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Career Advice From Three of Glassdoor’s Female Leaders

Glassdoor Team
Glassdoor Team | Author & Career Expert at Glassdoor | 6 Mar 2020
To celebrate International Women’s Day at Glassdoor, we’re highlighting three of our inspiring female leaders and discovering their career secrets. Read on and meet:
Annie Pearl: 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 which led me to become involved in and lead product management. I realised I was a lot more interested in building products and seeing how my ideas could come to life to solve real problems for people. After about four years, I moved to Box which was in a different phase of growth and 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.
Kate Ahlering: For me, landing in sales was a relative inevitability. Both of my parents spent their careers in sales and revenue leadership positions, so I often joke that I was born in a sales petri dish. However, my start in sales wasn’t necessarily deliberate.
During one of my first interviews post-graduation, I sat down in front of a fantastic woman who would end up being my boss for many years. At the time, I was deciding between pursuing sales or marketing. She asked if I knew the difference between the two, and I’m certain I wasn’t anywhere close to the right answer. She looked at me and said, “I think you should be in sales.” The rest is history.
Carina Cortez: My friend/mentor/former boss: Lou Sanchez. He was the hardest on me, had high expectations, and set really high goals for me. But he coached and mentored me along the way, gave me tough feedback and had my back. He took a chance on me and this really propelled my career.
Annie Pearl: 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.
Kate Ahlering: I’ve been fortunate to have a few unofficial advisors that helped build my career. For example, early on in my career, a senior executive generously agreed to have breakfast with me every couple of months. We never had a formal agenda but I came with questions, he talked about what was happening in the business, and I learned a tremendous amount from him. That small investment of time meant a great deal to me; he was very influential in the early days of my career. I still apply a lot of the lessons I learned from him today.

- Carina Cortez, Chief People Officer at Glassdoor
- Annie Pearl, Chief Product Officer at Glassdoor
- Kate Ahlering, Chief Sales Officer at Glassdoor
What Does International Women's Day Mean To You?
Carina Cortez: Did you know that International Women's Day has been in existence and celebrated since 1911? International Women's Day is an opportunity for everyone to celebrate the achievements of women and shines a light on gender parity. According to Glassdoor Economic Research, within the US, women earn 79 cents to every $1 their male counterpart earns (in the UK, it’s 82p for every £1 that men earn). When I think of 8th March, this is about the time of year a woman will have caught up to earning the equivalent of their male counterparts from the previous year. Annie Pearl: International Women's Day is an opportunity to celebrate the incredible achievements of women across the globe and also to raise awareness that there is still so much work to be done to close the gender equality gap. I believe that fostering diversity within companies and in the boardroom is a business imperative and International Women's Day is an opportunity to continue to raise awareness around the work we still need to do. Kate Ahlering: For me, International Women’s Day is about celebrating the amazing journeys of both the women I’m proud and honoured to be surrounded by on a daily basis and those throughout the world. It’s a moment to reflect on the progress we’ve made towards gender equality, while recognising there is much still to be done. I’m a big believer in the collective power and spirit of women. Today we should honour the women who have fought, suffered, and paved the way to empower the next generation.Talk Us Through Your Inspiring Career Journeys...
Carina Cortez: I'm one of the rare people who knew that they wanted to pursue a career in the field they studied in (HR Management). My first job was at Visa, via my dad's friend's wife (networking is key!) where I worked my way up from an HR Receptionist to an HR Business Partner (HRBP). While on maternity leave, I was recruited by the former CTO of Visa to go to PayPal (after interviewing me when I went to visit the office to show off my baby!) At PayPal, I moved from HRBP into HR Strategy & Operations before Learning & Organisation Development. My boss at the time moved to Walmart and, after around two years, I left PayPal to become the HRBP for the CTO of WalmartLabs. To continue progressing at Walmart would have required a move to Arkansas, which was not the right move for my family. I instead moved to Ellie Mae as Chief People Officer before most recently joining Glassdoor.
Annie Pearl: 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 which led me to become involved in and lead product management. I realised I was a lot more interested in building products and seeing how my ideas could come to life to solve real problems for people. After about four years, I moved to Box which was in a different phase of growth and 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.
Kate Ahlering: For me, landing in sales was a relative inevitability. Both of my parents spent their careers in sales and revenue leadership positions, so I often joke that I was born in a sales petri dish. However, my start in sales wasn’t necessarily deliberate.
During one of my first interviews post-graduation, I sat down in front of a fantastic woman who would end up being my boss for many years. At the time, I was deciding between pursuing sales or marketing. She asked if I knew the difference between the two, and I’m certain I wasn’t anywhere close to the right answer. She looked at me and said, “I think you should be in sales.” The rest is history.
What Are Your Biggest Career Learnings So Far?
Carina Cortez: If you don't know, say you don't know! Don't make up an answer or pretend you know everything; ask for help when you need it. Secondly, be authentic; people can see through the b*******. Be true to yourself and operate from a place of values and integrity. You've gotta be able to look yourself in the mirror and be comfortable with what you see at the end of the day. Annie Pearl: In one of my earlier jobs in a start-up, 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. Success often comes more from what you don’t do, than what you do. Kate Ahlering: On my first day in an internship, I was asked to make coffee. However, I had no idea how to make coffee. Not wanting to admit that I didn’t know how, I gave it my best shot and…let’s just say it didn’t go well! In the aftermath of the ordeal, my manager asked, “why didn’t you just say you didn’t know how?” That experience was a great learning lesson for me, and I’ve carried it with me since. If you don’t know how to do something, don’t be too proud to ask for help. Secondly, trust your gut. It got you this far, most likely it will take you even further. As you progress in your career, the less feedback you get and the more you naturally start questioning your intuition. It’s an odd dichotomy — your influence grows but your guideposts get further and further away. Trust in your instincts that got you to where you are.
Who Has Been The Biggest Influence On Your Career?
Carina Cortez: My friend/mentor/former boss: Lou Sanchez. He was the hardest on me, had high expectations, and set really high goals for me. But he coached and mentored me along the way, gave me tough feedback and had my back. He took a chance on me and this really propelled my career.
Annie Pearl: 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.
Kate Ahlering: I’ve been fortunate to have a few unofficial advisors that helped build my career. For example, early on in my career, a senior executive generously agreed to have breakfast with me every couple of months. We never had a formal agenda but I came with questions, he talked about what was happening in the business, and I learned a tremendous amount from him. That small investment of time meant a great deal to me; he was very influential in the early days of my career. I still apply a lot of the lessons I learned from him today.
Finally, What Is Your One Piece Of Advice For Job Seekers Today?
Carina Cortez: Trust your instincts. If something is telling you to take a job/apply for a job you don't think you're fully qualified for - take it. If something is telling you to not take a job because something just doesn't feel right - trust that feeling and walk away...a better opportunity is waiting for you. Annie Pearl: Don’t think about your career as a set of logical, sequential steps up a ladder but, to quote Sheryl Sandberg, as more of a jungle gym. Focus your job search on finding opportunities where you can maximise learning and growth above what might feel like the next step up the ladder is. Kate Ahlering: Use Glassdoor, of course! Also, I subscribe to the 5 P’s - proper preparation prevents poor performance. It sounds simple but doing your research on the company, the industry, your interviewers, others in similar roles, etc will set you apart as a candidate. If you demonstrate the drive to thoroughly prepare for your interview opportunity, that will most likely translate positively to the hiring manager.


Glassdoor Team
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