The latest issue of Think Global People magazine is out now!

---

“During Soviet Union occupation, no one was allowed to be an entrepreneur. Everybody was equally poor. Today, Estonia has more unicorn companies per capita than any country in the world,” she says. “But back then, it was a very different country.”In 1994, the last Russian troops withdrew from Estonia, formally ending the occupation. This marked the conclusion of more than five decades of foreign domination and the beginning of Estonia's journey as a nation that regained its full sovereignty. Today, Estonia is a thriving democracy, a poster child for digital governance, and a member of the European Union and NATO.“After the Soviet Union collapsed my father, who had been an electrical engineer, became an entrepreneur building swimming pools and selling furniture, and my mother became a social entrepreneur who pressed for change,” Karoli explains.She credits her parents’ entrepreneurial spirit for her own journey from teenage inventor and later with her brother the founding of Jobbatical, which today is an immigration and relocation platform that combines deep immigration expertise with advanced technology to make it simpler for businesses to move employees from one country to another.“During the Soviet occupation, you couldn't travel, you couldn't have ideas, and yet my parents somehow managed to keep an open mind and really see that everything is possible,” she says.

Karoli’s entrepreneurial turning point

A remarkable moment came in Karoli’s life when she was a 16-year-old and had an idea for an invention which won a school competition. She came up with the concept of a reflector for pedestrians and her father urged her to take out a patent for the invention.“My father could have told me, ‘You’re just a girl. Forget about your ideas.’ But instead, he encouraged me,” she says. “That moment made me realise you don’t have to be from a top university or wealthy to create change.”She then became officially the youngest inventor in Estonia and her story was recently published in the US children’s book “Kid-ventors: 35 Real Kids and their Amazing Inventions” side by side by with inventors like Benjamin Franklin.  At just 23, she became the youngest CEO of MTV in the world, building the brand’s presence in Estonia. Later, she expanded National Geographic and Fox International channels across the Baltics. Yet despite her growing professional portfolio, she never forgot the thrill of creating a business of her own.Her turning point came during her time at Singularity University, a think tank funded by NASA and Google. Immersed in Silicon Valley’s culture of innovation, Karoli asked herself: Why do the world’s brightest minds flock here? Why can’t similar innovation happen in other parts of the globe?“During the three months I was there, I began to ask how one region in the world was creating so many industry-changing companies,” she explains. I realised that people are not born smarter in Silicon Valley, it is that smart people circle the globe and move regions to go and build those companies. So I thought we should inspire to them to go to places like Tallinn, Stockholm, and Amsterdam as well.”

The creation of an international jobs platform

The answer came in the form of Jobbatical, a platform she founded with her younger brother to connect skilled talent with global opportunities. Initially conceived as a way to merge work and exploration, Jobbatical became a cross-border recruitment platform. It inspired professionals to dream of living and working in cities like Tokyo or Stockholm.“My brother and I are very different,” she says. “I am the outgoing one who likes to inspire people, lead teams and come up with the vision. He is the one who makes things work. He takes care and doesn’t like to take risks.”As the company grew, Karoli noticed an unexpected bottleneck in the form of immigration. Employers struggled to navigate outdated visa systems, and this logistical hurdle meant that although Jobbatical could find the right people, clients often saw a long delay in getting the candidates through the permits and permissions required in order to start work.Then in 2019, Karoli made the bold decision to pivot Jobbatical’s focus entirely to immigration and relocation services.“It was hard to make the decision and at first it felt like we had failed,” she admits. “We had spent years building something great, only to put it aside. But the data was clear— immigration and work permits were the pain point we needed to solve.”The decision was not easy. It meant laying off a third of her team and convincing investors to back an entirely new direction.“I was really nervous about presenting the new direction of Jobbatical to investors, but they supported me because the data showed we need to pivot and my vision for the company’s future was clear.”The pivot proved transformational. Jobbatical streamlined immigration processes for companies worldwide, combining technology and expertise to remove barriers for international hires. Today, the company is a leader in its field, and Karoli’s decision to pivot has paid off.

The value of mentors

As the founder and CEO of a rapidly growing company, Karoli is no stranger to the sacrifices and challenges that come with running a business.“Being a CEO can be incredibly isolating,” she says. Despite having a robust team and supportive investors, she emphasises that leadership at the top can be a real challenge.“You can’t burden your family with work problems, and you can’t be fully vulnerable with your team. That’s why having an executive coach changed my life—it gave me someone to talk to, someone who could help me grow not just as a leader, but as a person.”Through her work with her coach and her personal development, she has learned to be more comfortable with her role as female entrepreneur and start-up leader.“When I got accepted to Singularity University, I kept thinking, ‘Maybe they made a mistake.’ I looked around at the doctors, engineers, and other accomplished people and felt like I didn’t belong. But over time, I realised those thoughts were holding me back. Women, especially, tend to doubt their value—something we need to challenge in ourselves and each other.”She also credits her mentor Patty McCord, the former Chief People Officer of Netflix, who is now a Jobbatical board member, with providing her support and advice just before Jobbatical’s business pivot, especially around messaging.“We met when we were both speaking at a conference, and I asked for advice on how to pivot in a way that would empower people who build this new business,” Karoli explains. “She really supported me and talked me through the whole communication plan. I am really grateful to her, because the pivot was so successful that I remember three months later Union Square Ventures, our investor, said that this was the most extraordinary pivot they had witnessed. I also learned that it is OK for ask for help and that although change is hard, you can do it in a way that is positive.”

Redefining the workplace with fully remote teams

Karoli’s leadership style reflects her belief in transparency and trust. Jobbatical has been a remote-first company since long before the pandemic made it a trend, and she views flexibility as a core part of the company’s success.“Even before lockdown we were all working remotely, and last year, we gave up our headquarters because no one was using it. It had become this symbolic space, like an old photo album collecting dust. Instead, we focus on bringing the team together for summits or quarterly meetups in different locations.”Her team spans 26 nationalities across five continents. This diversity is a strategic advantage because she can employ the best people wherever they live and whatever time zone they operate in. Managing such a distributed workforce does have challenges, which is why Karoli encourages a culture of transparency and responsibility.“I treat my team like adults. That means sharing financial data, strategic plans, and even the hard truths,” she says. “People are shocked by how much information we share, but I believe it empowers them to make better decisions. Knowledge can be heavy, but it’s also liberating.”

Overcoming gender bias in business and investment

As one of the first female entrepreneurs in Estonia to raise venture capital, Karoli has first hand experience of the gender biases that persist in business.“Last year, only 2% of Venture Capital funding in Europe went to women,” she says. “It is like giving boys 99 candies to open a candy store and giving girls one candy, then wondering why the boys are more successful.”Her experiences have led her to conclude that the industry often focuses on coaching women, rather than addressing systemic biases.“Women don’t need to be fixed. The problem lies in the questions we are asked, the opportunities we are given—or not given—and the ingrained biases we face. That is where change is needed.”Still, she sees her own journey as part of a larger movement to empower women to set up and run their own companies.“When I raised funding, there were barely any female founders in Estonia doing the same. Now, there are so many incredible women starting companies.”Beyond her business achievements, Karoli’s legacy includes co-creating the world’s first digital nomad visa.“When I pitched the idea in 2016 to then Estonian President Kaljulaid, it sounded crazy but now over 60 countries have adopted it,” she says.

Balancing business and motherhood

As a mother to an 12-year-old daughter, Karoli doesn’t shy away from the complexities of balancing work and family.“My daughter has travelled with me since she was one. She’s attended kindergartens in Singapore and Malaysia, and now she’s dividing her time between the UK and Tallinn.“She has seen what’s possible. I hope it inspires her to dream big and to know that her ideas can make a difference. That’s the most important lesson I have learned—every child should know they can change the world.”

Resilience and adaptability in a changing world

Karoli’s journey is a testament to courage and adaptability. Her advice to aspiring entrepreneurs? “Ask for help. People want to help you. And don’t let fear hold you back. Hard things can be done right.”She also stresses the importance of resilience and having mentors.“Resilience is like a muscle,” she says. “You train it by pushing through adversity. But it is not just about enduring; it is about clarity—being convinced of your vision and adapting without losing sight of your mission.”An example of this is when the pandemic brought Jobbatical’s operations to a halt. Countries closed borders, travel ceased, and global uncertainty reigned. It was a test of resilience that would make or break her company. Despite external pressure, Karoli made the strategic decision to stick with her expansion plans.“Everybody was laying off staff, shutting down new markets, and pausing expansion,” she recalls. “But I went against the grain. I knew if we abandoned new countries like Germany and Spain, we would lose our ability to scale when the markets reopened.”The strategy paid off. By 2021, Jobbatical had not only survived but doubled its revenue. Her team’s quick pivot to create scalable, flexible technology also set the company apart, enabling them to reopen markets rapidly when borders eased.Her vision now for Jobbatical is to make moving to a new country as easy as booking a flight. She regards the processes that dominate global mobility today as outdated and bureaucratic, describing them as relics of a bygone era.“The passport system, as it exists, is a century-old concept. It is biased and inefficient. We have the technology to create something better—a digital passport that prioritises skills and needs over birthplace,” she says.She firmly believes such innovations could democratise opportunity. By reducing the friction of relocation, she has a vision for a world where talent flows freely, unhindered by outdated systems.

The importance of global experience

Karoli credits international experiences for shaping her worldview and fostering creativity and believes in the transformative power of cross-border mobility, not just for individuals but for societies.“When I was 17, I lived in the United States as an exchange student,” she says. “Six months in, I realised how profoundly I had changed. If more people experienced life abroad, the world would be a better place. Travel opens your mind, and science shows it makes us more creative. It is a lesson I have carried throughout my life.“The more we understand each other, the less room there is for fear and division. If I could change one thing, I would make international exchange a compulsory part of education. It would reduce the divisions between people and the fear and ignorance that fuels extremism.”

A seamless platform for mobility

Karoli believes that the shift in global mobility is just beginning, and that while legacy providers have dominated for decades, technology is enabling a new wave of solutions.“At Jobbatical, we’re putting the individual at the centre of the process, reducing friction and creating a seamless experience,” she says. “With data and technology, we can create a system that is fairer and more effective, matching talent with opportunity, regardless of nationality.”

---

View Think Global Women’s Outstanding Global Women page

---

---

Find out more about the Think Global People and Think Women community and events.

---

Subscribe to Relocate Extra, our monthly newsletter, to get all the latest international assignments and global mobility news.Relocate’s new Global Mobility Toolkit provides free information, practical advice and support for HR, global mobility managers and global teams operating overseas.

©2025 Re:locate magazine, published by Profile Locations, Spray Hill, Hastings Road, Lamberhurst, Kent TN3 8JB. All rights reserved. This publication (or any part thereof) may not be reproduced in any form without the prior written permission of Profile Locations. Profile Locations accepts no liability for the accuracy of the contents or any opinions expressed herein.