http://fortune.com/2017/09/22/hp-hpe-meg-whitman/
Meg Whitman licks her goggles, steps up to the ledge, places one hand on the concrete, and hurls herself, pencil-straight, into the turquoise-blue water. She’s off in a brisk freestyle crawl—“Race pace!” yells a coach—covering close to half the pool before coming up for air. It’s 7 a.m. at the outdoor community pool in Menlo Park, Calif., where the CEO has been swimming almost every morning since January 2011—just after she lost the race for California governor, just a few months before she took over Hewlett-Packard at the darkest point in its history. She’s not just doing laps; it’s a “boot camp–ish” routine of breaststrokes and freestyle sprints and flip turns, and Whitman, in lane six of the 10-lane pool, is at the center of it all.
“I needed something to take my mind off losing,” she says of her decision to jump back in after three decades away from competitive swimming. By the time she emerges after an hour, glistening and flushed, she’s beaming; standing beside the water in a black, pool-worn one-piece bathing suit, she puts her hands on her hips and turns her face to the morning sun. It’s the ultimate power pose: This is what winning looks like.
The 61-year-old Whitman hasn’t exactly won yet. She holds a unique distinction, not just as a woman running a Fortune 500 company but as the only woman to have run more than one—first eBay, now Hewlett Packard Enterprise. (Irene Rosenfeld, the outgoing CEO at Mondelez, ran a predecessor of the same company, Kraft.) Yet today, about five years after she laid out a five-year plan to rescue HP, her success there is far from assured.
Nearly two years ago, Whitman led Hewlett-Packard through the biggest corporate breakup by revenue in history, cleaving the $103 billion company into two: HP Inc. (hpq, +0.86%), where she recently stepped down as chairman, and Hewlett Packard Enterprise (hpe, +3.41%), where she remains CEO. At HPE, which sells servers, cloud-computing software, and “Internet of things” networking systems for businesses, Whitman has continued slicing off divisions and coaxed profits into rising. But HPE’s revenue has shrunk to an estimated $33 billion this year, and she’s not positive she can get it to grow again. Meanwhile, HP Inc., the stodgier printer- and PC-maker, has been posting near-double-digit sales growth and upstaging HPE’s stock.
“I might be the only CEO in America who wants to run a smaller company,” Whitman likes to say. But it’s not clear how much longer she’ll do that. In June she promoted Antonio Neri, head of HPE’s enterprise group, to president, positioning him as her likely successor. In August she was a top contender to replace Travis Kalanick as CEO of Uber, in which Whitman was an early investor—a job that could have teed her up to eventually lead an unprecedented third Fortune 500 company. (The ride-sharing giant went with Dara Khosrowshahi.) And recently she’s been leading on a bigger stage. A lifelong Republican, Whitman switched her support to Hillary Clinton three months before last year’s election—she was the only Fortune Most Powerful Woman to publicly campaign for a nominee—stoking speculation that the former gubernatorial candidate would reenter the political arena. “Frankly, I think a leader of every organization now needs to stand up and be counted,” Whitman says. “History will judge.”
Whitman is still most celebrated for her decade at eBay, which she grew from oddball dotcom startup to e-commerce powerhouse. But the reputation she earned there is the opposite of who she’s become: a turnaround CEO, the grownup who could clean up HP’s mess—and why not Uber’s too? The cynic’s view is that she’s a one-hit wonder, boxed in at a company whose glory days are long behind it. Now, confidants think the intensely competitive Whitman wants another chance to solidify her legacy. Says Neri, “Meg does not like to lose, trust me; she does not like to lose.”