Shima Osaka Shows How Advocating for Yourself is Part of Stepping Up

Shima Osaka’s career journey is not a typical one. She was a practicing corporate lawyer, helping to launch Audible’s services for customers in the Asia-Pacific (APAC) region, when she was asked to take on the role of country manager for our Japan service. We chatted with Osaka about that decision, the importance of self-awareness and speaking up in having a fulfilling career, and the exciting things the team in Japan have been working on.

You have a fascinating career journey, from practicing law to being country manager for Japan. How did that come about?

I went to college in Japan, then law school in the US at Columbia University. I took the New York State Bar but started my career in Japan working at a US law firm on mergers and acquisitions and other corporate deals. I did this for about 15 years, then thought, “Is this what I want to do for the rest of my life? Or should I try something new?” I’d been advising companies on international transactions, so I felt confident I could advise a company that wanted to do business in Japan. I found out Audible was looking for legal counsel for APAC and that really excited me. That was in 2015.

Maybe two months into my role, Audible launched its service for Japanese customers, so it was a quick ramp-up. I just absorbed as much as I could and worked closely with my business colleagues on the launch. I also worked closely with Australian law firms to learn their legal landscape, so I could flag potential issues for the Australia and APAC business.

I was surprised by how integrated I was into business issues as well as legal ones, and I was having fun being a part of building something. For my first two years, I was working closely with Matthew Gain, who had been the Australia country manager before he moved into an APAC leadership role. He approached me one day and said something like, “I think you’d be really good on the business side,” and he suggested I challenge myself to step into the Japan country manager position.

It was so encouraging to have the people I was working with believe in me like that—but I really had to think about it. I talked to different people at Audible, and to my family, and they could hear the excitement in my voice when I talked about the role. But I knew it would be a very steep learning curve: everything from putting together a budget, to tracking the monthly metrics, to understanding the various functions and how all the teams interact. As much as I was advising and understanding the business from a legal perspective, being a country manager would require a deep knowledge and experience of all these other areas.

Matthew was my mentor and said, “I’ll help you learn all that.” I watched everything he did. I had a lot of one-on-ones with people around me who said I could reach out any time, like Leanne Cartwright-Bradford, who recently became Head of Operations, APAC, when Matthew moved to a leadership role for our EU marketplaces. I felt like I had a support network that helped me through the transition.

You were country manager for Japan for two years and then you did something pretty awesome, advocating for your success and well-being by asking for time to learn some things critical to your role. Can you describe your thought process around that decision?

I was in the country manager role for about two years, and it was a whirlwind. During that time, we changed from an all-you-can-listen model to a credit model. About a year later, we were still moving forward at full steam, and I realized that to become the leader I knew the business needed, I wanted to dive deeper into specific functions of the business to provide strategic advice. First, I went to the content team to advise them on building a strong pipeline of titles for the Japanese marketplace. I then moved to advise marketing in order to better understand that team. I learned how to build a brand strategy and test it. I worked with customer experience and learned how to encourage more engagement. For about a year and a half I did this sort of tour, exploring all these areas of the business, hands-on, that I couldn’t go deep enough into as country manager. I was really fortunate to be able to do that.

We often talk about career paths at Audible being less of a straight-up ladder and more of a journey with twists and turns and discoveries, like yours. Do you feel like an advocate for this model now?

Yes, because at some point the straight-up ladder ends. This builds more depth in some ways. Audible is great because it encourages that. Who would have thought, 15 years ago starting my career in legal, this would be my path? I’ve enjoyed it. There’s no right path; it’s whatever is right for you. The skills you build along the way will help you in your journey.

Audible’s leadership made an effort to help me find that path, and it prepared me to return to the country manager role in December 2021. It’s been a totally different experience the second time around.

What are some things your team has achieved recently?

The audio entertainment wave has hit Japan these last couple years, and we are thrilled to be able to deliver this to our customers! We moved back to the all-you-can-listen model, with some fresh new content. Already, customers’ reactions have been very positive, so we’re looking forward to celebrating that.

Right now we’re excited about amplifying the strong voices of women, which we’ve done recently in honor of International Women’s Day in March and National Women’s Day in April. We’ve had six female celebrities narrate works by an iconic feminist poet, Noriko Ibaragi. (You can hear a sample, in Japanese, here.) We’re so glad to be able to support female creatives like this.

What do you like to do outside of work?

I love to play sports, so I make sure to get to my tennis lessons! On weekends I watch movies with my kids. I have one who just left for college in New York, and my younger one is in seventh grade. I try to make sure we spend lots of time together because it goes by so quickly.

What are some of your favorite listens?

I recently listened to Momo by Michael Ende (a fantasy novel written in 1973 that's been lauded for its prescience), and just loved how deep the story really is, even though it feels like a children’s story on its face. And Atomic Habits by James Clear reinforces how important it is to make certain lifestyle decisions a habit so that you can continue to be making the right choices for yourself without having to force yourself to do so.