Why does Strategic Customer Success Manager Kengo Lei Kobayashi love being a part of Dropbox Japan? He shares his story, his goals, and his perfect WFH lunch recipe with us

Life Inside Dropbox
6 min readOct 7, 2020


In Japan, a country chock-full of tech companies vying for talent, some job seekers may have a tough time finding the right fit for them. Such is not the case for Strategic Customer Success Manager Kengo Lei Kobayashi, who joined our team remotely this spring, and has since proclaimed himself one of Dropbox’s biggest fans. We caught up with Kengo and learned all about his journey to Dropbox, why he loves working on our team, and how working from home has been going for him.

Left: Tea time in Asia (Singapore); Right: Coffee time in US (San Francisco)

What is your role at Dropbox?

I’m a Strategic Customer Success Manager whose role is leading the DX (Digital Transformation) shift for enterprise customers. My mission is to change their mindset to see that Dropbox is a must-have tool, not just a nice-to-have tool.

Can you tell us a little about your journey to Dropbox?

When a recruiter first approached me in February, I had been working in Singapore. But after Singapore was locked down due to the COVID-19, I was evacuated to Taiwan, which is my wife’s home country. At that time, various travel stipulations forced me to stay in Taiwan. However, I was able to continue the hiring process from my Taiwanese home because Dropbox didn’t care where I was. Even though other competitors asked me to visit their Tokyo office for the final interview, Dropbox didn’t ask me to do that. I felt that they cared about my health as their first priority, even though it’s an important meeting.

Singapore pre-lockdown

I’ve since moved back to Japan, and all the hiring processes were very comfortable because most of the document work could be done online. Signing the offer letter? Done by HelloSign from my home! Background check? Done by the BGC system from my home! A lot of document tasks? Done by Dropbox Paper communication, with kind support from HR members!

Can you tell us about something at Dropbox that you’ve been part of that you’re particularly proud of?

I’m proud of working with our current APJ members. Everybody brings their professionalism and high-level skill sets to the table. Even though it’s hard to retain customers due to COVID-19, our team is still succeeding in growing our business, thanks to strong teamwork and collaboration. In fact, this quarter, APJ has the highest customer renewal rates globally within Dropbox. It’s such an amazing result that we can be proud of. I’m happy and grateful to work with such great team members every day!

Group photo taken pre-lockdown

How have you been challenged at work recently?

Every day at Dropbox is challenging for me, but the biggest challenge I’m facing now is the full-time WFH situation. Erasing the commute time from my daily life really improved my quality of life. However, since I’m a new hire, it’s also been challenging. Because I’ve never met my customers, boss, or colleagues, and I’ve never even visited my office! Catching up on the corporate culture and making deeper relationships via virtual communication is much more difficult than on-site. It requires more strategic communication, with a deeper understanding of which technology can help with each issue.

What is one thing that’s exciting you about work right now?

Currently, I’m part of a user event project named CAB (Customer Advisory Board). It’s an exciting global project that requires cross-regional and cross-functional collaboration. Team members are coming from the Marketing team, the CSM team, and the Architect Team, and they’re also coming from San Francisco, New York, Tokyo, Sydney, etc. Even though I’m living in Japan, I feel that I’m one of the members of this global business, and I’m representing the Japanese market!

What’s your favorite thing about your role at Dropbox?

One of the reasons why I decided to join Dropbox and why I love it is the diversity. Most of the time, Japanese branches of global companies localize too much for our business culture and easily lose the diversity. However, Dropbox is different. Even as the Japanese branch has grown, they’ve still kept the same concept of diversity as they do at HQ. One good example of this is that when I decided to take paternity leave for my first baby (who will be delivered end of 2020), nobody gave me any negative response. In Japanese culture, this is so unusual and surprising! Dropbox really keeps the same philosophy globally.

Where’s the first place you want to travel when quarantine is over?

Absolutely HQ, located in San Francisco! My onboarding program was supposed to be held there, but it was canceled due to COVID-19. I really want to visit to feel our culture and meet my colleagues who are working there.

Singaporean food
Left: Simple Japanese lunch; Middle & right: Taiwanese food

What’s your go-to WFH lunch?

My routine WFH lunch menu is quick, cost effective, and healthy :)

  • Brown rice
  • Natto(fermented soybeans)
  • Raw egg
  • Kimchi
  • Instant miso soup

What’s your favorite thing about working from home?

No commute time! In Japan, taking the crowed train is one of the biggest sources of stress. So avoiding this uncomfortable time helps us all have more healthy lives, both physically and mentally. We also get to be with family all the time. My pregnant wife needs more support for daily things like moving heavy stuff or doing house work, and because of WFH, it’s possible for me to help her with these things between meetings.

Kengo and his family at his master degree graduation ceremony (MBA)

What would you want prospective new team members to know about working at Dropbox?

Dropbox values their culture so much. They treat employees very well, and all the team members are supportive and collaborative. They take “customer success” seriously. It’s a truly global company where you’ll find the same diversity and fairness in place regardless of where you are working. It’s the best place to work if you want to establish your career in the global tech industry!

Interested in learning more about Dropbox Japan, or our other locations across the world? You can find more information and job postings here.



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