How I Develop New Leaders in Customer Success

Ben Rosenberg
VP of Sending Experience
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Interview Highlights:

  • Building connections is critically important for new leaders
  • Exhibit leadership behaviors and qualities even before you have the formal title
  • Leadership is about being able to navigate different circumstances with different leadership styles.

Can you please introduce yourself and what you do?

My name is Ben Rosenberg. I’m the Vice President of Sending Experience at Sendoso. 

My role consists of a few primary areas. First, I’m responsible for our Customer Support function, which helps customers with both technical and platform questions, as well as shipping and logistics. 

Second, I’m responsible for our vendor strategy. That’s working with the vendors across our platform that we sell products directly through, as well as vendors that we help customers source items for their own sending. 

Then the last part of my role right now is program and project management across the Sending Organization. That’s all things supply and logistics. 

How did you learn to be an effective leader?

Like many others, I started my professional career doing retail and restaurant-type jobs. My first real exposure to a leadership role was in a retail setting. There wasn’t a whole lot of leadership development or training available in that role, so it was a lot of learning as you go. I made mistakes and took advice along the way. 

Most of my early formal leadership development took place at Charles Schwab, which is a large brokerage and bank. They have a pretty robust leadership development program, and there’s a lot of investment and commitment to training across the company. 

My path in that company was fairly typical for a contact center. I started off as an individual contributor and moved into a team lead role. I did manager rotations across different teams to help out, and then finally moved into a formal leadership role. At that point, my career started to be a mix of direct leadership roles and project work. 

Then I jumped over to startup land, where I was able to take some pretty big steps in terms of the size and scope of my organization based on some of the leadership skills I had acquired.

One of the things I like to tell folks who I mentor is that one of the potential positives of working in a smaller startup company is that you have the opportunity to step into some roles that may or may not be available to you in a larger organization. 

I definitely benefited from that. From there, I found myself gravitating towards being passionate about leadership in a lot of different capacities.

What leadership challenges do startups often encounter?

It’s very typical for someone to start in a smaller company or startup as a really good CSM. And then all of a sudden, they’re the manager of the CSM team because the company has hired their second or third CSM and your original CSM becomes the de facto leader. That’s a mistake many companies make, not just startups. 

From my perspective, being a great individual contributor and being a leader are very different careers, trajectories, and skill sets. I try to be very deliberate with my team when it comes to building career paths for folks that want to be individual contributors, versus a career path for leadership. 

Another challenge related to the first is that people are put into positions that they’re not necessarily equipped for. They need guidance to really operate effectively, and the realities of working in a startup mean that oftentimes the rest of the leadership team doesn’t have the bandwidth - or even the experience themselves - to develop these young leaders. 

So one of the things I try to preach that I wish I would’ve done earlier in my career is to do what the Catalyst Coaching Corner does, which is build a connection with strong leaders from other organizations. Those types of resources and relationships become so critical as an employee at a younger company that may not have the ability or resources to dedicate as much as they’d like towards leadership development. 

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How do you know when someone is ready to be promoted?

The first step of jumping into that leadership role is exhibiting those behaviors and qualities, even though you may not have the formal title. I look for an ability to effectively collaborate and communicate with their team. Are they looked at as a de facto leader amongst their peers? These are the “tickets to entry” in my mind before we can go any further into potential conversations. 

The next category that I look at is their decision-making. I don’t expect someone to move into a role like that and make the right decision every single time. It’s more about, can they think through questions, issues and challenges in a way that is rational and logical? Can they articulate it? Do they have a good understanding of the potential risks to the business of their decision?

I would be very unlikely to be upset about someone’s decision if they can justify how they came to it. I also don’t want leaders who shoot from the hip and make snap judgments. It’s like I always preach to my newer leaders: I would much rather you ask another leader, someone else in the company, or reach out to me in order to talk through a new situation or challenge. I would define it as humility or understanding that they’re going to encounter situations that they may not know how to navigate. 

How do you guide someone who is already in a leadership position but doesn’t have the necessary skills?

The way I would phrase it is that a great leader is not someone who’s really good at one particular leadership style. You can think of it as arrows in your quiver. You should have the ability to coach different people in different ways, depending on their learning and development style to manage different circumstances, team personalities, attributes, or business goals and objectives. 

I would suggest that these new leaders go out to folks they’ve either worked with in the past or other leaders in the company, and ask them for their opinions on how to handle a situation. Better yet, go talk to someone who has a leadership style that is way outside of your comfort zone. While that may not be something that you gravitate towards, there are probably aspects of what that person does that you can pick out and make work for yourself. In doing so, you round out your abilities and become able to approach different team types and coaching situations. There is no single “right” way to be a great leader, in my opinion the best leaders are the most adaptable 

What quality helps new leaders the most?

A willingness to learn. You have to approach a role like that with a desire to understand what works and what doesn’t. What do other people do? How can you learn from their experience?

When I was a little younger, I used to be of the opinion that experience wasn’t that big of a deal. If you were smart and have hustle, there’s not much to be gained from the length of time you’ve been a leader. 

But now that I’m a little further in my career, I’ve realized that that’s so far from the truth. It’s the ability to approach a new role with a mindset of learning that’s most important, while drawing on your past experiences in similar situations.

Another really important aspect of successful leadership is that you don’t have to be right all the time. Your team’s not going to necessarily expect that from you, oftentimes it’s about trusting the team you’ve put in place, and championing their opinion even if you don’t necessarily agree.


Sendoso, the leading Sending Platform, helps companies stand out by giving them new ways to engage with customers throughout the buyer’s journey. By integrating digital and physical sending strategies, companies can increase the effectiveness of their existing go-to-market programs and improve their relationships with customers. Trusted by over 800 companies, Sendoso is an essential part of successful demand generation, account-based, and customer experience programs.

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