The Important Lessons 6 Women in Leadership Learned Over Their Careers

These women have ascended to leadership roles in a male-dominated industry, and have advice and wisdom for fellow women in tech.
Written by Lucas Dean
March 7, 2023Updated: April 5, 2024

“If your actions create a legacy that inspires others to dream more, learn more, do more and become more, then you are an excellent leader,” Dolly Parton once said.

Women leaders around the world have created their own legacies and continue to build a better future for their peers. On International Women’s Day, we’re provided an opportunity to celebrate advancements in representation, equity, reproductive rights and more while acknowledging the many areas where more progress needs to be made. 

In the workplace, more women hold positions of power than ever before. Overall, women hold a 31 percent share of leadership positions, according to a World Economic Forum report from 2022. However, in the tech industry, women account for only 24 percent of leadership positions. Relative to other industries, tech’s gender parity score falls behind 13 others. 

As women push for more opportunities for ascension in the workplace, women who lead can draw from their own experiences to offer invaluable lessons and advice. By sharing this knowledge and expertise, women who aspire to lead can be uplifted and empowered to do so confidently and authentically. 

“As a woman leader, I have learned there is power in being vulnerable, and people are inspired by those who have shared similar experiences,” said Director of Client Success, North America, Ellery Shawver, who works at Reachdesk. “If we are adding value to those around us, then we are setting ourselves up to all rise together.” 

Shawver and five other women in leadership reflected on the important lessons they’ve learned throughout their careers and as leaders, and shared advice for fellow women in tech. 

 

ROKT team members speaking on a panel.
ROKT

 

Holly Aresty
Deputy Chief Commercial Officer • Rokt

ROKT provides e-commerce companies with solutions to grow revenue, acquire new customers and build customer loyalty. 

 

What’s the most important lesson you learned as you grew your career? 

One of the most important lessons I’ve learned over the years is to embrace change. In business, as in life, change is inevitable. I actually learned this early in my life due to several life-changing events I went through growing up, but I didn’t realize the impact of this quality until much later. For the first few years in my role at Rokt, the imposter in me was constantly questioning my value: “What am I bringing to the table when I’m rarely if ever the smartest person in the room?”

A few years into my tenure, we rolled out a new hiring process that consists of a final round interview during which we screen candidates for specific values to make sure they align with our culture, and this is when it clicked for me. One of these values is demonstrating resilience in the face of adversity or, in other words, embracing change. The more I learned about this trait, the more I understood my value. I learned that resilience can actually help people overcome weaknesses in other areas and carry them through to get to the outcome they desire. So while you may not be the smartest person in the room, your resilience can enable you to accomplish just as much — if not more —than 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?

For me, it really comes down to the environment, culture and people I surround myself with. You have to wake up every day excited about the challenges you are facing and the people that you are facing them with. I’ve been in situations before where I wasn’t, and that makes it nearly impossible to stay motivated. And while days, months and years are full of ups and downs, if you’re passionate about what you’re doing and if you thrive off of those around you, it will fuel you and motivate you like nothing else. 

A huge component of that is being a part of a culture that is authentic, which ties into how I motivate and inspire other women. I lead through my own authenticity and vulnerability, creating safe spaces for people to ask questions and make mistakes. I’m the first to admit my own mistakes and take ownership and accountability for them. And I need to be in an environment where others do the same.

I lead through my own authenticity and vulnerability, creating safe spaces for people to ask questions and make mistakes.”

 

What advice do you have for the next generation of women in tech, and why is this advice important?

My advice is to cultivate genuine relationships whenever possible. Business is as much about relationships as it is about strategy and performance. When you know and trust people, and when they know and trust you, opportunities multiply. I am always in awe of people who are really good at this since it’s something I’ve always wished I was better at. In the past, I think I viewed this as being social after work or creating friendships outside of a professional setting, which wasn’t something that came naturally to me. But through the years, I’ve realized you can still have professional relationships built on trust and respect. 

You do have to put in the effort and really get to know someone, understand them on a human level and show your own vulnerability in return, but you don’t have to party with them every weekend — unless you want to! Strong communication skills, like keeping in touch with people over the years even when you no longer work together, and empathy, like offering to help in situations where you can, go such a long way in building these relationships. The energy you put into this will come back to you in spades.

 

 

Ada Phang
Managing Director, Head of Business Development • Keyway

Keyway helps commercial real estate investment companies and property sellers make transactions more quickly and efficiently. 

 

What’s the most important lesson you learned as you grew your career? 

I learned to give myself a little credit instead of filling myself with fear and self-doubt. When I was pregnant, I was nervous about telling people and tried to hide it for as long as I could. I was so afraid — afraid that I would be replaced, that clients would forget about me, that I wasn’t all that valuable and that the few months away would let the company find that out. 

Ironically, my employer could not have been more supportive, but I was my own worst enemy and kept myself from seeing my worth as much as they could. Then maternity leave came and went, and while schedules changed in a big way, my abilities didn’t. When someone commends me on a job well done, I try to remember to give myself an internal pat on the back instead of sheepishly saying I was just lucky. I try to remind myself to be more conscious of when I’m the one beating up my own confidence because I don’t want fear that I inflict upon myself to hold me back from speaking up, raising my hand for a new initiative and setting out to accomplish amazing things.

 

How do you stay motivated and inspired as a leader, and how do you try to motivate and inspire other women at your company?

Making a meaningful impact keeps me motivated. My parents immigrated here without much and never felt financially secure until they owned their own home. They felt secure knowing that if they needed to, they could sell the property because there was liquidity. There may be fluctuation in price, but they know they can sell it. Keyway connects owners of small-scale commercial real estate with buyers, providing a source of liquidity to owners who might otherwise not have had access to capital outside of their local area. Opening up liquidity adds financial security for these folks, and that’s meaningful to me. 

As for motivating and inspiring other women, it’s something I’m working on. I’ve given advice when asked, but I never felt like I was in a position to be imparting words of wisdom. This goes back to my self-doubt. I’m afraid that I’m not smart enough, good enough or wise enough. But I’m learning that advice doesn’t have to be an enlightening epiphany, and I can be helpful by simply sharing my experiences. I’m going to try to be more open and candid about my mistakes and wins with other women because these stories from other women have helped me along the way.

I’m learning that advice doesn’t have to be an enlightening epiphany, and I can be helpful by simply sharing my experiences.”

 

What advice do you have for the next generation of women in tech, and why is this advice important?

Be authentic about who you are, not only externally but internally as well. Early in my career, I spent a lot of time trying to fit a mold or standard of who I thought I was supposed to be. Growing up in the finance and real estate fields, there weren’t many diverse images of what a successful person looked like, so I allowed my definition to become quite narrow. 

I started to want things I didn’t really want and be someone I didn’t really care to be. I let myself forget that part of my value is that I’m different and have unique perspectives to offer. Trying to pretend to be a rockstar version of myself by emulating a rockstar version of someone else wasn’t going to put me on a path that was mine, and it took a long time for me to walk back and figure that out. Your quirks are what set you apart, and your insecurities may be your strengths in others’ eyes, so be clear and authentic about who you are — especially to yourself.

 

 

Yolonda Smith
Sr. Director, Security Engineering • Grubhub

Grubhub is a global food delivery marketplace used by over 33 million people. 

 

What’s the most important lesson you learned as you grew your career? 

As my career has progressed, one of the things that I have learned and have often come back to is to keep the end goal in mind, especially when the path to get there is unclear. Sometimes this means relinquishing a bit of control and making myself vulnerable to trust that my peers and team members understand my vision well enough to execute it effectively. One of my mentors once asked me, “Do you want to be rich or do you want to be a king?”, meaning is it more important to reach the end goal or is it more important that it gets done exactly your way? When I was a new people leader, it was more important for me to be a king to build and enforce standards, but as I’ve come into more senior leadership roles, it’s become much more important to ensure that I clearly communicate the desired end state — the what, why and, to a degree, the when — and trust that my team will get us there — the who and how.

 

How do you stay motivated and inspired as a leader, and how do you try to motivate and inspire other women at your company?

One of the things I struggle with is focusing on all there is to do versus what I was able to get done. It can be very demotivating. To counteract this, I do two things. First, I start every day with a blank sheet of paper, mostly for note-taking. When it’s blank, there are no unfulfilled expectations and no follow-ups, just a fresh start every day. At the end of every day, I look at what is typically a full sheet of paper, and I circle three things I’m really proud of or grateful for. At the senior levels, you don’t get as many pats on the back for regular stuff, so it’s important to shout out yourself sometimes, even if it’s in your own office by yourself.

When it comes to motivating other women, especially women in tech, one of the things I try to do is to provide direct, positive feedback whenever I have an opportunity. Just like for myself, I like to try and show people how far they’ve come and the difference that they’ve made, even on seemingly little things.

Just like for myself, I like to try and show people how far they’ve come and the difference that they’ve made, even on seemingly little things.”

 

What advice do you have for the next generation of women in tech, and why is this advice important?

Resist the inclination to blend into the background in order to be seen as a team player. Why? Because your work doesn’t always speak for itself. I know not everyone is comfortable with being in the spotlight or speaking up in the moment, but I have found that women, more often than the men on my teams, have really good ideas and solutions that they’ll tell me after the meeting is over or when we have a private conversation. 

My response is always, “Why didn’t you say that out loud when we were all together?” And the answer I get is always something like, “I didn’t want to contradict my male colleague. He probably knows more than me.” Guess what? He doesn’t — he’s just louder than you. Being a good team player isn’t going along to get along; it’s also helping the team to recognize all of the angles and opportunities to solve a problem. Not all of your ideas will survive first contact, but if you never say them out loud, it will be more difficult to distinguish yourself as an impact-maker.

 

 

Ellen Brandenberger
Director, Product Innovation • Stack Overflow

Stack Overflow is used by developers and engineers to solve problems and share knowledge, while products include employer branding, advertising and content. 

 

What’s the most important lesson you learned as you grew your career? 

I constantly push myself out of my comfort zone to accelerate my professional learning. I consciously step into those opportunities and bet on myself to grow quickly to meet a new standard. This is rooted in a mindset that learning never stops in my career and is its purpose. 

For example, my first product role was highly technical, which I was not. Later on, I was asked to take on a huge release, normally led by someone more senior, and executed successfully! When a new product team opened, I was recommended to be its first product manager. I was hungry to learn, so I joined an early-stage startup and then led a small product team at that company. I liked management so much that I applied to lead a bigger content team. Within a few months, a new executive position at my company opened, and I ultimately got the role. Less than a year after becoming a manager, I led a 25-plus-person team! 

All told, never stop growing. If you bet on yourself, deliver results and act with humility, you will discover new opportunities you hadn’t considered. And if you do this with compassion and via collaboration, people will want to work with you and for 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?

Motivation is fundamentally personal. Some of us value income, prestige or other external factors, while others are motivated by internal feelings, types of work, collaboration or social recognition. 

With my new team, I think I’m certainly still learning how to motivate them best, but I usually consider two things.

What motivates them personally? As a leader, can you align this personal motivation with the goals of the company and team? Aligned incentives are where the magic happens for teams; they reach their goals while doing work that inspires them! 

Leading with evidence, context and problems to solve — versus tasks, mandates and so on — helps ensure teams are empowered to find the right solutions to drive their desired outcomes. I’m motivated by doing work I enjoy that solves a problem that matters alongside smart people. It took me a while to figure this out, and I’m still refining, but it became most clear at points in my career when my motivation was at its lowest and things that had previously felt easy suddenly felt like huge challenges. When I asked myself what was missing, these things came to light, and I focused my energy on making choices that maximize these variables.

Leading with evidence, context and problems to solve —versus tasks, mandates and so on — helps ensure teams are empowered to find the right solutions to drive their desired outcomes.”

 

What advice do you have for the next generation of women in tech, and why is this advice important?

Find mentors, coaches, peers and advocates. Your career is inherently a social journey and relationships matter most. You need mentors who can inspire you, coaches to guide you, peers who can push you and advocates who can speak for you in new or bigger arenas. Invest time into finding each of these relationships and giving back to others in the same way. It will help you grow more than you can imagine! 

It’s a marathon, not a sprint. Your career is long, and you don’t need to figure out everything right away. Figure out what matters to you right now, master that, and then keep moving forward, but remember that you will do your best work if you are happy, healthy and if you love the life you’ve built outside of your career.

 

 

Reachdesk team members pose for a lively group photo at a summer party.
Reachdesk

 

Ellery Shawver
Director of Client Success, North America • Reachdesk

Marketing tech company Reachdesk provides integrations to company tech stacks that automate complex processes and engage with customers with direct mail. 

 

What’s the most important lesson you learned as you grew your career? 

It was through a previous leader I was taught one of the most powerful lessons: the importance of managing up. Understanding what this meant has played a pivotal role in evolving who I am as a leader and a direct report. Whether you’re an entry-level employee or a seasoned executive, taking time to understand and communicate with those above could be the differentiator between you and someone else. This means taking the time to cultivate a productive working relationship with your boss, the willingness to adapt to their management style and the ability to empathize with them by putting yourself in their shoes. Be the person who presents solutions, not just problems, who shows they care through observation, fallibility and curiosity, and someone they know can deliver results regardless of circumstances. 

 

How do you stay motivated and inspired as a leader, and how do you try to motivate and inspire other women at your company?

My motivation stems from the opportunity to be in an environment that values my worth, celebrates my successes and humanizes the expectations of a job. Whether it’s big or small, if I am given a chance to learn something new, fail by trying or provide a piece of advice, then that’s enough to motivate me to want to do it again tomorrow. 

As a woman leader, I have learned there is power in being vulnerable and people are inspired by those who have shared similar experiences. If I can put down walls that might allow the women around me to be inspired, then there is motivation in that alone. 

If I can put down walls that might allow the women around me to be inspired, then there is motivation in that alone.”

 

Empowering also means finding other ways to connect, mention, recognize and embrace our women colleagues. If we are adding value to those around us, then we are setting ourselves up to all rise together.

 

What advice do you have for the next generation of women in tech, and why is this advice important?

It’s fair to expect our places of work to have our best interest in mind, but there will likely be a time in your career when you are just a number. One thing you can do to change that narrative is to consistently advocate for yourself. Communicate your career goals, vocalize your wins, hold people accountable and don’t be afraid to ask for what you deserve.

Call me naive, but I expected my superiors to know what value I was bringing, to make sense of it, keep track of it and act on it. I learned that oftentimes your value isn’t as visible as you think it is. So if you are working on a project behind the scenes or received a complimentary email from a customer, shout it from the rooftops. Keep track of those things and share them. And when it comes time for your next performance review or a potential promotion, you are well positioned to have a positive conversation. 

 

 

Bailey Acevedo
Chief Operating Officer • CertifyOS

CertifyOS is a provider platform powered by API integrations and data points to offer licensing and enrollment, one-click credentialing and real-time network monitoring. 

 

What’s the most important lesson you learned as you grew your career? 

The most important lesson I’ve learned is that everyone, at some point or another, makes mistakes on the job. How you handle the mistakes is what will make or break you. I always tell my team that it is OK to make mistakes so long as you are honest about mistakes when they happen, take accountability for them and don’t try to sweep them under the rug, and learn something from them. 

In my very first job out of law school, I was assisting a client with an external appeal so they could receive a very needed medical procedure. I had a high caseload at the time and lost track of the deadline for this one case, and missed the mailing deadline by two days.

Following this, we implemented an appeals calendar to try and provide a safety net to busy lawyers. I could have handled this differently. I could have tried to blame the mailroom for not mailing the packet out on time, or I could have sent the appeal late, knowing I’d receive a denial letter. But I didn’t do either of those things because accountability is important to me. 

I now try to create an environment where people feel safe to tell me if they make mistakes, so long as we continue to learn from them.

 

How do you stay motivated and inspired as a leader, and how do you try to motivate and inspire other women at your company?

One of my own personal values is to always continue to learn. I read a lot of biographies about successful business leaders and try to find lessons and learnings from their experiences that I can apply in my own career. I’ve also continued to use platforms like LinkedIn Learning, the Disney Institute and university executive education programs to continue building skills. I learn something new every day and try to apply those learnings to my daily tasks. 

I also try to take a personal interest in all of my employees. I have meetings with every member of my team, regardless of level, when they join the organization and then have group sessions, bi-weekly skip levels, and twice-yearly one-on-ones with more junior team members to try and stay connected and listen to feedback. Another one of my values is that I truly believe good ideas come from anywhere, but you will not be able to hear them if you’re not staying connected to your team.

I truly believe good ideas come from anywhere, but you will not be able to hear them if you’re not staying connected to your team.”

 

What advice do you have for the next generation of women in tech, and why is this advice important?

The most important piece of advice I have is that no one will be a stronger advocate for you than yourself. Earlier in my career, when I excelled in my work and surpassed goals, I waited for others to recognize my achievements and hopefully reward me with compensation increases, bonuses or promotions — with mixed results. Some managers recognize when someone is shy or worried that they will come off as “bragging” about their accomplishments and will help them fill the gaps. But many don’t. 

After going through many performance review cycles and calibration sessions, I’ve learned that it can be a relief to managers if a solid employee hasn’t made demands when others on their team have. The solid but quiet employee may get bumped to the bottom of the promotion and new compensation pool, while colleagues that have advocated for themselves may surpass them, even if the noisier employees’ performance isn’t better. Make sure your managers are aware of your goals and of what you’re bringing to the table. Share your results, and if you think you’re ready to take the next step, have transparent conversations with your managers or people partners about what it will take to get there.

 

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