In 2019, after more than a decade scaling the heights of product management in Silicon Valley, Lisa Kostova (MBA 2009) decided to take on a different kind of climb. Over a sabbatical year, Kostova trained for and summited Denali, which, at 20,310 feet, is the tallest peak in North America—and a challenge that experienced mountaineers say is greater even than Mount Everest.

“It was the biggest, most vast, most intimidating mountain I had ever beheld in my life,” Kostova says, recalling the first time she set eyes on Denali. “I knew I wanted to climb it, and it became an obsession.” Sitting just below the Arctic Circle in Alaska, Denali is protected as part of a national park, which means the sort of semi-permanent infrastructure that aids expeditions elsewhere is not permitted, and climbers have to carry all their own gear. A successful Denali ascent thus relies on an individual’s training and fortitude in a hostile environment. And only ten percent of those who make it to Denali’s summit are women.

“It’s much like tech!” Kostova says. And it proved a ready-made metaphor for the next phase of her career. In 2020, Kostova founded CareerClimb, an executive development firm that focuses on helping mid-career women in the technology industry ascend to the next level.

When Kostova graduated from HBS, she believed that sexism was largely a relic of previous generations. But it didn’t take long for her to recognize that women faced a steeper slope when it came to career advancement in a field still dominated by men.

Despite companies’ ongoing efforts to diversify, women make up fewer than a quarter of US tech workers. Meanwhile, women in technical roles are half as likely as men to be promoted to manager—and their path to the top gets even narrower from there. Thus outnumbered, women can find themselves at odds with tech’s “cowboy culture,” Kostova says. She recalls the immature antics of some of the young male engineers she worked with in Silicon Valley, including at the game-developer Zynga, where she rose to become lead product manager between 2009 and 2012, before taking a job as Vice President of Product at Bright.com (which was later acquired by LinkedIn).

Changing tech’s culture will be necessary if the industry is to take full advantage of women’s talents, but that means changing who’s at the top. One way to achieve that, Kostova believes, is by helping individual women forge their own paths to leadership positions. “Everybody talks about the reasons women drop out of the workplace, about how difficult it is,” Kostova says, returning to the metaphor of Denali—which is also CareerClimb’s logo. “If you just pay attention to people who turned around, who got stuck, who never made it, you are never going to establish a blueprint or roadmap to actually summiting. Let’s look at the successful examples. What worked for them?”

Over the past three years, CareerClimb has coached more than 100 women, helping them in one-on-one sessions to explore career goals and examine the factors that may be holding them back, among them perfectionism (“We have an epidemic,” Kostova says) and self-sabotaging behaviors that her clients often struggle to recognize in themselves. Kostova also connects them to one another, building a community of women who can make “summit attempts” together. So far, her clients have secured multiple promotions and a collective $1.6 million in salary increases.

CareerClimb’s own next step is to use artificial intelligence to reverse-engineer successful paths, by isolating the most likely drivers of success in a large collection of career-trajectory data. The company is still in its bootstrap stage, Kostova says, and she has found herself considering principles she learned in her second-year entrepreneurship class at HBS, taught by the now-retired Professor Joseph B. Lassiter.

“It’s understanding how startups are different,” she says, recalling a slide Lassiter used of a Central American reptile known as the Jesus lizard—so called because it skims the surface of a pond so quickly that it looks like it’s walking on water. “I still have it etched in my mind. It was like, ‘This is your cash flow. As a startup, you have to be like this lizard.”

It’s also a reminder of the need to believe in and rely on yourself—whether you’re building a startup, aiming at the C-suite, or climbing Denali.

“Yes, it is unfair,” Kostova tells her clients of the tech world. “And now what are you going to do about it?”

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