Healthcare in America is complicated in ways that make most business challenges look straightforward. There are insurance companies, hospital systems, pharmaceutical manufacturers, government regulators, employers, and somewhere in that maze of competing interests are actual human beings trying to stay healthy. Most executives approach this complexity with PowerPoint presentations and reorganization plans. Gail Boudreaux approached it like someone who had spent her entire life learning how to win when the odds weren’t in her favor.
Before she became CEO of Elevance Health, one of the nation’s largest health insurance companies serving 112 million people with 175 billion in annual revenue, Gail was dominating basketball courts. Not metaphorically dominating. Actually dominating. The kind of dominating where your records stand for decades and people still talk about your games forty years later.
The Foundation
Chicopee, Massachusetts in the late 1970s wasn’t producing many future Fortune 500 CEOs. But it produced a 6-foot-2 center who averaged 23.4 points and 20 rebounds per game, scored 1,719 career points, won two state championships, and became a Parade All-American. She also held the Massachusetts state shot-put record.
At Dartmouth, a stress fracture derailed Gail’s freshman season. She returned as a sophomore to lead Dartmouth to its first Ivy League championship with a devastated roster—eight players suited up for the championship game. They won by 17 points.
By graduation in 1982, she had become a three-time Ivy League Player of the Year—the only women’s basketball player in conference history to earn that honor three consecutive years. Dartmouth’s all-time leading scorer (1,933 points) and rebounder (1,635 rebounds). Four-time first-team All-Ivy. Two-time Academic All-American. She also won four consecutive Ivy League shot-put championships, adding discus and javelin titles.
Dartmouth has competed in varsity athletics for over 150 years. Gail is the only athlete whose jersey the college has ever honored.
The Corporate Pivot
Gail graduated from Dartmouth with honors and earned her MBA with distinction from Columbia Business School in finance and healthcare administration. She joined Aetna, spending twenty years learning how healthcare actually worked. In 2002, she became president of Blue Cross Blue Shield of Illinois, then executive vice president of Health Care Service Corporation. By 2008, she joined UnitedHealthcare as president of the commercial business.
Three years later, she was named CEO of UnitedHealthcare—45 million customers, 120 billion in revenue. She navigated the Affordable Care Act’s implementation while managing one of the most complex business operations in America. Then she stepped away to start her own healthcare consulting firm, GKB Global Health.
Taking the Helm
In November 2017, Anthem—now Elevance Health—named Gail as CEO. She inherited a traditional health insurance company in an industry facing massive disruption. Her approach reflected lessons from basketball courts: you can’t win alone, everyone has a role, and sometimes you need to completely change how you play.
Gail led Elevance’s rebrand from Anthem, signaling a shift from traditional insurance to what she calls “elevating whole health.” She restructured operations, acquired strategic businesses, and launched Carelon as the company’s services division. In 2024, Elevance launched Mosaic Health, a national primary care platform serving nearly one million consumers.
The financial results reflected systematic execution. Operating revenue grew from 170 billion in 2023 to 175 billion in 2024. The company navigated Medicaid challenges and industry-wide cost pressures while maintaining profitability. Gail authorized an eight billion increase to the stock repurchase program and raised the quarterly dividend by five percent.
Breaking the Boardroom
In 2023, Gail became the first woman elected chair of The Business Council. She serves on Target’s board and regularly ranks among the world’s most powerful women in business according to Fortune and Forbes. She received the NCAA Theodore Roosevelt Award in 2022—the association’s highest honor. The Billie Jean King Leadership Award followed in 2018. She was inducted into the New England Basketball Hall of Fame and the Academic All-America Hall of Fame.
The Playbook That Matters
When asked about navigating COVID-19 as CEO, Gail’s answer came from her playing days: “In sports you learn every game plan is fantastic until someone’s defense is better than your offense. With the pandemic, there’s no playbook.”
That’s the lesson from Gail’s career. Sports taught her that complex problems rarely have obvious solutions, teams matter more than individual brilliance, and sometimes the best strategy is to keep executing when everyone else is panicking.
She endowed Dartmouth’s women’s basketball coaching position with her family. Both her sons played college sports. The lessons she learned on the court get passed forward, because those lessons actually work.
Running a company that touches 112 million lives requires the discipline to show up every day, the humility to listen to people who know more than you about specific problems, and the conviction to make hard decisions. Gail learned those skills while averaging 21.9 points and 18.4 rebounds per game as an Academic All-American.
Healthcare is still broken in a thousand ways. But Gail’s approach—systematic, collaborative, grounded in data but driven by purpose—represents the kind of leadership the industry desperately needs. She’s not revolutionizing healthcare with grand theories. She’s making it work better for actual people, one operational improvement at a time. That’s harder than hitting a game-winning shot. But she already knew how to do hard things.
