Eighty-seven.
That’s the number of women promoted to management positions for every 100 men in the United States, according to McKinsey’s 2022 Women in the Workplace study. And that disparity is even larger for women of color.
But, women are just as ambitious as men. According to data from Gallup, 45 percent of American women in the workforce aspire to become an executive. Meanwhile, only 25 percent of C-suite roles are held by women.
Yesterday was International Women’s Day. The day commemorates when New York City garment factory workers — most of whom were women — went on strike for better working conditions in 1908. Each year, March 8 celebrates women’s achievements and calls for gender parity.
Women looking to become leaders face headwinds that make it harder for them to advance when compared to men — even getting over the first “broken rung” of the ladder into a management position provides a major hurdle. So this year, in celebration of International Women’s Day, Built In San Francisco talked to women who have beaten the odds in moving to management positions. Here are their insights for the next generation of leaders to come.
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What’s the most important lesson you learned as you grew your career?
In my 30s, I got several quick promotions and I was on top of the world. Then, I began to get feedback that I was intimidating, not relatable and arrogant. Those were hard words to hear, but I needed to hear them in order to grow. Despite my strengths, there was one strength I was missing: humility. I didn’t ask enough questions, and I didn’t spend enough time listening. When I couldn’t see the reason why I was doing something, I assumed I knew better. Those whose wisdom I failed to respect watched me charge forward and fail, knowing that they could have helped me had I simply thought to ask them.
I missed opportunities to build consensus, learn and give others the chance to feel heard and valued. I might have learned that there were bigger opportunities for improvement or changes that had been tried but failed, and why. Now, I spend more time reading, listening and asking questions. I formulate ideas for change and then get feedback before acting. When a process or a report seems illogical, I ask why we’re doing it that way. Sometimes there’s a good reason, sometimes not, but the answer always teaches me something.
How do you stay motivated and inspired as a leader, and how do you try to motivate and inspire other women at your company?
When it comes to motivating and inspiring others, I have always tried to be authentic and vulnerable. When things are hard, I don’t pretend they’re not. I have had more than one person tell me they appreciate that I say out loud the thing that everyone is thinking but no one wants to say. I like to think that I have opened the door to conversations and solutions that would not otherwise have been possible. I hope that I’ve shown others that they can take that risk, too, and it’s possible to say uncomfortable things while still finding success.
When The Going Gets Tough
“In any career, there are times when everything is going right and the enthusiasm comes naturally, and others where it’s a struggle. During those times, I lean on a technique called ‘good work journaling’ that I learned from the book, Designing Your Work Life,” said Whitehead.
How does it work? At the end of each day, take some time to reflect and jot down a quick note in three areas:
1. What did you learn?
2. Who did you help?
3. What did you initiate?
“This practice not only helps you see where you’re making a difference, but it also reminds you to invest time in each of those areas each day,” said Whitehead.
What advice do you have for the next generation of women in tech, and why is this advice important?
Raise your hand for that assignment that is so hard that no one else wants it.
About 10 years ago, I left accounting for finance. It was a tough first year and, at the end of it, I was offered an opportunity to move to the more technical side of finance. I started a brand new team that would build econometric models to forecast financial results.
I was in the middle of my MBA program at the time, so I pivoted a bit to complete a concentration in analytic finance. At first, I felt like an absolute fraud, but eventually I gained enough technical knowledge to feel at ease, and I began to realize how helpful my accounting, financial reporting and business expertise was to my team of modelers. It was both the hardest and the most rewarding job I’ve ever had. The impact on my career was dramatic because it taught people — and myself — that I could learn new tricks, I was flexible enough to adapt my leadership skills to new challenges, and I worked well under pressure. Not every challenge will end in success, but if you never fail, you’re not trying hard enough.
If you never fail, you’re not trying hard enough.”
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What’s the most important lesson you learned as you grew your career?
The most important lesson I learned was to recognize that I’m responsible for my career growth and need to advocate for myself. I figured this out when I inadvertently stalled my career by getting too comfortable and not requesting to take on new challenges. Early in my career, I was with the same company for nine years and, unfortunately, did the same thing for seven of those years. While I was confident in my abilities and enjoyed the people I worked with, I was in maintenance mode with the software and my career. I wasn’t learning anything new and I had become an expert in a dying technology.
I finally realized my manager couldn’t read my mind, and it was on me to speak up and request to switch to another project. Even though learning a new technology put me outside of my comfort zone and felt like starting over again, it was an important lesson I wish I had learned sooner. There is no growth without discomfort. You might even fail along the way, but that’s all a necessary part of the learning process.
How do you stay motivated and inspired as a leader, and how do you try to motivate and inspire other women at your company?
Leadership is not about stroking your ego, and it doesn’t generally come with a lot of praise. Instead, I am motivated by the recognition my team receives. Even more so when they say they enjoy what they do, yet they are still challenged to learn. I am inspired by the growth I see in my team and the cohesive feeling of working towards the same goal. That also motivates me and assures me as a leader that we’re on the right path.
I want to inspire other women by showing them that you don’t have to be a man to do this job. I started my career in 1996 when there were a lot fewer women in technology to look up to, so I hope I can be a positive role model for others. Ultimately, I try to lead by example, and part of that is to treat everyone equally. Regardless of gender or ethnicity, I think everyone should be given the same opportunities and held to the same standards.
I want to inspire other women by showing them that you don’t have to be a man to do this job.”
What advice do you have for the next generation of women in tech, and why is this advice important?
A lack of confidence can hold you back from putting yourself out there and seeking the help required to grow your skill set. I don’t pretend to be an expert at anything, and if I don’t know something, I will ask a person who does. I also recognize that I still have plenty to learn and that’s OK too. I was self-taught in some portions of my career and that often wasn’t the best way to learn. I missed out on different solutions and approaches to a problem and unnecessarily repeated mistakes others had already made. I strongly encourage other women in tech to find a mentor you trust and allow yourself to be vulnerable. While it’s great to be self-sufficient, trying to figure it all out on your own could have a negative impact on your career.
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What’s the most important lesson you learned as you grew your career?
One of the most important pieces of advice I learned as a leader was never to be afraid to hire people that are smarter than you or know more about a particular subject.
This can be especially difficult for women, because we are often self-conscious about showing a vulnerable side of ourselves. But the reality is: As a leader, you will not always know the answers or the best way to approach things, or be an SME in every aspect of your role. So, in order to succeed, you want to build a team of other team members that can complement and supplement your knowledge and skills.
Never be afraid to hire people that are smarter than you.”
How do you stay motivated and inspired as a leader, and how do you try to motivate and inspire other women at your company?
I stay motivated by building an amazing team of leaders and individual contributors. Hiring other leaders and surrounding myself with leaders that share the same values as me is really important and probably the single most influential way I stay and get motivated. I like being with other leaders that challenge me and our way of doing things. I like being with leaders that have a sense of humor, and don’t take themselves too seriously but also want to improve things, empower their teams and build something new.
I try to motivate women by providing them with the true support that is needed during life changes — especially when taking a leave of absence (most often related to maternity leave). I wholeheartedly support and believe that women can and should have successful careers at all stages of their life and should not be inadvertently “dinged” by missed or limited opportunities due to family needs.
What advice do you have for the next generation of women in tech, and why is this advice important?
Seek out and establish mentors early in your career. I do not mean formal mentors, but people in your professional world whom you trust and respect. Try to connect with them several times a year and discuss some very specific scenarios. Ask questions such as: “How would you have handled X?” “What should I consider before Y?” “What skills are required for Z?” Or tell them about a situation you are dealing with.
This will provide you with different perspectives on how to handle different situations. By discussing these scenarios, these trusted confidants will also get to know you more, so as you grow in your career, they can help point out patterns, understand your references and, ultimately, help you in some of your career choices and opportunities.
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What’s the most important lesson you learned as you grew your career?
Starting out as a bright-eyed, intimidated associate in a big law firm, I believed I had to conform to a few fairly established standards to be successful. I realized that these standards didn’t completely align with my experiences, background, and my natural self. I reached out to a firm partner for advice on how to not only survive, but thrive in this environment. The advice she gave me was to always observe and learn from others, and to ultimately embrace my own style and journey because that will be the path to my true success. As I’ve grown in my career, this advice has proven invaluable. It gave me the freedom and confidence to incorporate my unique style and individuality to my work. The realization that there is no singular model to success has also allowed me to take on roles that aren’t in my core area of expertise. By taking the time to observe and learn from others, I am able to find the commonality in our shared experiences and to embrace differences, while navigating the challenges of collaborating with people from different areas of expertise, backgrounds, cultures, and perspectives.
Always observe and learn from others.”
How do you stay motivated and inspired as a leader, and how do you try to motivate and inspire other women at your company?
I am motivated and inspired when I am passionate about the work I am doing and the impact I can have. For this very reason, I find myself very drawn to working for companies who are mission driven and focused on serving communities, like VSCO. As a child of immigrants, I found joy early on in helping resolve issues for others, being an advocate, and working collaboratively to find solutions. I am passionate about protecting our business by managing risks and challenges and take extreme pride in our work to keep VSCO a safer place for our creator community with our Trust & Safety efforts. It’s critical to find what drives you. I know that it can be a privilege to be able to do what you love, but I would encourage people to try new things to realize what brings them joy or feels rewarding. For example, if you are in a role that requires more individual contribution, but you love meeting with others, seek opportunities to serve on interview panels, be involved with company social events, or participate in an employee resource group. If you find that your day to day can be draining, perhaps find a passion externally that fills your cup and provides energy for you to thrive.
What advice do you have for the next generation of women in tech, and why is this advice important?
Quiet that inner voice when it holds you back: I, like many others, have had an inner critic at times who makes you question if you are ready or great enough. This critic has kept me up at night, made me show up less confident in certain situations, and at its worst prevented me from realizing the value I can bring to the table. I believe this voice can be more acutely heard when you are the only female or part of a small minority in the room. It’s critical to tell yourself that this will continue to be the narrative and status quo if you let that voice hold you back, and to positively envision yourself as ready and good enough.
Invest in relationships, which should include advocates and mentors: I am fully aware that I’m where I’m at today because I had not only mentors, but also incredible individuals who went above and beyond to advocate for me. I also believe that I wouldn’t have connected with these folks had I not been open to new opportunities and made an effort to connect with others on a deeper level.
Don’t forget your oxygen mask: It’s important to take that time for yourself — to exercise, take mental breaks throughout the day, and schedule time for you!
