‘Like Learning To Surf’: Reflections From 9 Women On Their Paths To Leadership

Though these featured women faced obstacles, they persevered and learned how to ride the wave to the top.
Written by Olivia Arnold
March 8, 2023Updated: March 8, 2023

Olga Andrienko wants the next generation of women in tech to approach their careers like learning how to surf. 

In the beginning, a new surfer is inevitably going to fall off their board and swallow some salt water. In those moments of frustration, Andrienko sees two options: give up or stick with it. 

“You can choose to focus on working toward feeling free and riding the waves one day,” said Andrienko, who is vice president of brand marketing at Semrush. “The decision that you make determines how quickly you make progress. Embrace challenges, as this is what helps you grow as a professional.” 

Andrienko is one of nine leaders being featured by Built In Austin for International Women’s Day. Celebrated annually on March 8, International Women’s Day recognizes women’s societal contributions while pushing for greater gender equality. 

Though these nine women have faced their fair share of obstacles in the tech industry, they persevered and learned how to ride the wave to the top. Now, they have essential wisdom to share with fellow women technologists about the importance of taking risks, finding support systems, developing your skill sets and charting a path to leadership.

 

Jessica Rivera
Lead People and Organizational Development • WISE

Wise is a fintech company that enables cost-effective international money transfers. 

 

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

Years ago, my department director started a meeting by making eye contact with each one of us and saying, “Everyone in this meeting is replaceable.” I was stunned and a bit offended. 

He went on to explain that if any of us decided to leave, the company would move on by finding someone equally capable and talented to fill the position. In business, everyone — including the department director himself — is replaceable. However, to each of our family and friends, we are irreplaceable. It's important for us to realize and acknowledge this fact and always remember where our ultimate priorities rest. 

Hearing such an important message from leadership about work-life balance so early in my career shaped my approach to work and had a lasting impression on me. I'm not always great at it, but when I'm taking on maybe a bit too much at work, I think back on that moment. I am able to reframe my thinking and prioritize what I should focus my attention on versus what I can delegate or say no to.

 

How do you stay motivated as a leader, and how do you inspire other women at Wise?

Being responsible for the employee onboarding experience at Wise, I have the privilege of being part of the start of so many career journeys. I love sharing that excitement and passion with my team. 

Mentoring others is so rewarding, not because I think I have all the answers, but because I share my missteps and the insecurities that I had in my early career. Imposter syndrome was a big shadow that loomed over me for longer than I care to admit, and it was something that in many ways was self-imposed. 

Being able to encourage and coach others to reach their potential is such an amazing gift because it also helps me develop into the best version of myself. In an environment where we celebrate each others’ strengths and achievements, we are all able to grow.

 

Have confidence in the value that you bring to the table, find your voice and be brave to share your talent with the world.”

 

What advice do you have for the next generation of women in tech?

First, keep learning. Even in failure, there is a lesson to be learned, and having a growth mindset is critical to developing grit and resilience. 

Second, network. You never know where opportunities may present themselves. Networking provides you with a diverse support system, increased visibility and opportunities to learn, be curious and meet some really cool people.

Third, believe in yourself. Have confidence in the value that you bring to the table, find your voice and be brave to share your talent with the world. 

 

 

Veronica Servantez
SVP, Marketing and General Manager, Small Business • BigCommerce

BigCommerce brings online selling solutions to merchants ranging from small startups to large enterprises. 

 

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

The most important lesson that I’ve learned throughout my career is that we are capable of more than we think. This has become a mantra that I’ve gone back to time and time again whenever I was presented with a new challenge or opportunity. 

I try to instill this in my teams, especially young leaders who are taking those initial leaps in terms of scope or responsibility. Early in my career, I was hesitant to raise my hand or stretch professionally. It was usually a boss or leader who “voluntold” me or pushed me into a new, more challenging role. 

I initially believed that I needed to be an expert in a particular area to provide value or succeed, but after a few times of stepping up, I found that I was more than capable. I discovered that I actually thrive and am most fulfilled when I’m a bit out of my comfort zone. 

I’ve learned to be comfortable with the uncomfortable; that’s where growth happens. I have a thirst for learning and no ego when it comes to asking even the most basic questions. I’ve learned to leverage my skills, strengths and even limitations when facing any new challenge or opportunity.

 

How do you stay motivated as a leader, and how do you inspire other women at BigCommerce?

A big part of staying motivated for me is to ensure that I keep learning and challenging myself, and I encourage the same in my teams. 

I get genuinely excited when I see teammates and peers striving to meet and exceed their potential. I welcome and encourage teammates who bring new and different perspectives to the table. I often learn from my teams, and that’s always inspiring.

My role is to support, encourage and shine a light on the leaders of tomorrow. Women in my company often reach out for personal guidance and support, and I always prioritize making time for them. Sometimes, just hearing from a woman leader who has faced similar challenges or wrestled with similar questions and situations is helpful. 

A key part of my role as a leader is to actively champion new ideas and ensure emerging leaders, regardless of gender, get visibility as they advance in their careers. That is one of the most inspirational and fulfilling parts of my job; it fills my cup.

 

If there’s an opportunity that equally excites and scares you, take the leap. Whether you fail or succeed, as long as you learn from it, you’ll be smarter and stronger for it.”

 

What advice do you have for the next generation of women in tech?

I would give them the same advice that I would give myself if I could time travel: Be curious, ask questions and find what excites you. 

If you have an idea, speak up. If there’s an opportunity that equally excites and scares you, take the leap. Whether you fail or succeed, as long as you learn from it, you’ll be smarter and stronger for it.

Don’t sell yourself short and, when you do climb that ladder, don’t forget to reach out a hand to help the next generation of leaders take that step up with you.

 

 

Brenda Contreras
VP of Engineering, Head of Architecture • Self Financial

Self Financial helps people establish their credit through affordable financial products. 

 

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

The most important lesson that I have learned is that knowledge is power and staying in tune with the latest technology trends and patterns was key to moving up the career ladder. 

Early in my software engineering career, I applied for several architecture roles and kept getting rejected. My technology experience was only as deep as the type of systems that I had touched, so I started to do research in other areas of software and technologies that I had not used before. 

My continued technology depth from research, along with the capability to storytell on how certain design patterns serve business and product strategies, have been key to my career success.

 

Staying in tune with the latest technology trends and patterns was key to moving up the career ladder.”

 

How do you stay motivated as a leader, and how do you inspire other women at Self Financial?

I get excited every day to be able to set the tech vision for the company and how we should build our software to support the business. My leadership approach is very collaborative, and I get super motivated when the people I lead start identifying new tech solutions and tying the tech approach to business objectives. 

I think I inspire other women at my company by representing tech at this level. I am a big advocate for women in tech. We host quarterly events at Self Financial for employees and women in the community to network and speak on topics that impact us. I am also a mentor for several women and have an open-door policy for anyone to ask me anything.

 

What advice do you have for the next generation of women in tech?

My advice for the next generation of women in tech is don’t give up and don’t be afraid to try new things. 

In tech, there are several career paths that one can take. These paths make the difference between being a front-end, back-end or full-stack engineer, a manager or an individual contributor. Test drive roles. Try something new and get hands-on experience to decide whether that role is for you. The worst thing that can happen is you gain experience in a new area.

 

 

Kim Barney
VP, Customer Success and Support • ESO

ESO provides software for emergency medical services, fire departments and hospitals. 

 

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

Speak up, ask questions and don't be afraid to challenge the status quo. When you ask questions, you will learn something. You might learn the answer to your question, something about the person answering or how others respond. All are valuable and will help inform how to operate in the future. 

I also love to ask “what if” questions to imagine something differently. This often leads to new and exciting approaches to business issues or needs, and it can help unlock others’ passions and talents.

 

How do you stay motivated as a leader, and how do you inspire other women at ESO?

My main motivation is my family, especially my children. I am raising five boys and I love showing them what I can do in the business world. They don't question my value as a woman or my seat at the table, which is important. I love talking business with them and sharing some of my lessons learned over the years.

In the office, I am motivated by the constant evolution of the customer experience. I love to look at the most efficient, effective and engaging ways to help our customers and internal team members. 

As far as inspiring and motivating other women, I encourage women to be their authentic selves and trust themselves. I empower my team members to step into their strengths and give them opportunities to show their skill sets, all while giving them a bit of a stretch to keep learning and growing.

 

Adding in your uniqueness only enhances what you bring to the table. Hone your craft and blaze your own trail.”

 

What advice do you have for the next generation of women in tech?

I encourage other women going into the tech space to be fearless, confident and authentic. Confidence matched with skill is a pretty powerful pairing and can take you almost anywhere. 

Adding in your uniqueness only enhances what you bring to the table. Hone your craft and blaze your own trail. You already have the power to be what you want to be; don't let anyone get in the way of that.

 

 

The QuotaPath team
QuotaPath

 

Sara Strope
Chief Marketing Officer • QuotaPath

QuotaPath offers a compensation solution for sales representatives. 

 

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

Don’t wait to be asked. Take an opportunity and build around it. You’ll be surprised, no matter the size and scale of the company, about how much room there is for growth and change if you take the lead. 

I learned this lesson at an early startup where I was initially brought in to lead customer success. Within a year, I had led a shift in product strategy and taken over managing a line of business. To win these opportunities, I had to share insights derived from customer conversations and a vision that was grounded in our business goals.

Later on, I discovered similar opportunities at IBM, where an overarching business focus on our SaaS products allowed me to create our first customer marketing program and teams. We broadened the scope of IBM’s marketing beyond customer acquisition to customer retention and expansion. Not only did this help overall revenue growth, but it also allowed us as marketers to expand our relationships with product and customer success.

 

How do you stay motivated as a leader, and how do you inspire other women at QuotaPath?

While I definitely keep up with some industry newsletters — such as CB Insights, First Round Review, Product Habits, OpenView, Not Boring, TermSheet — and I love being part of networks like CMO Coffee Talk, I find that taking a step outside can be most helpful to staying inspired.  I’m an avid triathlete and I use my long runs and rides to reflect and recharge. I also love checking out art exhibits for inspiration, even for data-driven decisions! 

For other women who I work with, I love to ask, “What do you want to be known for?” Then, I use that to help make connections, share resources or guide projects. 

I also think it’s really important to celebrate the memorable moments. Small rewards or recognitions can go a long way to reaching your end goal. Believe me, I would never have crossed the finish line of six Ironman races if I hadn’t rewarded myself after hard workouts or training races along the way.

 

If you’re curious, then you’re adaptable and able to change as tech evolves.” 

 

What advice do you have for the next generation of women in tech?

Stay curious. I think the rate of change will only continue to accelerate from tech to policy. Be willing to ask questions of your teammates and customers. 

Try to understand not only how something came to be, but where it could be going, based on your customers’ needs. If you’re curious, then you’re adaptable and able to change as tech evolves. 

 

 

The Orchard team
Orchard

 

Rachel Bennett
Director of Sales Training • Orchard

Orchard helps people buy and sell homes by providing listing preparation, in-house local home advisors, guaranteed cash offers and more. 

 

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

One of the most important lessons that I've learned in my career is that failure is a necessary part of the journey to success. We often think that failure should be avoided at all costs, which causes us to shy away from taking risks, speaking up or trying something new. However, you'll never know how much you can accomplish unless you are willing to take the risk. As Nelson Mandela once said, “I never lose. I either win or I learn.”

Similarly, some things will always be out of your control. It's easy to get frustrated and stuck in a loop of negativity, but this will take you down the wrong path. When you focus on things outside your control, you give up your power to make any significant change or impact. 

Last, help as many people as you can. You'll build a better team, a better environment and, ultimately, a better career. When people can count on you and enjoy working with you, your name will be brought up in rooms you don't even know about, and you'll be given opportunities that you didn't know were possible.

 

How do you stay motivated as a leader, and how do you inspire other women at Orchard?

Starting each day with gratitude and affirmations has been instrumental in staying motivated and inspired. For gratitude, I write three to five things that bring joy at that moment, not just things I'm “supposed” to be grateful for. For affirmations, I write down my intentions as a wife, mom, leader and businesswoman. Some are evergreen statements, while others are goals. By the time I finish writing, I have a clear picture of the incredible life that I already have and what's to come. 

When inspiring the women around me, I'm intentional about communicating clearly and with candor. I'm generous with praise and don't shy away from hard conversations. Feedback is a gift. When you give and accept it openly, people are encouraged to bring their most honest, true selves to the table. 

The most rewarding part of my career has come from the delegation and coaching of my team. I have the honor of leading a team of incredible women. By walking alongside them and providing coaching and mentorship, I have seen them become stronger, more confident and more skilled in their roles. What a gift. I tell them daily that they are the #bestteamever, which is so true.

 

Stop apologizing and downplaying your talents. You bring specific gifts to the table; acknowledge that and be proud of your contributions.”

 

What advice do you have for the next generation of women in tech?

The most important investment that you can ever make is in yourself. Get to know yourself better and work on your personal growth every day. When you know exactly who you are, what you want and what you stand for, it’s easier to confidently walk into a space and take action. 

The Enneagram has been a massively enlightening tool in understanding myself and others in a deeper way. It shines a light on areas of strength and shows where you may be living out unhealthy patterns. 

Similarly, devote yourself to constant education. As cheesy as it sounds, leaders are learners. Read books, listen to podcasts and read articles. Absorb all the wisdom that you can.

Lastly, stop apologizing and downplaying your talents. You bring specific gifts to the table; acknowledge that and be proud of your contributions. As women, we tend to question, self-deprecate and over-apologize. Recognize how awesome, intelligent and gifted you are. Know yourself better, continue to push and learn, and go crush it. 

 

 

Chermaine Hu
Chief Financial Officer and Co-Founder • Episode Six

Episode Six is a payments technology company. Its platform, Tritium, enables clients to transfer any currency including fiat money, cryptocurrencies, brand value points, gold and more. 

 

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

Starting a company is a daunting task, especially in the early stages when resources are limited. The best advice that I was given is that it's crucial to recognize when you need help and not be afraid to ask for it.

Seeking advice from experienced professionals, such as lawyers or accountants, is invaluable in avoiding costly mistakes and saving time and money in the long run. Building a support network of mentors, advisors and other entrepreneurs also provides guidance and support in navigating the challenges of starting and growing a business.

While taking calculated risks is a necessary part of starting and growing a business, it's essential to balance these risks with caution and careful decision-making. Being an entrepreneur requires a mix of confidence, humility and a willingness to seek out and accept help when needed.

 

How do you stay motivated as a leader, and how do you inspire other women at Episode Six?

Staying motivated and inspired as a leader in tech can be challenging, but it's critical to success. I care deeply about each of my team members’ personal and professional growth. I believe the best way to support such growth is by encouraging them to always understand, think and believe. 

Personally, I stay motivated by reminding myself of the impact that our work has on our clients and the broader community while celebrating successes along the way.

To motivate and inspire other women at my company, I try to create a culture of collaboration, openness and inclusivity. I encourage my team to share their ideas and opinions, and I actively listen to their feedback and concerns. I believe in providing opportunities for growth and development through training, mentorship and stretch assignments that allow team members to take on new challenges.

It's also essential to celebrate the successes of team members and to recognize and appreciate their contributions. By highlighting the achievements of other women at our company, we can create a supportive and inspiring environment that motivates everyone to do their best work.

 

Don't be afraid to seek out mentors and supportive networks, both inside and outside of the workplace, that can offer guidance and support.”

 

What advice do you have for the next generation of women in tech?

My advice for the next generation of women in tech is to be confident, persistent and fearless. While we’re seeing more women join fintech companies, I’d love to see more women involved in both the tech and financial aspects of companies, and we need to continue to encourage women’s empowerment.

It's important for you to believe in yourself and your abilities. Don't be afraid to seek out mentors and supportive networks, both inside and outside of the workplace, that can offer guidance and support.

Focus on your factors of success. Use your passion, work ethic and network to help find the right opportunities, and be open to them.

Finally, be prepared to take risks and push boundaries, as this can be key to achieving success and making a significant impact in their field. You should also be willing to learn continuously and stay up to date with the latest trends and technologies.

 

 

The Semrush team
Semrush

 

Olga Andrienko
VP of Brand Marketing • Semrush

Semrush is an online visibility management and content marketing SaaS platform. 

 

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

One of the key lessons that I learned is that you are the one who is responsible for building your career. Don’t wait for somebody else to tell you how to achieve your goals. 

Staying curious is also very important. If you’re curious, you ask questions and those questions help define your career path. I’ve also learned to take initiative, responsibility and ownership of what I do. The more ownership that you take over your projects, the more trust you gain in the company.

 

You are the one who is responsible for building your career. Don’t wait for somebody else to tell you how to achieve your goals.”

 

How do you stay motivated as a leader, and how do you inspire other women at Semrush?

My insatiable curiosity. I try to find interesting aspects in any task and project. I don’t think of myself as an expert in everything. Many people who I work with are great at what they do, and I’m excited about every opportunity to jump into the learner’s seat. 

When it comes to inspiring my team, the majority of them had never met each other in real life before. So in December, we got together offline for the first time. I’m a true believer in a hybrid work environment and we are productive when we work remotely, but nothing strengthens team spirit and builds meaningful connections like meeting each other in person. 

At the end of our workshops, I asked everybody to fill out a Google Form and leave one word for each team member. After that, everyone received a small personal card with all the words from their colleagues printed on it.

This way, everyone got something tangible showing how appreciated they were by their team. While we are scattered around the world, I believe that a physical representation of belonging is something that keeps us motivated.

 

What advice do you have for the next generation of women in tech?

When you start a new job, every task seems exciting because it’s new. With time, as routines creep in, those tasks may become less fun. When this starts happening, that’s the point when you have to intentionally choose your attitude and think about your final goal. 

It’s like learning to surf. You can choose to focus on working toward feeling free and riding the waves one day or you can be frustrated that you keep falling off your surfboard and have to drink salty water sometimes. The decision that you make determines how quickly you make progress. Embrace challenges, as this is what helps you grow as a professional. 

 

 

Jana Shelford
VP, Talent and Culture • Validere

Validere is a measurement, reporting, and verification (MRV) SaaS platform for the energy industry.

 

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

I was once told by a mentor that there’s an invisible line in life. On the line, there is safety. Below the line, there is deflection, blame and insecurities. Above the line, there is curiosity, openness and taking ownership. The key is to not stop moving. Weaving up and down is normal. Ignoring feelings and avoiding conflict will completely limit your growth. Instead, practice placement and fast self-validation to give yourself the control to move. 

The invisible line is a great exercise to check yourself and pivot into solution mode. It has helped me navigate many difficult situations as I have continued to develop my career, especially at the executive level.

 

How do you stay motivated as a leader, and how do you inspire other women at Validere?

I always try to connect with my “why” as a leader, and inspiration really drives me to action. I strive to see the potential in people, and the ability to extract and tap into that area is highly rewarding. Too often we get hung up on proofs of accomplishments instead of the evidence that shows our potential to achieve greatness. That area fuels me. 

I am privileged to be in a role where I can coach individuals, especially women, on a daily basis in this area. Some of my best hires were mothers returning to the workforce with an abundance of transferable skills.

 

Instead of focusing on an exact plan, have a loosely defined career design and focus on the now.”

 

What advice do you have for the next generation of women in tech?

Life is not linear and every chapter is beautiful in its own way. Instead of focusing on an exact plan, have a loosely defined career design and focus on the now. 

Read that book. Execute on a solution. Skip the optional meeting. Attend that seminar. Learn one new skill a day. Ask “why” in that meeting. Go for a walk. Be ruthless with your time and always prioritize learning. 

I call it “well-being calibration.” The spill-over impact on your career development is pretty incredible too.

 

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