A brutal company survey revealed that someone wrote, "I don't want to work with Gina." For Gina Kim, employee number 4 at eShares (now Carta), this feedback was devastating—but it became the catalyst that transformed her into a leader who would help scale the company from startup to an 8-billion-dollar valuation with 1,000 employees.
Kim spent a decade in Silicon Valley, building customer success teams from the ground up and helping startups navigate the treacherous waters of growth. Her journey from operations manager to leadership expert wasn't smooth—it was marked by painful feedback, difficult customers, and the constant pressure of startup life.
In this candid interview, Kim shares the hard-won lessons about leadership that most founders learn too late: why taking on the toughest job is the only way to earn respect, how employee happiness directly translates to customer success, and why even the most experienced leaders never stop learning from everyone around them.
Watch the full interview now on EO's YouTube channel! Below is the complete transcription of the interview. Minor edits have been made for clarity and readability.
Key Highlights:
"You know, as a leader, you might think, oh, I've been there, I've done that. I know everything. You don't know everything. You never know when you're gonna need help. You don't know when you're gonna fail. You are still going to learn from everyone."
"In a way, for you to be a better leader, you need to course correct right away. Unless you make that correction as soon as possible, it could be like a decision that fails your startup."
"So the reason why a leader should take on the toughest job is because that's the only way you'll get the respect of your team, especially at a startup."
"One thing I believe is that employee happiness equals customer happiness because when the customer success employee is happy, that feeling will transfer over to the customer and they will try to do more than what they have to do."
"Now, I would say my KPI is when I get that look on the founder's face that they have the aha moment."
"In a way, for you to be a better leader, you need to course correct right away. Unless you make that correction as soon as possible, it could be like a decision that fails your startup."
"So the reason why a leader should take on the toughest job is because that's the only way you'll get the respect of your team, especially at a startup."
"One thing I believe is that employee happiness equals customer happiness because when the customer success employee is happy, that feeling will transfer over to the customer and they will try to do more than what they have to do."
"Now, I would say my KPI is when I get that look on the founder's face that they have the aha moment."
When Brutal Feedback Became a Leadership Wake-Up Call
Can you tell us about your journey at eShares and how you built the customer success team from the ground up?
Gina Kim: Hi, my name is Gina Kim, and I worked in Silicon Valley for about 10 years. I started out as employee number 4 at eShares, as an operations manager, and I also helped with customer support, customer success, and I built that team from ground up. By the time I left, eShares was 8 billion in terms of evaluation. We had about 1000 employees. What I focused on is helping startups grow in terms of customer journey and go-to-market strategy and helping them also with just growing their customers.
I think this was back in 2016 when eShares was still growing. One feedback that I got was actually from Henry, and he said that in a company survey someone wrote, 'I don't want to work with Gina.' And I really thought of it. And at first it was very hurtful because as employee number 4 I thought, OK, I'm doing my best to make eShares successful. Why is it that this person is not feeling that I'm doing that?
And I thought back to the things that I did and I looked at my Slack messages and I realized communication is a problem. We were getting to the point where we were bigger and certain messages that I was sending to the product team seemed like I was ordering them what to do using my influence as employee number 4.
I think this was back in 2016 when eShares was still growing. One feedback that I got was actually from Henry, and he said that in a company survey someone wrote, 'I don't want to work with Gina.' And I really thought of it. And at first it was very hurtful because as employee number 4 I thought, OK, I'm doing my best to make eShares successful. Why is it that this person is not feeling that I'm doing that?
And I thought back to the things that I did and I looked at my Slack messages and I realized communication is a problem. We were getting to the point where we were bigger and certain messages that I was sending to the product team seemed like I was ordering them what to do using my influence as employee number 4.
The Humbling Truth About Leadership
How did that feedback change your approach to leadership and working with teams?
Gina Kim: That's when I realized, OK, I shouldn't take any of these human relationships for granted because success is not permanent. You never know when you're going to need help. You don't know when you're gonna fail. You know, as a leader, you might think, oh, I've been there, I've done that. I know everything. You don't know everything. You are still going to learn from everyone.
You get a new intern that came in straight out of college. There's something that you are going to learn from that person because I think a lot of founders, yeah, they think that OK, even if they made a mistake, they kind of have to go with their own vision and keep going the wrong path. But when you think about it, everyone already knows that the mistake has been made.
In a way for you to be a better leader, you need to course correct right away. Unless you make that correction as soon as possible, it could be like a decision that fails your startup. You never know. Some people might have really great solutions, but they might not be telling you because they're introvert or because they're scared to speak up and by creating this collaborative environment, you might actually have a better result.
You get a new intern that came in straight out of college. There's something that you are going to learn from that person because I think a lot of founders, yeah, they think that OK, even if they made a mistake, they kind of have to go with their own vision and keep going the wrong path. But when you think about it, everyone already knows that the mistake has been made.
In a way for you to be a better leader, you need to course correct right away. Unless you make that correction as soon as possible, it could be like a decision that fails your startup. You never know. Some people might have really great solutions, but they might not be telling you because they're introvert or because they're scared to speak up and by creating this collaborative environment, you might actually have a better result.
Why Leaders Must Do the Hardest Job
What did you learn about the role of a leader in taking on difficult tasks and earning team respect?
Gina Kim: One thing that I learned at Carta is that as a manager, you're the one who's doing the toughest job. So, at Carta, what we would say is when you get promoted, people don't say congratulations. They say, 'I feel sorry for you.' So the reason why a leader should take on the toughest job is because that's the only way you'll get the respect of your team, especially at a startup.
If you're just directing your team members to do what's needed, they'll do literally just 100% of what they need to do. But at a startup, you really, everyone needs to put in 120%. And so that motivation factor is so important.
Another thing that's really important is that as a leader, you're there to unblock the problems that your team has. If the team is working on something and they're hitting some kind of roadblock, in a way, you have the hardest job because you're doing things that might be very difficult for the team to do. At Carta what I did was when we have very difficult customers, I was the one who was talking to them and I'm the one who's sort of apologizing to them. That's really helpful for the other team members to see. Then they realized, oh wait, Gina is there to really take care of me. It's not about just asking me to do things that are impossible.
If you're just directing your team members to do what's needed, they'll do literally just 100% of what they need to do. But at a startup, you really, everyone needs to put in 120%. And so that motivation factor is so important.
Another thing that's really important is that as a leader, you're there to unblock the problems that your team has. If the team is working on something and they're hitting some kind of roadblock, in a way, you have the hardest job because you're doing things that might be very difficult for the team to do. At Carta what I did was when we have very difficult customers, I was the one who was talking to them and I'm the one who's sort of apologizing to them. That's really helpful for the other team members to see. Then they realized, oh wait, Gina is there to really take care of me. It's not about just asking me to do things that are impossible.
The Connection Between Employee and Customer Happiness
How do you approach building genuine connections with your team members and what's your leadership philosophy?
Gina Kim: For me, my leadership style, I listen to the people I work with and I want to have that genuine connection with them. I don't want to say I know everything and you need to do it my way. Even as a customer success leader, I want during my one-on-one with my team members, I ask them what is it that you want to do ultimately? And if they want to be an engineer or if they want to be a data analyst, I want to help them do that. They could do it through an internal transfer or it could be by just going to another company, but at the end of the day, people are going to do what they want to do. And so for you, if you help them get there, it's actually good for the startup.
One thing I believe is that employee happiness equals customer happiness because when the customer success employee is happy, that feeling will transfer over to the customer and they will try to do more than what they have to do. So as a leader, you're not going to be able to see what the employee is doing all the time. You have to trust them. The only way to know that is by being a good leader and motivating them and truly caring for them and having that genuine connection with that employee.
One thing I believe is that employee happiness equals customer happiness because when the customer success employee is happy, that feeling will transfer over to the customer and they will try to do more than what they have to do. So as a leader, you're not going to be able to see what the employee is doing all the time. You have to trust them. The only way to know that is by being a good leader and motivating them and truly caring for them and having that genuine connection with that employee.
The Sports Team Approach to Leadership
You mentioned that Carta was run like a sports team. Can you elaborate on that philosophy and how it shaped your approach to coaching?
Gina Kim: One thing that I really loved about Carta is that it was run like a sports team. The managers were considered more of a coach, and when you look at a sports team, the overall goal of the team is to win, right? As a sports team, the coach is there to really help the team understand what they did wrong, and then they'll improve it so that they can win for the next time.
Having that kind of coach in your personal life is, I think, also very helpful because that coach can help you get to the right path and they're not just creating this path for their sake, but it's for you. They're helping you go to that unique path.
So I didn't have an actual personal coach until 2 years ago. Before that, I used a lot of people that were in my life as sort of my coach. One informal coach I had, I would say would be Henry. Even when he was giving me negative feedback, he was very gentle about it and gave me the reasons why, which I think is very important. I also had another informal coach, this lady that I work with, and she is right now in her 70s and she's gone through a lot and she was a single mother. She actually encouraged me to come to California.
You don't have to have a coach who's super successful or anything like that, but someone who is genuine that you can talk to that really cares for you, I think it's really important. One thing I noticed is that when people talk to coach, if you don't agree something then you don't agree and then you come to terms and find the best approach. I think that's really important.
Having that kind of coach in your personal life is, I think, also very helpful because that coach can help you get to the right path and they're not just creating this path for their sake, but it's for you. They're helping you go to that unique path.
So I didn't have an actual personal coach until 2 years ago. Before that, I used a lot of people that were in my life as sort of my coach. One informal coach I had, I would say would be Henry. Even when he was giving me negative feedback, he was very gentle about it and gave me the reasons why, which I think is very important. I also had another informal coach, this lady that I work with, and she is right now in her 70s and she's gone through a lot and she was a single mother. She actually encouraged me to come to California.
You don't have to have a coach who's super successful or anything like that, but someone who is genuine that you can talk to that really cares for you, I think it's really important. One thing I noticed is that when people talk to coach, if you don't agree something then you don't agree and then you come to terms and find the best approach. I think that's really important.
The Aha Moment That Defines Success
What drives you now in your work with startups, and how do you measure success in helping founders?
Gina Kim: What my customers would tell me is that they want to focus on the product and they don't want to deal with issuing stock options or dealing with investors and the fact that now this was all done by Carta was really helpful for them. Because they're able to use their time more effectively. And those are the types of moments where it's just so rewarding.
Now, I would say my KPI is when I get that look on the founder's face that they have the aha moment. And it's actually helping them grow and become a better company and helping their employees be happier and help them create a better work environment and I want to do that for a lot of the startups that are not in Silicon Valley because they don't have all the resources that Silicon Valley startups have. So if I can bring that to them, that will give me joy.
Now, I would say my KPI is when I get that look on the founder's face that they have the aha moment. And it's actually helping them grow and become a better company and helping their employees be happier and help them create a better work environment and I want to do that for a lot of the startups that are not in Silicon Valley because they don't have all the resources that Silicon Valley startups have. So if I can bring that to them, that will give me joy.
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