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Once Paysafe, Always Paysafe: How an Alumni Community Stays Connected

Writer: Yoana Boyanova
Yoana Boyanova
Sep 29
4 min read

Iliyana Bossashka-Yotova, Senior Reconciliation Systems Engineer
Iliyana Bossashka-Yotova, Senior Reconciliation Systems Engineer

You hold a unique 'boomerang' status, having stepped away from Paysafe to explore other opportunities before ultimately returning. What initially inspired your decision to return, and how did your time away shape your perspective on your professional growth?

What has always stood out to me about Paysafe is the people. The colleagues I worked with, the relationships we built, and the sense of being part of a strong community were a big part of what inspired me to come back.

After many years with Paysafe, I felt I needed to step outside my comfort zone and experience a different environment - to see how other companies work, face new challenges, and gain a different perspective. It turned out to be a truly valuable experience, both professionally and personally.

Most importantly, my time away helped me better understand what I valued in my career and what kind of environment allowed me to do my best work. I came back with a broader experience, a clearer idea of what I wanted for my professional future, and also a renewed appreciation for the people and culture that made Paysafe special to me in the first place.


"The motto 'Once Paysafe, Always Paysafe' strongly reflects the company's culture of long-term relationship building. During your time away from the company, how did being part of the Paysafe Alumni network help you stay connected with the team and the company’s ongoing evolution?

I think it's really special that Paysafe makes an effort to stay connected with former employees. Even after you leave, you still feel part of the community and, more importantly, you feel the relationships you built during your time at Paysafe continue to matter.

For me, staying connected with both former and current colleagues helped me keep a sense of what was happening within the company and how Paysafe was evolving. It also gave me a feeling that, even though I had moved on professionally, I had never completely lost that connection.

I think that is what “Once Paysafe, Always Paysafe” really means - you may leave the company, but the relationships, the people, and the sense of belonging can stay with you.


We know that Paysafe organizes annual closed events specifically to bring its alumni together. Could you share what the atmosphere at these gatherings is like, and why you believe these exclusive events are so valuable for maintaining strong professional and personal bonds?

The atmosphere at these events is always very positive and welcoming. People are open, relaxed, and genuinely happy to see each other again. What I really appreciate is that the conversations are not only about work or professional achievements - we also catch up on what is happening in our lives, share experiences, and reconnect on a personal level.

For me, this is what makes these gatherings so valuable. They help maintain relationships that go beyond the workplace and remind you that you are still part of a community, even if your professional journey has taken you somewhere else. I really value that personal connection, and it makes the idea of “Once Paysafe, Always Paysafe” feel very real.


Paysafe expanded its alumni network to London, further strengthening its global footprint. From your perspective, how does this international expansion of the alumni community benefit former and current employees in terms of knowledge sharing and global networking?

For me, expanding the alumni network internationally is a natural step because Paysafe itself is a global company. We all gain different experiences across markets, teams, and cultures, and bringing people together creates a great opportunity to exchange knowledge and different perspectives. It also helps build connections beyond our local networks, while keeping that shared sense of being part of the Paysafe community.


Returning to a former employer can often feel like stepping back into the familiar, yet the fintech world is constantly evolving. What was the most pleasant surprise or the biggest positive change you noticed about Paysafe’s culture and team dynamics when you walked back through the doors?

I didn’t feel that coming back to Paysafe was a step back – actually, quite the opposite. My time away gave me the opportunity to see how things work outside Paysafe, learn from a different environment, and bring the best of that experience back with me.

At the same time, I was really impressed by how much Paysafe itself had evolved. Many things had changed in how people worked, collaborated, and approached new challenges. So, while I was coming back to a familiar place and familiar people, it also felt like starting a new chapter at Paysafe with my own fresh perspective.


What advice would you give to other women in tech about the importance of 'leaving the door open' when they transition roles, and how they can best leverage alumni networks to support their long-term career journeys?

My advice to women in tech is to own their career journey and never be afraid to explore new opportunities. The tech world is smaller than we think, so don’t close doors - build strong relationships, stay connected, and support other women along the way.

Every experience adds something to who you are as a professional. Moving on doesn’t mean leaving your past behind; sometimes it gives you the confidence, experience, and perspective to come back even stronger. Your past can open doors to your future in ways you may not expect.


 
 
 

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