David Sakamoto: Defining Scalability and Identifying Customer Success Unicorns

David Sakamoto is currently the Vice President of Customer Success at GitLab where he leverages his extensive background to orchestrate customer outcomes while proactively managing customer experiences and aligning teammates, processes, and systems to deliver customer-centric operations.

With 10+ years of experience in customer success and leadership, David brings a wealth of experience, enthusiasm, and dedication to everything he does.

Listen to this episode (or read the transcript below) to learn how David Sakamoto facilitates programs that improve product adoption, actively manage the customer lifecycle, advance solutions via customer advocacy and feedback, and lead renewal and account expansion.

1 Who has been the best manager or leader that you’ve reported to?

I’ve had the opportunity to work with multiple great leaders with one of the most recent being Michael McBride. He’s extremely sharp, very thoughtful, and he cares deeply about his team.

Another great example is the very first manager I had out of college. Mike Doosan really left a mark on me because he was all about supporting my career goals whether that meant within the company or something with another organization. We would have a career conversation every month and it gave me a lot of faith in him and really made me believe that he had my back and cared about what was best for me.

Another leader that I worked with within his organization said something that stuck with me, and it was something along the lines of “your projects and your programs are going to come and go, the legacy you build will be your teams”. I think everybody is going to work with great leaders throughout their career and taking different lessons or practices from these leaders and making them part of your management style is really important.

2 Can you expand on the theory of having your teams be your legacy?

When you look back on your life, you’re not going to remember various deliverables but you’re definitely going to remember the great teams you’ve built. Or you might even remember a teammate that you were able to help through a difficult time. You may have gotten the opportunity to not only help someone get a promotion, but you may have also completely changed the trajectory of your career.

The things that I’m most proud of are the individuals that I helped develop or the teams that I brought together to do great things. When I look back on my career with a very human approach, I’m going to remember the people and the teams I worked with.

3 How do you define scalability when it comes to building teams?

I think scalability is ultimately having the ability to handle a higher level of output while adding more people to the team. When I think about scaling, I often describe it as the platform. In my role, customer success is the platform, but I think it can apply to any role when you’re building a team or building out a platform. I like to think of the platform as a combination of the people, the processes, and the systems and I always start with the people. It’s all about ensuring your team can be successful. I believe that it’s my job to foster an environment that allows my team to succeed.

The second factor is the process. You have to have the right metrics, processes, and systems so you can ensure that your team can be successful both individually and as a part of the organization. You want to make sure your team can collaborate well amongst themselves, your organization, and with your customers and partners. I think of those three constituencies in all situations because they’re ultimately what helps drive results for your customers, team members, and investors.

4 What are some pitfalls that you’ve noticed when building a strategy?

I think the biggest challenge that I see and something I still deal with every day is being able to balance the time you spend on strategy versus tactical work. It can be really difficult to decide how you prioritize your time on a day-to-day basis, so I think the crux is ultimately figuring out how to find the right balance.

It’s important to set time aside every week to check yourself and make sure that you’re balancing your time between all of the different things that are important within your organization while still taking time to step back and be a leader. It’s also about having no ego and not being afraid to admit if you do something wrong. You have to be willing to learn and implement a Kaizen attitude around whatever you’re doing so you can embrace the learning curve and apply your takeaways to future scenarios.

5 How do you plan your time? Do you have any best practices you live by?

I always like to start my week clean, and I don’t like moving into the week and feeling like I’m already behind. I like to clean up anything from the prior week and make sure I set myself up for success for the upcoming week. I tend to plan out my entire week and start with my one-on-ones first thing in the week so I can make sure I’m checking in with my team. When I finish up with that, I like to mix in some team stuff so connecting with our leadership team and attending any functional meetings. Wednesday and Thursday are then generally working days that have all kinds of things woven in. I try to keep Fridays to catch up on anything that was missed because I want to make sure I clean everything up that I set out to do so I can reset my cycle for the upcoming week on Sunday.

I think management is all about cycles so my advice for any leader is to figure out what the cadence is across all of the different durations.

6 Why do you let everybody else speak first?

Not speaking your opinion first is a very minor tactical method that I try to use to really promote servant leadership, empowerment, and autonomy. Looking back, I always had a ton of energy and excitement so I would always throw my opinion in first, but I’ve realized that people process things in different ways and as someone in a management position, I may stifle their perception or steer the conversation a certain way if I offer my opinion first. I want to make sure that I ask everyone what they think before I stifle the conversation with my opinion. 

When you stifle the conversation, you stifle ideas. I think it’s really important to be thoughtful about the fact that everybody processes and engages in conversations differently. You have to be cognisant of your position on the team and thoughtful of the different personalities and their tendencies when it comes to engaging in conversations. As a leader, it’s your job to facilitate the conversation in a way that brings out the best of people’s experiences, passions, and uniqueness.

7 From a hiring perspective, how do you determine if someone will be successful in a customer success role?

Oftentimes you have to be very thoughtful around the skillsets of the individual you’re looking to hire because you need a service person and someone that understands sales and technology. You basically have to build out a profile of the ideal candidate and what you end up doing is building a unicorn. You have to be really thoughtful around what the expectations are for the numerous skills you’re looking for.

I also look for their level of passion towards customer service. I look for people that have specific examples of when they went above and beyond to put the customer first and I want to gauge how they feel when they tell me the story. I like to look for someone that can demonstrate those experiences, but they also have to be extremely passionate. I want them to care enough to be passionate and energetic and I also want to gain an understanding of their level of empathy towards the customer.

8 Do you have any tips or resources for managers that are looking to get better at their craft?

One of my main suggestions would be to not expect perfection. You’re going to make mistakes and your whole team knows you’re going to mess up every once in a while. What’s important is how you guide your team while remaining transparent and letting them know that you’re willing to leave your ego at the door.

In terms of resources, there are a couple of books that aren’t necessarily related to management that I really like. When your business is growing quickly you have to adapt and learn what your role is within the organization and one really great book that pertains to high growth is The Hard Thing About Management by Ben Horowitz. One of my key takeaways from that book was the importance of identifying how you can contribute to the success of your organization as it scales.

My other book recommendation is Never Split the Difference by Chris Boss. It’s about negotiation and it teaches you a lot of core skills with one of the main takeaways being to never split the difference. In order to be happy, both parties need to agree on a true win-win.