Breaking Barriers: Olga Bortnikova on Women Leading in Tech

Olga Bortnikova’s journey from a traveler to the CEO of Tripsider highlights the power of personalized travel experiences. As a pioneering woman in leadership, she exemplifies the strength and vision women bring to the corporate world. In this interview, she shares her leadership philosophy, the unique challenges and opportunities she faces as a female CEO, and how she supports her team’s growth and success. 

What motivated you to start Tripsider, and what were the key factors that drove you to enter the tech startup space? 

I have always been an avid traveler who meticulously planned my own trips. However, a disappointing vacation in China with a package tour exposed me to numerous issues, including a 5-hour flight delay and an unprofessional tour guide. As I noticed that the tour organizers seemed indifferent to the tourists’ experiences, treating them as mere parts of an assembly line, I realized there was a need for personalized travel services. 

Determined to find a better solution, I discovered that expert-led, small group trips offered a much richer experience, but there was no single platform where travelers could find these tours. Therefore, I decided to create one myself. It was an attractive business proposition, since the adventure travel sector was actively growing — around 15% annually — and expected to be a $2 trillion industry by 2032. Hence, after returning from China, I partnered with two like-minded co-founders, and we invested $10,000 of our own savings into developing and promoting Tripsider, aiming to provide a more tailored and enjoyable travel experience for others. 

How has your vision for Tripsider evolved since its inception, and what role has mentorship played in shaping that vision? 

Adventure travel is the antidote to cheap dopamine. Tackling challenging tasks builds confidence, happiness, and resilience in difficult times. Our core concept has stayed the same since we defined our mission and vision in 2018. Initially, we focused on building a marketplace, but now we’re putting more effort into helping travel experts develop their businesses. This shift has allowed us to create more personalized and high-quality travel experiences. Our mentorship efforts mainly target C-level executives, especially because they handle a lot of data and responsibilities, which is crucial for our growth. 

As a leader, mentoring other leaders often means confronting my own ego. When something goes wrong, it’s important not to jump in and fix things immediately. Mistakes are inevitable, and they provide valuable learning opportunities. By giving people the chance to learn and grow on their own, we foster a more resilient and capable team.

How do you mentor and support your executives to help them grow and succeed within the company? Can you provide an example of a success story?  

In our company, each employee has a Personal Development Plan (PDP) that is supported by C-level leaders from different departments. Everyone has room for growth in areas that might hold them back from achieving their ambitions. Based on these, we create a plan to help our team members set the right goals for their personal and professional development. 

For example, one of our employees, who initially worked with us as a sales manager, expressed a desire to transition into product management. We greatly valued her enthusiasm and commitment to growth, so we decided to support her on this journey. I developed a tailored development plan for her, which included training, mentorship, and hands-on projects to help her gain the necessary skills and experience. 

Even though the shift took four years, now, she works with us as a product manager and is extremely happy with her decision. Her journey is a testament to our commitment to nurturing talent and supporting our team’s professional development. In fact, over the past six months, she has made significant progress and has even started mentoring other employees herself.  

What challenges have you faced as a woman leader in the tech industry, and how have you overcome them to thrive in a male-dominated field? 

As a woman leader in the tech industry, I encountered the same amount of difficulties as males, but they were different. Early on, I learned to establish clear boundaries, which has helped me navigate the typical challenges women face in business. This proactive approach has enabled me to earn respect and trust, allowing me to concentrate on driving innovation and achieving success in a predominantly male field.  

Can you share your insights on how women can navigate and succeed in leadership roles, particularly in industries where they are underrepresented? 

For women aspiring to succeed in leadership roles, especially in male-dominated industries, here are a few key pieces of advice that have helped me: 

Firstly, develop self-confidence. Believing in your abilities and taking on responsibilities is crucial. My background in professional sports instilled this quality in me. It was especially useful during the pandemic when, as CEO, I had to quickly adapt our business strategy. This not only helped us navigate the crisis but also earned me the trust of my team. 

Secondly, trust in your expertise, as well as in other people’s. You don’t need to be an expert in everything, but it’s important to surround yourself with knowledgeable people and trust them. Seeking out mentors is also vital. Consulting with industry experts when hiring for key positions has allowed our company to grow rapidly. Personal mentors have helped me avoid mistakes and plan strategically. 

Thirdly, build professional connections. For me, actively participating in networking events and conferences has opened up many growth opportunities. 

Lastly, maintain a work-life balance. It’s essential to find sources of energy and motivation that help you thrive in your role. Discovering how to recharge is also crucial. 

By following these tips, you can significantly enhance your chances of success in any field. 

What are some key strategies you believe are essential for women leaders to implement in order to build and sustain successful businesses? 

One important strategy is for women leaders to confidently acknowledge their accomplishments. Men often highlight their individual contributions with “I” statements, while women tend to credit their success to teamwork. It’s crucial for women to speak up about their achievements without fearing they’ll be seen as too aggressive. 

Another vital strategy is to be willing to ask for help. Many women hesitate to seek assistance because they worry it might make them seem less independent. However, successful leaders—regardless of gender—know when to leverage other people’s support and expertise. 

Lastly, women should not settle for less than they deserve. While compromise is sometimes necessary, consistently accepting less can hinder long-term success. Successful leaders are often those who stand firm on their principles and negotiate assertively. 

In summary, women can build and sustain successful businesses by confidently owning their achievements, seeking support when needed, and negotiating effectively to achieve their goals. These strategies empower women to overcome challenges and lead their businesses to success.   

What words of inspiration would you like to share with other women aspiring to take on leadership roles in their respective fields?  

Effective and happy personal development relies on two crucial components: a high level of awareness and stable self-esteem. By cultivating awareness, you can accurately evaluate cause-and-effect relationships, as well as formulate and execute actions based on data rather than emotions. Stable self-esteem enables you to feel whole and act according to your goals, rather than simply aiming to win a competition. 

Remember, leadership involves not only leading yourself but also understanding others and the environment in which you operate. Embrace each moment with mindfulness to build meaningful connections and navigate challenges confidently. Your journey to leadership begins with self-awareness and recognizing your potential to create positive change.

Executive Profile

Olga Bortnikova is a seasoned entrepreneur, travel expert, and the co-founder of travel tech startup Tripsider. Under her leadership, the companies have grown into booming platforms with over $30M GMV and more than 500,000 monthly users. Olga is a certified mentor at UN Women and holds an ICF Certified Coach designation.