Speaking to Le Wagon Tokyo fresh graduates during Career Week, Paul Roberts reflected on the changes he has witnessed and the lessons that have remained surprisingly constant.
“The market changes all the time,” he said. “But one thing never changes: getting that first opportunity is the hardest part.”
Paul’s website and Linkedin
There is no single Japanese tech market
Over the course of his career, Roberts has recruited for a wide variety of organizations. He has seen the rise of Japan’s startup ecosystem, periods of rapid hiring, economic downturns, and more recently, the arrival of AI-powered development tools.
Those experiences have taught him that there is no such thing as a single Japanese tech market.
A candidate with fluent Japanese, several years of experience, and permanent residency will encounter a completely different landscape from a recent Le Wagon bootcamp graduate looking for a first engineering role. Likewise, startups, global technology firms, and traditional Japanese corporations often look for very different qualities when hiring.
Understanding these differences is often more important than trying to follow generic career advice.
First job matters more than the perfect job
One pattern Paul has observed repeatedly is that many job seekers become overly focused on landing a dream role.
The reality, he argues, is that careers are rarely built in a straight line.
Some of the strongest candidates he has worked with started in contract roles. Others began in technical support, quality assurance, freelance projects, or internships before moving into software engineering.
The common factor wasn’t the title of their first job. It was that they gained experience.
Once employers can see evidence of professional work, even for a relatively short period, entirely new opportunities begin to appear.
“The first role opens the door to the second role,” said Paul (we absolutely agree!).
The hidden value of conversations
While many job seekers spend countless hours submitting online applications, Paul believes some of the most important opportunities happen away from job boards.
Throughout the session, he encouraged Le Wagon Tokyo students to attend meetups, networking events, and industry gatherings.
After decades in recruitment, he has learned that careers often develop through unexpected connections. A conversation with another engineer, a startup founder, or even another job seeker can eventually lead to introductions and opportunities that would never appear through a standard application process.
For people who feel uncomfortable networking, his advice was straightforward: start small and stay curious. Go with a friend if that will help you feel more comfortable.
The goal isn’t to ask everyone for a job. It’s to meet people and become part of the community.
AI changes the tools, not the fundamentals
No discussion about technology careers in 2026 would be complete without mentioning AI.
Paul acknowledged that the way software is built is changing rapidly. Developers increasingly use AI tools to write code, accelerate workflows, and solve problems.
But despite the excitement surrounding new technology, he believes the fundamentals remain largely unchanged.
Companies still need people who can communicate effectively, work collaboratively, learn quickly, and solve real business problems.
The tools may evolve, but the qualities that make someone successful in a team remain remarkably consistent.
A career is a long-term project
Looking back on more than two decades in Japan, Paul’s perspective on careers is notably patient.
Job searches can be frustrating. Rejections happen. Hiring markets fluctuate. Economic conditions change.
Yet he encouraged students not to judge themselves against someone else’s timeline.
Careers are built gradually. Skills accumulate over years. Networks expand one conversation at a time.
For aspiring developers preparing to enter Japan’s tech industry, Paul’s message was ultimately optimistic. The path may not be predictable, but opportunities continue to exist for those willing to stay flexible, keep learning, and remain engaged with the people around them.
After 25 years of watching careers unfold, he has seen enough success stories to know that the first step is rarely the most glamorous one.
It’s simply the one that gets you started.
Got questions about building your tech career in Japan? Book a call with our bootcamp manager to discuss your goals, career prospects, and how Le Wagon can help you get there.
