent that proved critical in handling an emergency. Romer was in and out of a medical coma in the ICU for 12 days. When she would occasionally wake up, she used her fingers to spell out her daughters’ names. The first morning she woke up in the ER, she said, “Somebody call Bijal.”
It’s become second nature for Shah to check on Romer’s needs; when they sit down for a conversation in Denver in May, Shah ensures Romer is comfortable before getting started.
The pair had a collaborative relationship before Romer’s stroke. Shah became Romer’s right-hand woman—a more seasoned big-company executive from Visa and cash-back rewards platform Ibotta—to Romer’s founder profile.
The two discussed problems in the U.S. foster care system the first time they met, Shah recalls. Romer was “someone you knew was going to do something incredible in the world, but you weren’t sure exactly what,” Shah says.
Shah has held several roles at Guild, including chief product officer, chief technology and payments officer, and chief experience officer. When Romer had her stroke, Shah was on parental leave; she came back early after a difficult birth to run the firm. “This business is yours,” Romer told her at the time.
As CEO, Shah must consider another big change: whether to take Guild public. She demurs when asked about an IPO and says she’s creating “optionality” at the well-capitalized startup to “figure out what makes sense.”
Today, when Romer hears birds chirping, she recalls that morning last August on her patio. “It reminds me—another day, time to get up, get gritty, and get persistent,” she says.
It’s not that uncommon for a woman of reproductive age to have a stroke. About 15% of strokes occur in people under 50, says Cronin. Common risk factors include high blood pressure, high cholesterol, and a smoking habit. In young patients, trauma, hormone fluctuations in women, and autoimmune disease are other potential causes. Romer firmly rejects the suggestion that burnout contributed to her stroke. Her doctors dismissed that possibility, which is floated only by those who don’t know her. “I wanted to see my girls and know how they were doing the minute I was able to communicate. That’s how I felt about Guild too,” Romer says. “It’s my other child.”
In fact, she’s setting goals now, just as she did as CEO, though her objectives are simpler than before: to walk and to style her daughters’ hair for ballet.
“I feel okay about how I lived my life up until the stroke,” Romer says. “I’m trying to embrace the learnings I have and make purpose of those.”
As Romer built Guild, other female founders created their own unicorns. Guild is rare for having earned its value via education. Source: Pitchbook
1. CanvaMelanie Perkins’s Canva, an Australian graphic design and visual communications business, is the world’s most valuable startup founded and run by a woman. It’s worth $26 billion.
2. Anthropic A brother-sister duo launched the OpenAI rival that inked a $4 billion investment from Amazon. Cofounder Daniela Amodei is president of Anthropic, valued at $18.4 billion.
3. XiaohongshuThe popular Chinese social media and e-commerce platform (a.k.a. “Little Red Book”) was worth $14 billion as of mid-2023. Cofounder Miranda Qu is president.
4. DeelShuo Wang, now Deel’s chief revenue officer, cofounded the global human resources tool that helps companies hire across borders. Deel is valued at $12 billion.
5. Cityblock Health Toyin Ajayi cofounded Cityblock in 2017 and became its CEO in 2022. The health care startup, valued at $6.3 billion, aims to serve marginalized populations.
This article appears in the June/July 2024 issue of Fortune with the headline “Rachel Romer built Guild into a $4.4 billion unicorn. After Romer suffered a stroke at 34, Bijal Shah will navigate its next chapter.”
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