Kyle Leahy (MBA 2011) stepped into the CEO role of Glossier in May 2022 ready to take the brand to new heights. Since its founding in 2014, Glossier had disrupted the beauty industry, created a powerful community-driven brand, and was looking to build the business that would unlock its growth and potential. With diverse experience in hand and a deep passion for the company’s mission, Leahy is showcasing exactly why she is the right person for the job.

The Beauty of Combining Art and Science

In many ways, Leahy’s path to the Glossier CEO seat working at the intersection of art and science started in her early years. The influence of her mother, an artist, and her father, a mathematician-turned-businessman, inspired Leahy to explore both passions throughout her life. Her parents also encouraged her ambitions and were strong advocates of women’s rights, helping to propel her self-belief and excitement about future opportunities.

Kyle Leahy (MBA 2011)

In young adulthood at Georgetown University, Leahy set out to uncover where her career path would lead, double majoring in English and Math. This academic combination allowed her to use her creativity and skills in quantitative analysis, both of which she’d later use at the helm of the beauty brand.

Yet, as Leahy notes, she didn’t plan out a career in beauty. Instead, she tested out different hypotheses and followed her curiosity. Some early stops in her career included internships at Merrill Lynch and Putnam, consideration of joining Teach for America or law school, and then ultimately management consulting after college graduation. In consulting, Leahy had her first exposure to the retail industry, working primarily with clients in the retail banking and consumer sector.

“I received really great training in management consulting around working with management teams, partnering with C-Suite leaders on challenging strategic questions, financial analytics, customer strategy, and operations,” she recalled. “I also found that I loved the retail space and consumer psychology.”

Reformulating with an Advisor to Operator Pivot

After four years in consulting, Leahy came to two important realizations: she wanted to be an operator and she was craving more creativity.

“I love working with people and I really wanted to get my hands into the business,” she says. “I also wanted to tap into my creative side and work with brands that personally inspired me.” To make this career transition, Leahy made the move from New York back to her home state of Massachusetts to attend Harvard Business School.

“HBS opened up my global perspective,” said Leahy. “It allowed me to see the world through the international platform HBS provides, but also opened my way of thinking to see all the different types of career paths that there might be.” HBS also added to the rich fabric of relationships Leahy has built over the years that have helped her continue to learn and grow. “At HBS I built lifelong friendships. It was a community that exposed me to so many fascinating, smart, kind, humble, incredible people with so many different diverse backgrounds.”

It was also at HBS that Leahy learned she could utilize her skillset in strategy consulting to contribute to an iconic brand.

“I ultimately went to do my internship at Nike in the Corporate Strategy Development group and that was really life changing for me. I hadn't realized that corporate strategy at a place like Nike existed,” Leahy says. Nike was also where Leahy learned the power of building, growing, and maintaining a brand—a driving force in her career to this day.

Building Her Leadership Style

At Nike, the seed was planted for Leahy to develop her own leadership style and values. “I found this smart, talented, ambitious group of leaders at Nike who also had a very good sense of balance and sense of whole person,” says Leahy. It was a culture she could see herself within for the long term, and one that she would ultimately build in future roles as a proud professional and parent.

However, after graduation Leahy was eager to stay on the East Coast, so instead of moving to Oregon, she enthusiastically joined Cole Haan, a Nike portfolio company. The Nike-owned company provided the culture fit she enjoyed while also affording her the opportunity to learn different areas of the business within a smaller company in her corporate strategy role.

Several years later, when Cole Haan was put up for sale, Leahy was saddened to leave the Nike family, yet welcomed the opportunity for growth. “I was able to join the management team responsible for carving out Cole Haan from Nike and standing it up as an independent company, growing it, transforming it, and turning it around. I got to wear a lot of different hats,” Leahy recalls.

From there, Leahy took on the General Manager of E-Commerce role and later GM of North America position, leading thousands of employees and a billion-dollar business. During this time, she also took on new roles in her personal life, marrying her husband Mike and becoming a mom to her two children. “My family is my north star,” says Leahy. “I want to take all that I've learned and try to build a better world for them.”

Making Her Mark with Mission-Driven Work

This desire to build a better world for her children and future generations set in motion Leahy’s next career move to Glossier.

A chance encounter with Glossier founder Emily Weiss provided Leahy the opportunity to explore how she could combine her excitement for iconic consumer brands with a passion for purpose driven work. As conversations continued between the two business leaders, it was clear that Leahy would add value to the team and joined as Chief Commercial Officer. Six months later, she took the CEO reins.

Leahy was drawn to Glossier because as she describes the company, “It’s a generation defining brand that is transcendent of beauty. The company has set the bar for how brands can really drive change, not just in the brand experiences or in the way that we think about digital experiences, but also in the ways we think of using our platform for purpose.”

“The beauty industry is a $500 billion industry that's been built to make women feel that they should look a certain way or feel a certain way. We are looking to turn that on its head and give voice to the idea that feeling good about yourself isn't about looking a certain way or having a certain background or certain skin color. It's about coming as you are, and that to us is what ‘You look good’ is all about.”

Leahy is proud of the business results she and her team are driving and knows they stem from financial and strategy decisions, but also decisions the company is making around culture and values.

“We're very committed to having a modern, diverse workforce and so we're embracing and celebrating hybrid work so that we can give people the flexibility that allows those groups, particularly women and people of color, that have been excluded from the traditional working paradigm to thrive,” Leahy shares. The company also prioritizes using its platform to support underserved communities and elevate Black-owned beauty businesses.

This purpose-driven work is a motivator for Leahy as a parent and professional: she is building an iconic brand while doing her part to build a brighter future.

The Lily Pad Strategy for Career Growth

Achieving a CEO role is a goal shared by many HBS students and alumni, so we asked Leahy what advice she would share to help others on their path to the C-Suite. Her answer was not about climbing the corporate ladder, however—it was about approaching career growth like a hop from one lily pad to the next.

“One of the things that has unlocked my career has been this lily pad approach and not being so focused on one title or one destination,” Leahy shares. “There's so much pressure and stress that individuals feel to find the perfect internship or the perfect next job. But HBS students and alumni are incredibly talented and can find the connective tissue from one step to the next step. For me, it was from consulting, then to corporate strategy in consumer brands, then moving from a corporate strategy role into a GM role, and athletic apparel into accessories and then beauty. Making small, connected steps along the way has allowed me to grow and evolve my career in both intentional and often just serendipitous ways.”

With each small, connected step to the next lily pad, Leahy focused on staying “optimistic and opportunistic,” focusing on what she could learn and how she could grow. “I found that more doors have opened with the approach of being willing to raise your hand and say yes. My career has taken many paths that I would never have scripted out if I had the chance to script them out up front.”

Leahy adds that surrounding herself with talented people and within companies where she could learn and grow has also been key to her success. “For me, that has looked like entering companies that are going through phases of transformation, so whether that’s a turnaround, or scaling, or a growth phase. It’s dynamic and usually that’s where you have the opportunity to have those exponential career expansions.”

“Also, make sure you're surrounding yourself with people you admire and respect that you can learn from. Find people that complement your skill set. I've learned early on to out-hire myself—amazing people push you up and you’ll continue to get better.”