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Matthew Matsudaira of JimmyJane: “Invest in Diversity”

Invest in Diversity: Diversity is a necessity for any company. Having a diversity-focused culture is more important than ever. At JimmyJane, this has been a focus that has helped me recruit, hire and retain the team that we have built. With diversity comes multiple perspectives, and great ideas will surface. Also, it fosters a culture […]

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Invest in Diversity: Diversity is a necessity for any company. Having a diversity-focused culture is more important than ever. At JimmyJane, this has been a focus that has helped me recruit, hire and retain the team that we have built. With diversity comes multiple perspectives, and great ideas will surface. Also, it fosters a culture that motivates employees to perform at a higher level.


As a part of my series about about how leaders can create a “fantastic work culture”, I had the pleasure of interviewing MatthewMatsudaira.

MatthewMatsudaira is the CEO of JimmyJane and a serial entrepreneur with previous senior leadership positions at Amazon, Chewy, Nordstrom, and numerous startups. He worked on the Chewy acquisition to PetSmart in 2017 and was a founding member of various lucrative Amazon launches, including Prime Now and Amazon Fire Phone. He was awarded Greekwire’s Entrepreneur of the Year, Techcocktail’s Hottest Startup, Retail Edition of XBIZ Honors’ Chief Exec of the Year, and SIGN Magazine’s Chief Executive of the Year — being one of the largest worldwide industry publications.


Thank you so much for doing this with us! Can you tell us a story about what brought you to this specific career path?

My career path has been far from linear. I grew up in Bellevue, Washington, just east of Seattle. After graduating from the University of Washington, I started at Nordstrom, working my way from the stockroom in Women’s Shoes, to Athletic Shoe buyer, to Regional Merchandiser. I was fortunate to learn the brick-and-mortar business from one of the best retailers in the world and leaving my corporate role at Nordstrom was not easy. After much consideration, I took a leap of faith with a startup, Thriva, a provider of online database management software. This decision proved to be a pivotal one, kick-starting my lifelong entrepreneurial journey.

After selling Thriva to The Active Network, I spent some time as an angel investor and eventually founded a company called Wishpot. This early social commerce platform allowed consumers to shop products and services within social media platforms like Facebook and Twitter. After raising a few rounds of funding, the company sold to Lockerz. I then founded Adorii, a daily deal site for everything bridal. This sold to MyWedDeal, owner of The Knot, the largest global wedding site. These back-to-back exits were both exhilarating and exhausting. I wanted to decompress, so I took some time off to travel the world and decide what I wanted to do next.

When I returned, I accepted an opportunity at Amazon, which I consider the next pivotal point in my career. Amazon allowed me to stretch myself intellectually, leveraging my entrepreneurial experience to grow startups and build products within their ecosystem. I thrived in the Amazon culture, where I had the chance to network with some of the most talented people I know. It was incredible to work on forward-thinking, ground-breaking projects. As part of the founding team of Prime Now, I honestly did not think I would ever leave the company. However, when I was offered an executive opportunity at a disruptive eCommerce pet company, Chewy, I could not pass it up. Six months into the role, we sold Chewy to Petsmart, making it the largest acquisition of an eCommerce business at the time. As a serial risk-taker, it was such a rewarding experience to be a part of.

After Chewy, I followed my passion of immersing myself in new industries and businesses. I was able to leverage my experience to consult in the financial and investment world, working with the best private equity firms, investment banks, and hedge funds. This is what ultimately led me to my current role as CEO of Diamond Products, parent of JimmyJane, where I have been disrupting the sexual health and wellness space for close to three years.

Can you share the most interesting story that happened to you since you began leading your company?

My first trade show in the sexual wellness industry was quite the experience. Coming from Amazon, a widget is a widget, so I was sure I was prepared for everything. It was still a bit surreal as I surveyed the products, wondering how I went from selling pet food to sex toys. I learned quickly that this was a space with its own nuances and I had to make sure I understood those well before I could be a disruptor. In my opinion, the industry has a lot of opportunity to catch up to the efficiencies of other consumer goods verticals. This is what I love about leading this company. I can be a pacesetter for how this industry moves forward, while making sexual wellness more accessible to consumers.

Are you working on any exciting projects now? How do you think that will help people?

We always have new initiatives and projects that we are working on. While leading JimmyJane, I have the opportunity to think big and change the trajectory of the company. Companies that are not innovating are the ones that find themselves in trouble. All of JimmyJane’s projects are focused on enhancing the customer experience. Our loyal JimmyJane customers love our innovative, luxe, and great quality products and all our projects are concentrated on the end consumer. JimmyJane’s team is working hard to understand what brings consumers pleasure, to learn how to help deepen the connection with their partners, and to provide joy and sexual well-being, especially during this pandemic.

Ok, lets jump to the main part of our interview. According to this study cited in Forbes, more than half of the US workforce is unhappy. Why do you think that number is so high?

More than ever, I believe that people don’t leave companies because of work or compensation. Employees are more likely to leave a company because of their leaders. I know of too many people who have left roles because they do not feel supported by their management. When companies are only focused on the bottom line and do not consider their team their greatest asset, it leaves employees feeling disconnected and uninspired. JimmyJane’s leadership principles are living, breathing embodiments of how our employees can expect to be treated. They are the guardrails that keep the company focused on success and are referred to consistently throughout the day. During our recruitment and interview process, we actively seek leaders who embody these traits. The team that we have retained and hired has helped us cultivate and maintain a great company culture, one where we set the bar high, but ensure we support our team to continue to achieve greatness.

Based on your experience or research, how do you think an unhappy workforce will impact a) company productivity b) company profitability c) and employee health and wellbeing?

An unhappy workforce causes the quality of work to suffer at every level of the organization. A disconnected workforce will not be focused on constantly seeking the practices that drive the company forward. This slows productivity and has a significant impact on the financial performance of the company. Most importantly, the employees’ health suffers, both mentally and physically. Employees stop caring and putting effort into moving the company forward. To create and maintain a happy and healthy culture, it is the leadership’s responsibility to manage it daily. In all of my roles, it was important for me to authentically engage and communicate with my employees. Regardless of the size of the organization, I strive to know all of my employee’s names, their goals, passions and challenges. This lets my team know that I care and that I am truly invested in their personal success.

Can you share 5 things that managers and executives should be doing to improve their company work culture? Can you give a personal story or example for each?

Define the Company Culture and Principles: Many companies operate with no company values or principles. Setting the company values and principles was one of the first things I did when I took over as CEO. Having clearly defined principles are fundamental to your culture and the success of your company. These should not be a set of words printed on the wall in your office. They need to be ingrained in your employees’ fabric, the decisions you make as a company and leader, and you must consistently talk about it with your employees. JimmyJane’s leadership principles guide us in making hiring decisions and help us make strategic decisions for the business. For example, one of our leadership principles is “Crave Curiosity”. We actively encourage our team to seek ideas that interest them, even if the benefit is not immediately apparent. This gives our team the freedom to explore ways to make us better and encourages innovation.

Promote Collaboration: I have seen company cultures shift focus from high-performing individual contributors to more of an emphasis on teams. With the pandemic and our team working remotely worldwide, we must promote and provide tools for our employees to collaborate on projects together. I can no longer walk down the hall and interact with my employees. Instead, we get creative by utilizing tools like Zoom, Teams, text messages, Monday (project management platform), and phone calls to stay connected and feel the company’s pulse. Collaboration tools like Zoom allow me to have working sessions with my employees that feel more personal. We use Teams to communicate in real-time without having to send an email. In my opinion, by having the right collaboration and communication tools, a company can raise productivity by 25% — 35%.

Communication: In most companies, communication flows downward from the leadership team to the rest of the employees. This type of communication stifles employees who want a voice to drive change. At JimmyJane, everyone is always talking and communicating with each other. I like to ask my employees questions like, “Do you think this is a good idea? How do you suggest that we do it differently? What is your opinion or view on this project?” I value my team’s opinion, and I have always surrounded myself with smart and talented people who I can learn from.

Invest in Diversity: Diversity is a necessity for any company. Having a diversity-focused culture is more important than ever. At JimmyJane, this has been a focus that has helped me recruit, hire and retain the team that we have built. With diversity comes multiple perspectives, and great ideas will surface. Also, it fosters a culture that motivates employees to perform at a higher level.

Engage Employees through Recognition, Appreciation, and Rewards: When you have employees who are not engaged or do not believe in the company’s vision, they are less productive. Get your employees engaged. They will be more productive, happier and drive better results. At JimmyJane, we try to recognize our employees often and consistently. The recognition or appreciation is as simple as a high-five or thumbs up emoji or a handwritten letter from their manager. Simple gestures go a long way with your employees and can boost morale. Most importantly, it signals to your team that you care.

It’s very nice to suggest ideas, but it seems like we have to “change the culture regarding work culture”. What can we do as a society to make a broader change in the US workforce’s work culture?

As a society, we need to shift the top-down culture that stifles creativity and prevents individuals from feeling they can truly make a difference. The hierarchical approach in the US work culture can leave more junior employees feeling out of touch with senior management and fearful of sharing ideas. By recognizing the value of contributions of the entire team, regardless of title, it ensures that we do not fall behind when it comes to more progressive thinking being advanced. Great ideas can come from every level of the organization and we need to promote a work environment that embraces diversity of thought.

How would you describe your leadership or management style? Can you give us a few examples?

My management style is a unique blend of visionary, pacesetting, and servant leadership. Visionary leadership often can be inspirational, charismatic, strategic, or authoritative and I feel that I embody those traits. I provide a clear vision for JimmyJane, so the company is moving towards common goals. Pacesetting means that I’m out in front and leading the team in the direction I want us to move. This increases productivity and encourages healthy competition. When I first arrived at JimmyJane, the company was too comfortable in its way of doing things. Having a pacesetting leadership elevated the company’s performance and enabled us to accomplish historical results. My servant leadership style focuses on the mentorship and coaching aspect of leadership. I enjoy supporting my team to grow professionally and personally.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

For me, my parents are the people who helped me achieve my success. They instilled the values and work ethic that allowed me to overcome obstacles and uncertainties. My parents provided me the support to allow me to follow my dreams, but they let me stumble along the way and did not always pick me up. They taught me grit. For as long as I can remember, I have always been competitive, and my parents held me accountable and responsible for my own success. How does this translate to my career? I believe that my team would say that I am pushing us to be better every day. I have learned to handle setbacks and be resilient. I have an underdog mentality, and I always want to prove our critics wrong. Why not me? Why not you? Be ambitious to reach for success at every opportunity.

How have you used your success to bring goodness to the world?

One of my investors told me, “pay it forward with mentorship when you make it big.” Being an entrepreneur, or even a senior leader, can be lonely at times. You need another perspective or someone supportive of your success. I have been committed to helping others achieve their dreams — taking action on that idea, from students in college classes to entrepreneurs thinking about starting a company. I want to be able to contribute to their success and cheer them on along the way. It is a great feeling when you can mentor someone and help them solve issues they encounter at work or running their company. Additionally, I feel like I’m continually learning from my mentees.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

I am a collector of quotes and mantras and look to them for inspiration and perspective. My mantra for 2021 is “How you do anything is how you do everything.” It comes down to your consistency in thoughts and actions. Take personal responsibility. Everything you do makes a mark and leads you closer or further away from your goals. At JimmyJane, there is so much to do, and I ask my team to get better every day and learn from our wins and losses. If you believe in your team and trust the process, you have a consistent path to success.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

While there are a variety of inequities I would like to solve, the movement that I believe would bring the most good right now is to eradicate COVID and help the millions of people affected by it. Not only are people grieving from losing loved ones, but they are also hurting from losing jobs. I am contributing to food banks to help those that need that support get back on their feet and I would like to see this become a global movement. If communities share resources with those who are losing everything, it will help minimize the impact of this pandemic. The faster that we can defeat COVID and help those who are struggling, the quicker the economy can recover. This is not a US issue; it is a global issue, and everyone needs to contribute to the fight.

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