Customer success is one of the hottest departments to work in right now according to numerous reports, so why is there a lack of representation? And why does customer success struggle to be part of the conversations that drive the business forward?

In this article, I’ll share three reasons why this might be the case, with advice on how to overcome each obstacle and reposition CS from a cost-center to a strategic and invaluable department.  

My name is Gemma Cipriani-Espineira, I am Vice President of Customer Success at Chili Piper, where I also lead the customer support team.

In this article, I hope to provide value from some of the things I've learned having been a VP at two different software companies reporting directly to a CEO.

Chili Piper

Chili Piper is a software that makes meetings happen. We have the most advanced routing and scheduling tools out there.

My background

My history has been spent the last 10 years in SaaS companies. I've worked in different industries. I started off at an entry-level sales development role for a public relations and marketing software company called Vocus and worked my way up there to an account director position.

They were then acquired by Cision and at the time I was hired in by referral to another company called Decibel, which at the time, was a bootstrap startup.

I did very well with Decibel growing the team from zero to a team of 25 with a global remit looking after enterprise customers and was able to move across to Boston, which is where I'm based now.

Chili Piper happens to be a fully distributed company so I'm still working globally with people supporting customers around the world.

Getting a seat at the table

This topic, in particular, getting a seat at the table, I don't think we talk about enough in customer success. I don't know why that is, I think it might be because, in customer success, we're very helpful people and maybe too busy focusing on the jobs we have to do for our customers that we don't focus enough or advocate on our own careers.

I'm excited to be talking about it and I'm not just going to be sharing my learnings, I'm also going to be sharing things some of my peers have shared with me through recent conversations, on a webinar series called Chief Customer Officer Secrets that I've just launched.

A definition

Let's jump right into it and talk about the definition of a seat at the table. For me, a seat at the table can mean many things. But one of the things that always springs to mind is the Solange album, one of the greatest albums of all time, in my opinion, A Seat at the Table.

Solange, A Seat at the Table

In customer success, having a seat at the table means you are part of the conversations that drive the business forward.

If you're reading and you work in customer success at whatever level and you don't have that seat at the table, you might feel angry and you're right to feel angry. But I'm going to share some of the reasons why there is a lack of representation and what you can do about it.

Why is there a lack of representation?

There are lots of reports out there that say customer success is one of the hottest markets to work in and I agree with these reports. But when you look at the jobs available - this is just a quick LinkedIn search I did yesterday - there are over 100,000 customer success manager jobs out there which is pretty phenomenal.

Why is there a lack of representation?

Then you look at VP of Customer Success, and you can see just under 2,000 jobs. That's a 2% representation at an executive level.

For Chief Customer Officer (CCO), which is the highest position you can get to in customer success, there are only 21 results that came back. Most of them were VP of Sales roles, only a handful actually had the proper chief customer officer title.

This proves we're a growing industry, but we don't necessarily have the same seat at the table other departments do.

It just doesn't really add up.

That doesn't add up – calculator

Here's one of the reasons why it doesn't add up.

CS is still relatively new

CS is still relatively new, it sounds pretty obvious but we have to think about how new this industry is.

I love this example here because it shows the transition from listening to music on CDs to listening to your subscription on Spotify. That was only a recent switch.


Best Buy, which is one of the largest electronic retailers in the US, only stopped selling CDs in 2018, we're not talking that long ago.

It was only then at around the same time that we saw the big companies like Adobe and Microsoft changed from traditional software models to subscription-based models.

They were the first ones to really bring in customer success as a department because with a subscription, it's easier for customers to switch and you have to prove value to retain reoccurring revenue.

But because we're still a new industry, there are some truths, there are some things we have to act on to get a seat at the table.


Be great at the function you grew up in and advocate for professional growth within CS

The first thing is just to be great at the function you grew up in. It's unlikely as a child, you said "I want to be in customer success", and you dedicated your education and your initial experience to doing so. That's okay, that's normal.

Be great at what you grew up in, and advocate for professional growth within CS. So if you're part of a customer success team at the moment, and you don't have a growth plan in front of you, work with whoever's leading the team to build that plan, to understand what the skills and competencies are to progress in the profession.

Report into the CEO - set priorities and make them happen

If you can, find a business that has customer success reporting directly to the CEO, this is easier said than done. I've been fortunate to have worked in businesses that have this.

But even if you're not reporting directly to the CEO, you can set priorities and make them happen and share them back with the CEO.

That's really our job as the closest people to the customer, to share knowledge with the highest executive in the business.

Example priority: customer onboarding

An example of a priority you can set and focus on would be customer onboarding. So how long is it taking you to onboard customers?

At Chili Piper we decided to double down on the number of days it takes to onboard customers and we have made that priority happen. We focus all our resources on improving that. That's been extremely well received by the board and the executive team.

Get experience out of the customer success function or find ways to collaborate

The last thing is to try to get experience outside of the CS function or find ways to collaborate with other teams. Customer success doesn't happen in isolation, it's a way of doing business.

So understanding how other parts of the business work is incredibly valuable. If you can't afford to have a stint in product or marketing or sales or engineering, perhaps you can find different projects you can collaborate with those teams on.

People don’t understand customer success

The second truth is people don't understand customer success. I've already talked about it being quite a new thing and acknowledging that truth, but it's new and therefore it's not fully understood.

I like to think Siri is a good measure of how well people understand things and I asked her yesterday, do you understand customer success? She wasn't able to help out.

People don't understand customer success


Set a CS mission to avoid becoming “the everything department”

With this in mind, the things you can do to help get a seat at the table is to set a very specific mission for the customer success team you're in to avoid becoming that everything department.

We're absolutely pulled in a million different directions by our customers and by the different demands we have from the rest of the business. So setting a mission is so powerful because when the going gets tough, you can always come back to that mission, and use that mission to prioritize the things you're really going to focus on.

Once you have that mission, getting the rest of the company to understand it is equally as important. At Chili Piper, we've set a very clear mission for the customer success and support team, which is to grow and retain happy, active users.

It clearly defines what we're here to do and everything that we do supports that mission.

Continuously educate others, internally and externally, on the role and importance of customer success

Secondly, continuously educate others, both internally and externally. Let's not forget that externally, we're working in a new industry so there's a very strong collegiate environment in the industry.

And you can reach out to people and collaborate on blogs, talks, attending events like the Customer Success Festival - a great example of how you can educate others on what customer success means for your business as well.

Make time for strategic thinking - look at the entire business and focus customer success on solving the most important problems preventing growth

Making time for strategic thinking sounds like something pretty obvious but it's extremely important. If you're working in customer success, and you've got a customer demand coming in, you're going to prioritize working on that no matter what.

But you have to find a way to create time to stop, pause, reflect, understand how you're achieving the expected outcomes you wanted to achieve since the last time you took a pause for strategic thinking.

This part is really important - identify what the most important problems are for the business, not just for your customer. An example could be you know there's this nuance in the product that's really frustrating some customers but you have to be able to prioritize working on bigger problems if they exist outside of that nuance.

For instance, if your sales team is not selling to a particular industry or a particular market, maybe you're going to have to pause and go and help sales with that go-to-market plan. I always like to think the biggest customer you can have in your portfolio is your sales team. That's another piece of advice I'm going to talk about.

Strategic thinking is more than just about you and your function. It's about what the business needs to grow and how you can help the business.

Customer success ROI is hard to prove

The last truth that has come up often in conversations with others about why customer success doesn't have a seat at the table is that customer success ROI is actually quite difficult to prove.

I love this meme because this concept of 'money please' comes from the fact that a lot of customer success teams have spun out of traditional customer support or client services teams.

Parks and Recreation, Mona-Lisa Saperstein

Those kinds of teams have always been viewed as a cost center rather than a profit and loss department, which is there to actually make money for the business.


Work closely with sales leaders to design revenue

So in order to work around that ROI hurdle, work really closely with sales. I said it earlier but if you can work with sales closely, you can find a way to design revenue that is going to be better for the growth of the business.

An example would be taking all of the knowledge you have about your customers, the wins, the anecdotes, the things that aren't working for them, and continuously feeding that back to sales leadership. Most salespeople don't want to sell the wrong things to the wrong people.

They care about their reputation, and they want to do what's best for the customer. Our job is to allow them to do that.

Measure the impact of customer advocacy

The second thing is such an easy, quick win and I wish more people did it. Measuring the impact of customer advocacy can really go a long way in getting a seat at the table.

Customer advocacy can mean many different things but it's basically all of the good stuff you do with your customers. We spend a lot of time talking about the bad stuff, what are the churn reasons? What can we do to avoid them? But we need to spend just as much time talking about the good stuff.

That could come from case studies, references, testimonials, reviews on G2. It could come from creating a user conference and getting a certain number of customers to speak at that conference, or to speak at other conferences for you.

Measure the amount of things your team is doing, and set some targets, set some incentives behind it. Because you can tie back these things to revenue, particularly where there's a direct correlation between a new customer being won based on a case study or reference.

But you can also tie it back to the metric of lifetime value, which is a very important lagging outcome that all boards care about. So measuring the impacts of customer advocacy is extremely powerful.

Share revenue-based targets for gross and net retention

Lastly, finding a way to share revenue-based targets is going to allow you to enter that conversation that helps drive the business forward. This can be difficult for many, particularly if you're not responsible for what I like to call the paperwork side of things.

So if you're not the customer success team who is selling the renewal, who is creating the upsell or cross-sell paperwork, is doing any kind of account management function, then how do you say I'm willing to share this net retention target?

Well, you have to do it. Ultimately, customers don't renew and don't buy more if they're not achieving the outcome. So you have to have a great relationship with whoever's responsible for the paperwork if you're not, and you have to work with them to design revenue, but also have some skin in the game.

Be behind that net retention number. If you're in customer success, and you can't speak to the growth retention or net retention numbers of your business, then you definitely will have a problem getting a seat at the table.

I hope that this provided value to all of you.

Thank you.