At Railsware, we love sharing updates with our community—but we also love a good chat with each other. That’s why we have a tradition of virtual coffee chats—a chance to meet people from different fields, hear their stories, and talk about more than just work.
Lately, we’ve been inspired by our teammates’ career change experiences. And, of course, it wouldn’t be Railsware if we didn’t share those stories with you.
So, in our series #CoffeeWithRW: Career switch, we invite you to grab a coffee and join us for real talk about career shifts, lessons learned, and unexpected turns along the way.
Career switch: from Head of sales to recruitment. Wins, tips, biggest mistakes

They say change is all about growth. But what if that change means completely shifting careers and going from a leadership role to starting over as an intern?
And it happened – I abandoned my position as a Head of Sales for a fresh start.
It was fresh in many senses: new industry, new role, my first international experience, and also my first work online.
Now add this: I changed careers while on maternity leave. It wasn’t easy, but it was absolutely worth it.
If you’re wondering what the reasons for my choice were, how I made the idea come to life, or what was my biggest mistake – grab a coffee or tea and keep reading. Here’s the story behind it all.
Archeology, herring, and management major
The switch story took place almost a decade ago. But let’s start it even earlier. Believe it or not, my childhood dream job was one that involved as little interaction with people as possible. For instance, to become an archeologist. A lab, a library, or an archive—those were my ideal workplaces. My younger self found comfort in quiet, solitary spaces and imagined a future built around that.
Meanwhile, my mom, a talented journalist with a broad network in Ukrainian academia, had a different perspective on my career. Since I was twelve, she actively encouraged me to explore the best educational opportunities, introducing me to university presidents and professors. While she wasn’t exactly thrilled about some of my early aspirations—like becoming a fashion designer —her guidance came from a place of care and practicality.
Eventually, I ended up studying management at a trade and economics university. It wasn’t my first choice, but I trusted her instincts and went along with them. The way I was raised and the encouragement to meet high expectations all shaped my early career. There were even jokes growing up that if I didn’t put in the effort, I’d end up selling herrings at a market. Ironically, part of my university program involved practical training at a factory that—you won’t believe it— produced canned herring.
By my fourth or fifth year of university, I had started working in sales. Later, I moved into magazine publishing. Through it all, I stuck to one guiding principle: do your best wherever you are.
Even if the current path wasn’t exactly what I had imagined, I focused on showing up and doing the work to the best of my ability.
From queens back to pawns
I was moving up the ladder in sales, ultimately leading my own team as Head of Sales—a role that felt like a big achievement. Then, something new landed on my plate: hiring new colleagues.
I remember sitting at my desk one day, scrolling through job descriptions, and studying requirements, values, and expectations. To my surprise, I really enjoyed it. One of our main goals was to find high performers—result-driven people. Back then, I didn’t have much hiring experience, so I leaned on books, tests and my own experiments to figure things out. Sometimes, I’d even ask candidates to draw something and analyze what they chose to sketch first.
It was during one of those moments that it hit me:
I could actually get paid to do something I genuinely enjoyed.
During my maternity leave, I found myself in the right moment to act on this realization. With time on my hands and no pressure to rush, I started exploring the possibility of transitioning into recruitment. I didn’t have a solid backup plan—if it didn’t work out, I could always return to my sales career.
Here’s how I approached it:
- Read a lot on psychology, negotiation, and anything that could guide me in this new direction. Back then, online courses weren’t as common, so I relied on books and self-study.
- Focused on improving my English. I’d been learning it since I was five, but most of my sales experience had been on the domestic market. Little did I know, my first job offer would come from the international market:)
- Applied widely and set personal criteria for my next role. Location was a priority—I lived in the suburbs of Kyiv and spent over five hours on a daily commute. So, I looked for remote opportunities or jobs closer to home.
Fun fact: Remote work had always been on my wishlist—long before it was trendy. I used to joke that working remotely felt like something out of sci-fi, a dream where you could teleport instead of commute. When I finally got my first remote job, I loved it, and yes, I fully embraced working in pajamas. It became my favorite “uniform”, and to this day, I still love working in them.
- Throughout this journey, my biggest supporter was myself. I trusted my intuition and leaned on it to guide me through every decision.
- When I started interviewing, I focused on finding a role where the company’s values aligned with mine and where I felt comfortable.
That first offer came from a recruitment agency—for an intern position. The job required strong English and a commitment to mastering their materials in just 15 days. It was an intense crash course: recruitment lingo, CRM systems, business analysis techniques, and strategies—all condensed into two weeks, with a final test to prove I was ready.
The agency’s owner believed sales and recruitment were closely tied. “If you can sell, you can sell a job opportunity,” they said. With my sales background, I felt ready to take on the challenge—and that’s how I swapped my business attire for pajamas and stepped into a new chapter of my career.
Lessons learned
Switching careers is never easy, but some lessons from my experience made the process smoother and helped me grow professionally. Here are a few insights I’d like to share.
1. Be honest with yourself
The first step to any meaningful change is being honest with yourself. I would start with the next questions:
- Am I happy where I am?
- What am I truly looking for—happiness, security, financial stability?
- What’s motivating me to move forward, dream bigger, or make a change?
Once you understand your reasons, it’s time to figure out what’s holding you back:
- Why am I not where I want to be yet?
- Where do I want to go? And what do I need to do to get there?
It’s not always about having a clear childhood dream—those who fulfill them are rare. Most of us are on a journey of exploration, and that’s perfectly okay. The more accomplished you are in what you do, the more positively it affects not just you but everyone around you.
In career changes, emotions always come first.
I grow where I feel comfortable—with myself and those I work with. When there’s harmony, everything else falls into place.
I’ve never wanted to go back. Past roles, like in retail, taught me lessons but also showed me what didn’t fit. Even walking into a supermarket now reminds me why I moved forward.
Now, I’ve found my place, and it feels right.
2. Don’t let fear guide you if it’s not about survival
I’ve learned to face fear by looking at it rationally:
- What’s really holding me back?
- Discomfort with the unknown?
- Doubts about success?
Those feelings are natural, but for me, the regret of not trying was always far greater than the fear itself.
The truth is simple: you either make a change or stay where you are.
You might end up happier, or you might not—but a career shift won’t destroy you.
You might end up happier, or you might not—but a career shift won’t destroy you.
Fear, after all, is a biological defense mechanism that kicks in during truly dangerous situations. So, how life-threatening is this situation for you, really?
3. Listen to yourself above all else
The biggest obstacles often come from others—people who fear change even more than you do. But this is your life, not theirs. Some may justify their opinions as care or concern, even family, but their fears shouldn’t become yours. My advice? Listen to yourself above all else.
Looking back, I’m grateful every single day that I made the leap of faith. Where I am now feels right—I belong here. And every day reaffirms that it was the best decision I could have made.
4. Follow your gut and find the resources you need
There are no limits to resources today—whether it’s learning a language, mastering a tool, or using ChatGPT. These days, it feels like everyone has written something about their field. Finding information isn’t the hard part anymore. The real challenge lies in your curiosity and desire to explore what truly interests you.
When you genuinely enjoy what you do, it’s not just about getting paid. It’s about asking deeper questions—like why a button works the way it does, or why a specific code language is used. The answers are always out there if you care enough to look for them.
Back then, it was helpful to check articles about interviews, books on psychology, and negotiation guides like Never Split the Difference [ a book on mastering negotiations to gain influence and drive results].
Knowledge, after all, doesn’t weigh you down—it’s a tool you can take anywhere and use in any situation. So feed your mind with quality materials ( not fluff like “How to break into the field in a month).
5. Stay with a team where you can grow
One of my biggest mistakes during my career switch was staying too long in a company where I had no room left to grow. My gut told me to leave, but I hesitated because the team was great. When the team changed, so did everything else, and I finally left. No regrets—it was a lesson learned.
Whether you’re switching fields or not, remember: you deserve to work where you can grow, feel valued, and be inspired. Now, I’m in a place where I truly belong. I work with people who challenge me, amaze me with their solutions, and push me to keep growing every day. Growth starts with the right people.
How it changed my personal life
A major career shift inevitably changes you. You adapt to new people, values, and ways of working. For me, working across cultures has taught me to be more open-minded. When I read The Culture Map [a book on how culture influences your own international collaboration.], it all felt so familiar—I’d seen those differences firsthand. If I had read it before gaining this experience, I would have seen it more as fiction.
This experience also taught me patience and when to let things go. It’s something I’ve carried into my personal life, improving how I communicate with family and approach everyday challenges. It’s been a shift in more ways than one.
Want to change? Do it or do it scared!
I hope my experience has inspired someone—whether it’s to embrace transformation or to take a courageous step forward. In any case, you are the master of your own life, and it’s all in your hands.
As for some useful resources:
The books:
- Neil Gaiman – Norse Mythology
- The Lucifer Effect: Understanding How Good People Turn Evil
The series:
- La Casa de Papel / Money Heist
The movie:
- I Origins
The psychological board game:
- “Keys to the World of Emotions”
