“Hone your strengths and turn them into superpowers.” This is the advice that Annie Pearl gave a ballroom of over 500 women as she accepted her award for the SF Business Times 2019 Most Influential Women in Bay Area Business. As the SVP of Product & Design at Glassdoor, Pearl has certainly followed her own advice and empowered other women in tech to do the same. But it was her signature brand of humor — and dedication to Glassdoor — that caused the entire room to erupt into laughter.”
“And if you happen to work for a [bad boss], leave a review on Glassdoor.”
It’s this commitment to mentoring women and workplace transparency that has allowed Pearl to rise the ranks of Glassdoor to be one of the leading women at the nearly 11-year-old company.
“As a member of the Product team at Glassdoor, we have the privilege of being able to help job seekers around the world navigate this decision and find a job and company they love. It is this mission that makes the work we do every day so valuable.”
We caught up with Pearl ahead of her big awards night to talk servant leadership, the future of HR tech and what it means to be a woman with influence.
Glassdoor: How does it feel to be named one of the most influential women in Bay Area business?
Annie Pearl: I am extremely honored to receive this award and humbled to accept it alongside an impressive group of other influential women in Bay Area business. I’m particularly proud to accept this award on behalf of the Product and Design team as well as the rest of the executive leadership team at Glassdoor. I’m grateful for the recognition this brings to the work we do every day to help job seekers and employers around the world.
Glassdoor: Not only is this is a significant acknowledgment of your work but also of the work that you’ve done at Glassdoor as an SVP. How has your time and contributions at Glassdoor led up to this moment?
Annie Pearl: I have the incredible opportunity through my work as the SVP of Product and Design at Glassdoor to help over 60 million job seekers who use our product each month to find a job and company they love as well as help employers around the globe recruit high quality, informed candidates.
Through this work, we are able to provide job seekers with transparency and guidance as they evaluate whether a company will be a good fit for them, prepare for an upcoming interview, or negotiate a higher salary. These decisions are some of the most impactful decisions we make that affect our day-to-day lives and livelihood. In parallel, hiring qualified candidates who will thrive at a company is one of the most impactful decisions employers make to build successful organizations.
It is this real-life impact of this work we do on the Product and Design team that I am most proud of and has led to this moment.
Glassdoor: Take us back a bit to the journey that brought you here. How did you come to be SVP of Product and Design at Glassdoor?
Annie Pearl: I’m a Bay Area native who migrated to Southern California for college at Claremont McKenna and then came back up north to Santa Clara for law school. While I was in law school, I worked at a boutique management consulting firm who specialized in working with startups helping them scale during times of rapid growth. Through this experience, I became fascinated with technology and caught the entrepreneurial bug that led me to join the founding team of a financial services startup in 2009 after graduating from law school and passing the California bar.
It was at our startup where I started my career in product management and learned all about building a product from the ground up, finding product-market fit, and the power of focus.
After four years of leading Product and Design at our startup, I had the opportunity to join the Product organization at Box in 2012, where I was exposed to a new phase of a companies growth as we scaled through our IPO in 2015 and I learned all about how to evolve a product to meet the needs of larger and larger customers, how to effectively grow a product organization, and create new products for our Enterprise customers.
In 2016, I joined Glassdoor where I now lead Product and Design. Over the past 2.5 years, I have been able to apply the learnings from both my startup experience and at Box to help grow and scale our product, team, and company through our acquisition last year by Recruit Holdings.
Glassdoor: What makes you excited to be a woman in tech today?
Annie Pearl: What makes me the most inspired to be a woman in tech today is the pace at which women are founding and launching tech companies, becoming partners at Venture Capital firms deploying capital towards women-led startups, and holding executive leadership positions at tech companies.
As I think about women starting their careers out today, I’m excited by the opportunities that these young women will have and for the confidence, I hope they will feel, to pursue a career in tech because they have women role models to look up to across the whole tech ecosystem.
We still have a long way to go in terms of closing the gender pay gap and continuing to open up doors for women looking to enter into tech as well as hold leadership positions at tech companies but there is an incredible amount of momentum here and I’m optimistic as to the impact this will have on bringing more gender diversity to the whole ecosystem.
Glassdoor: You have an amazing team of product leaders, designers and extremely talented women in your organization. How has leading a dynamic team of men and women shaped your leadership style?
Annie Pearl: I’m a big believer in servant leadership and view the most important aspects of my role as attracting and hiring a diverse group of highly talented product and design thinkers, setting the north star vision for where we need to go, and then focusing my energy on doing all I can to support the team in getting there.
As part of this style, I look to the dynamic team of men and women in my organization to bring in a diverse set of perspectives, opinions, and experiences to define the strategy and path to achieving this north star vision. I focus on empowering the team to think big, bring in bold ideas, and push the envelope. My hope is that through this style of leadership I am able to foster a culture of innovation through diverse thinking.
Glassdoor: You’re hiring for product managers and innovators from SF to Chicago. Why should job seekers apply to Glassdoor now?
Annie Pearl: Deciding where you go to work every day is one of the most important decisions we make in life. After all, the majority of people spend more time at work than they get to spend with their families and friends.
As a member of the Product team at Glassdoor, we have the privilege of being able to help job seekers around the world navigate this decision and find a job and company they love. It is this mission that makes the work we do every day so valuable and why joining the Product and Design team leads to meaningful work.
Right now, we are working on some very exciting new products, expanding Internationally, and scaling our Product and Design org across the U.S. If you’re looking for an opportunity to learn, grow, and make a big impact, we’d encourage you to apply!
Glassdoor: Lastly, what advice would you give women in tech eyeing an SVP title? Any advice to women job applicants or women in tech for success?
Annie Pearl: I would encourage women in tech looking to grow in their careers to identify their strengths and focus more of their time and energy on how they can hone their strengths to turn them into superpowers and less energy on improving their areas of weakness.
We all have areas of growth we shouldn’t ignore but I believe you can drive a step function change in career growth and effectiveness through figuring out how to best leverage your strengths to your advantage.
I’d also encourage job applicants or women in tech to optimize more for growth and learning when taking a new role. By taking the opportunities that are going to expose you to new skills and push you out of your comfort zone, you will open up new doors down the road you might not have anticipated or didn’t even know existed. I’m a Lawyer turned product leader and I attribute much of this to being curious, looking for opportunities to learn, and not thinking about my career as a linear line but more of a jungle gym.
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