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Glassdoor CPO Annie Pearl: “Why Overcommunication is critical”

Overcommunication is critical. As a leader, your number one job after setting the vision is to evangelize it so everyone knows where you’re going. Whenever you feel like you might be overcommunicating, continue to do it even more. Now as Chief Product Officer, I make sure everyone across the company is clear on what we’re […]

Overcommunication is critical. As a leader, your number one job after setting the vision is to evangelize it so everyone knows where you’re going. Whenever you feel like you might be overcommunicating, continue to do it even more. Now as Chief Product Officer, I make sure everyone across the company is clear on what we’re doing from a product perspective and perhaps more importantly, why we’re doing it.


As a part of my series about strong female leaders, I had the pleasure of interviewing, Annie Pearl. Annie is Glassdoor’s chief product officer, responsible for the company’s product vision and user experience for job seekers and employers around the world. Before Glassdoor, Annie led enterprise product teams at Box, including before and after its 2015 IPO. She was also the vice president of product and one of the founding members of Xpert Financial, which helped investors trade private company securities. Annie has also consulted and advised several rapid growth start-ups. She was honored as one of the Most Influential Women in Bay Area Business in 2019 by the San Francisco Business Times. Annie holds a J.D. from Santa Clara University School of Law and earned a bachelor’s degree from Claremont McKenna College. She is a member of The State Bar of California.


Thank you so much for doing this with us! Can you tell us a story about what brought you to this specific career path?

My career journey has not been a straight path, but one that resembles more of a jungle gym, with constant learning along the way. I went to law school and passed the California bar exam, but quickly became much more interested in technology, building companies and developing products. I soon found myself consulting for startups that were either early stage or going through rapid phases of growth.

In 2009, I joined the founding team of a startup whose vision was to create a stock market for private companies, which led me to become involved in and lead product management. I realized I was a lot more interested in building products and seeing how my ideas could come to life to solve real problems for people. I think about that startup experience as building the muscle around how to go from 0 to 1 and find product-market fit, because at that point, you’re building the company from the ground up.

After about four years, I went over to Box. At the time, Box was in a different phase of growth, because the company had found product-market fit and was entirely focused on product scalability. I was able to learn a ton about scaling products to meet the needs of larger customers, building new products and revenue streams, and scaling product teams.

After four years at Box, I decided to join Glassdoor because I love the company’s mission to help people find a job they love. After a year and a half, I got the incredible opportunity to lead all of Glassdoor’s product and design globally.

Can you share the most interesting story that happened to you since you began leading your company?

I’ve had many incredible experiences during my time at Glassdoor, but I’d have to say our acquisition by Recruit Holdings in 2018 was definitely an interesting learning moment for me. As a leader in product, it presented this fun challenge and shift of balancing two business needs. On one end, we needed to continue to support Glassdoor’s core business and continue to iterate on our successful products and offerings. On the other, we needed to collaborate with our new parent company and begin to make bigger, more innovative bets. Playing this balancing act has helped us refine and design our vision for the next decade at Glassdoor.

It was also interesting to see that unlike many acquisitions out there, Glassdoor was able to maintain our brand identity and culture.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

When I was co-leading a small start-up, Xpert Financial, we all made the classic mistake of getting too eager and doing far too many things at the same time, which prevented us from focusing on our strengths. The biggest lesson I took away is the power of focus: do one thing well, and then build from there. The nice thing about that lesson is it isn’t just applicable to startups. I think it’s just as important when you think about scale and working with a company of our size, where success often comes more from what you don’t do, than what you do.

What do you think makes your company stand out? Can you share a story?

What makes us standout is the mission and product itself, to increase workplace transparency in hopes of helping people everywhere find a job and company they love.

Because of the power of our mission and what we offer, I can’t really get away from Glassdoor if I tried, which isn’t a bad thing! For example, whenever I fly, people notice the Glassdoor sticker on my laptop and they approach me to tell me how much they love the service. A flight attendant once told me she used the platform to find the right airline to work for, another person on a flight told me they successfully negotiated a higher salary, and yet another person told me they dodged a bullet by not taking a job at a firm with concerning reviews on Glassdoor. It’s always amazing and humbling to see how our work and our platform has actually helped people around one of the most important decisions they have to make.

Are you working on any exciting new projects now? How do you think that will help people?

Yes, many. At the core, we’re continuing to build on our mission to help people everywhere find a job and company they love. From a product perspective, we’re investing in deeply understanding job seeker behaviors and motivations to provide more personalized services that match them with the right job opportunities, making sure they’re prepared for a successful interview/salary negotiation and connecting them with the right employers. We aspire to be a sort of personal career coach for job seekers.

What advice would you give to other female leaders to help their team to thrive?

I’m a big believer in knowing your strengths and turning them into super powers, instead of focusing all your energy on the areas you need to develop.

I’ve found that this approach leads to better leaders because it creates a culture of inclusion where teams feel that their unique strengths are celebrated, instead of a culture where everyone needs to do things the same way, and if you’re not doing it, you need to get “better.” Women, in particular, are prone to spending more time focusing on our weaknesses, but that doesn’t help you get further in your career. Embracing your strengths and turning them into super powers does.

What advice would you give to other female leaders about the best way to manage a large team?

I really think about my role through the lens of servant leadership and recommend this approach to others. Through that lens, I see my job as setting a clear vision and strategy for where we need to go and then doing everything in my power to make my team successful in getting us there. As you scale and your team grows, you can’t be as close to all the day to day decisions, empowering your team is a much more critical part of the job. Some of the best ideas I’ve seen have come from teams that feel empowered and are on the ground listening to our community, engaging in the data, and understanding pain points that our users may have. Empowering your team to come up with bold ideas, and creating a culture where failures are celebrated can lead to people feeling more confident and to working even closer together.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I can’t really say there was just one person. At every phase in my career I can point to someone, whether it’s a boss who took a chance on me, a startup advisor who coached me, an executive who became my champion, and so many people in between, who helped me get through a challenge, or open a door. Along the way, these mentors have joined my personal board of directors, and to this day, they continue to be people I go to for advice.

How have you used your success to bring goodness to the world?

One reason why I work in product at Glassdoor is because I truly believe that my job brings goodness to the world. I love knowing that the work I do everyday has an impact on millions of people who are trying to become more informed on a critical life decision they need to make — where to go to work. Leading product, I have the opportunity to shape the way in which Glassdoor is designed so that it’s easiest to navigate by users who are making important job and work decisions.

In addition, outside of my day-to-day role in product, I spend a lot of time as a mentor, trying to give back what so many of my mentors have given to me. For instance, I mentor young women entrepreneurs at an accelerator, hoping to help guide them in their own careers and professional decisions. Internally at Glassdoor, I’m a sponsor of our Women in Glassdoor employee resource group, whose mission is to cultivate an inclusive environment for women to advance their skills and leadership potential. We focus on networking, skills development and training, and personal and professional development.

What are your “5 Leadership Lessons I Learned From My Experience” and why. (Please share a story or example for each.)

  1. Resilience is powerful. We can learn a lot more from our failures than successes. We should take them as gifts and opportunities to grow as leaders. At Xpert Financial, we had to fold, which was really hard to stomach at the time. I started to compile a list of everything I learned over the course of those four years, and I continue to reference that list today. There were a lot of positives that came from that experience because I was able to learn from them and evolve in my future roles.
  2. Be authentic. When people bring their full selves and experience to work, it contributes to better productivity and fosters innovation. Create a culture where diversity is celebrated, and people feel like they can be their true selves. This creates a more innovative team that drives better results. At Box, I hired a product team with people from diverse backgrounds (i.e. customer success, finance, engineering, etc). This team created a first-of-its-kind product to solve a problem in a new way. Leaders should be authentic by bringing their vulnerable self to work. People want to be led by real people they can relate to. In every stage of my career, I’ve been the most inspired by those types of leaders.
  3. Overcommunication is critical. As a leader, your number one job after setting the vision is to evangelize it so everyone knows where you’re going. Whenever you feel like you might be overcommunicating, continue to do it even more. Now as Chief Product Officer, I make sure everyone across the company is clear on what we’re doing from a product perspective and perhaps more importantly, why we’re doing it.
  4. Assume a role of servant leadership. I’ve found this to be a really successful way to lead and inspire teams. Empowered teams are effective teams.
  5. Focus on your strengths. Earlier in my career, I focused all my energy on areas I perceived as weaknesses and made incremental improvements in my effectiveness. At Box, I shifted my focus to harnessing my strengths in creating a compelling product vision, rallying people around it and leading them through making it come to life. This drove a step change in my performance and enabled me to create new products and more efficient processes there.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

As a new mom, I feel pretty passionate about finding more ways to better support women who choose to become mothers and also want a career. There’s a lot of research that shows the gaps between men and women in pay and opportunities and unfortunately, that these gaps only widen as women take time off to have children. And, if you have several children, it compounds over time. This needs to change. I’d love to figure out how to better support women who want to be mothers, but also care about their careers. Companies should do more to help women who are transitioning back into the workforce and work to remove any stigmas and barriers.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

‘Fake it till you make it,’ though keep in mind this comes with some context. Everyone — even the most powerful CEOs — at some point will encounter something that they’ve never done or seen before. What’s made me successful during those situations is not shying away from them because they scare me, but approaching them as learning opportunities, and with confidence as if I’ve done it before. I’ve found that more often than not, you aren’t faking anything — if you’ve been asked to do it, you’ve actually made it.

Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them 🙂

Serena Williams. Not only has she smashed record after record in the male-dominated world of professional tennis, but she has also expanded her sphere of influence in another historically male-dominated industry — venture capital. It’s amazing and inspiring how she has also now started a firm that invests in female and minority-owned companies. And it’s all while being a mother, too. I’d love the opportunity to connect with her about what strategies she’s used to continue to smash barriers and navigate life’s ups and downs through it all.

How can our readers connect with you on social media?

Feel free to connect with me on LinkedIn — https://www.linkedin.com/in/anniepearl/

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