It inspired professionals to dream of living and working in cities like Tokyo or Stockholm. As the company grew, Karoli


noticed an unexpected bottleneck in the form of immigration. Employers struggled to navigate outdated visa systems, and this meant


logistical hurdle 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. So in 2019, Karoli made the


bold decision to pivot Jobbatical’s focus entirely to immigration and relocation services. 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. 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. She also credits her mentor, who


is now a Jobbatical board member, with providing her support and advice


just before Jobbatical’s


business pivot, especially around messaging.


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.


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 & 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. “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, it sounded crazy but now over 60 countries have adopted it,” she says.


BALANCING BUSINESS & MOTHERHOOD As a mother to an 11-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


“ 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.”


7


RESILIENCE & ADAPTABILITY IN A CHANGING WORLD “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.” 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 prioritises skills and needs


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.


that over


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.”


THINK GLOBAL WOMEN


GLOBAL LEADERSHIP


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