In this episode of Mastering CS: Candid Leader Insights, Irina Cismas sits down with Mark Rocklin, Director of Success Management EMEA at CloudShare, a platform that helps software companies run virtual labs for product demos, training, and technical enablement. Mark came from the pre-sales side before finding his home in customer success, and six years later he is still managing some of the same customers he started with.
He shares how CS and operations work together at CloudShare, why responding to every NPS score made a bigger difference than any system they implemented, what breaks first as a CS team scales, and how he thinks about building a CS organization from the ground up with just three people.
What You’ll Learn
- How customer success and account management differ and where they overlap
- What a director of success management actually does on a day-to-day basis
- Why CS and revenue operations sit under the same function at CloudShare
- How CS acts as the connective tissue between sales, legal, finance, and product
- What operational process has made the biggest difference as the team has scaled
- Why negative NPS scores are Mark’s favorite to receive
- What breaks first when a hands-on CS approach meets rapid growth
- What Mark looks for first when building a CS organization from scratch
Key Insights & Takeaways
- CS is the nucleus of the business. In SaaS companies, customer success is the outward-facing function that connects product, sales, and operations. It feeds insights back into the business while driving revenue through land and expand.
- People come before process, and process before systems. The right people with the right process will make any system work. The wrong people will break even the best one.
- Responding to every NPS score builds trust. Customers are often surprised when someone actually responds. That simple act of engagement goes further than almost any other touchpoint.
- Negative NPS scores are an opportunity. Turning a negative experience into a positive one is where CS earns its place. That’s the challenge worth chasing.
- Automation should preserve personality, not replace it. As teams scale, the goal is to automate the tedious operational tasks while keeping the human touch in every customer interaction.
- High achievers who aren’t culture fits don’t last. Overachievers who undermine team cohesion might deliver short-term results but damage the long-term foundation. Culture fit outlasts performance metrics.
- Leadership, CSM, and rev ops is the founding trio. If you’re starting a CS organization with three people, you need someone on the ground with customers, someone keeping the data clean, and someone driving the strategic vision.
Podcast Transcript
Intro
Irina (0:03 – 0:28)
Welcome to Mastering CS Candid Leader Insights, the podcast where we dive into the world of customer success with industry leaders. I’m your host Irina Cismas and today I’m joined by Mark Rocklin, Director of Success Management EMEA at CloudShare, a platform that helps software companies run virtual labs for product demos, training and technical enablement. Mark, I’m really happy to have you here, thanks for joining!
Mark (0:28 – 0:29)
Thank you for having me.
From Pre-Sales to Customer Success: How It Actually Feels Different
Irina (0:30 – 0:40)
You came from the sales side. How different does customer success actually feel compared to account management?
Mark (0:41 – 2:35)
It’s a great question. And my background actually, it’s interesting, my background originally did come from the pre-sale side, which I enjoy, but it gave me a sales and relationships and building relationships. But it wasn’t something that I thoroughly enjoyed as much as when I moved into the customer success and account management field.
For me, it’s about building lasting relationships. It’s about providing value. It’s about the buzzword of being a trusted advisor.
I like to just call it more of a friend. I mean, the customers I work with end up becoming true friends of mine. I’ve been at CloudShare for over six years now and have had the same customers for the better part of six years.
The difference between customer success and account management is a really, really interesting one. There’s a lot of overlap. Some might say that there’s no overlap at all, that it’s the same position called something different.
The thing that I’ve seen mainly in the industry is that customer success typically won’t hold the book of business in terms of renewals, upsells, and expansions, and things like that. Whereas account management will be responsible for that. So account management will be responsible for the money and customer success is more associated with adoption.
But I’ve seen a lot of overlap in that. So it really kind of depends on the company that you go to and the way they define the position because many times you’ll see someone as an account manager in one company and they’re doing the exact same thing as a customer success manager in a different company.
What a Director of Success Management Actually Does Day to Day
Irina (2:37 – 2:58)
I do have some curiosities coming from your sales background, but I’m going to leave them for later on in the conversation because I want to ask you, what does your week actually look like as a director of success management for EMEA at CloudShare?
Mark (2:59 – 5:01)
Yes, so it’s an interesting role. So we’ve been growing a lot and as we’ve been growing our roles have expanded into kind of dual functionalities. So I manage the customer success team as well.
So on a day-to-day basis, I actually do still hold a book of business of my own as well. I have my own customers, ones that I’ve had for many, many years. And we keep that relationship because that’s very important to us.
For us, the relationship is key when it comes to providing value, when it comes to maintaining trust with our customers. So I’m still hands-on. So on a day-to-day basis, you will see me hands-on and it actually helps.
I like being on the ground level, working with customers day-to-day, working through issues, providing value because it also helps me on that high-level side where I’m also now involved in strategic discussions of what does this customer success team look like? Where are we going in the future? What are some of the strategies that we want to implement?
And what comes along with that is cross department functionalities as well. So working with pre-sales team, working with rev ops team, working with finance, working with HR. So I have a lot of responsibilities in that realm, specifically within the EMEA region to make sure that we are a cohesive unit, working together across departments and making sure that we’re not siloed.
So when we were a smaller company, things were very flat. It was a very flat organization, which was nice. But what we’re starting to realize is you kind of need that hierarchy to be able to grow as a company.
But within that hierarchy, you’re kind of building a net. You need to make sure that you’re not losing the connection between different departments and between different functions. And that’s where my role comes in to kind of make sure that things are maintained and communication is still open.
Why CS and Operations Sit Under the Same Function
Irina (5:03 – 5:36)
Before I ask you what the relationship is and what processes you built between the teams, I want to ask you why CS and operations? Why do you have two different teams that sit under you? And I’m curious more about the thinking process behind this decision and what let you make the separation between the two?
Mark (5:36 – 7:58)
So it’s a great question. The customer success team by us has really been one of the cores of the business. Certainly, the core in the revenue operations of the business and in terms of the functionality.
In most organizations, certainly in SaaS-based companies and startups and things like that, customer success is the heart of the organization. Now you have R&D, you have sales, you have operations, but the nucleus is customer success because customer success is your outward facing ear on the ground talking with your customers, engaging with them, and then it also needs to report that back into the business for product and R&D to understand where the product should be shifting, what we should be focusing on, as well as the sales. So it happens to be in CloudStore, our customer success team is also a very large part of revenue generation.
One of the big philosophies was land and expand. So many of our customers start, they start small, they’re not sure if they want to engage, and we can get into the whole market of virtual labs and why that is because that really took off from COVID times. So many, many customers will be like, they want to like get their feet wet, but then they’re going to grow from that point.
So our customer success team has been a core part of that business to be able to take the customer and grow. So I think that’s really, really what’s been very important. I think the reason operations merges kind of into customer success really well is because operations is like the arm.
If you’re going to say customer success is the body, operations is the arm of that body. When we, you know, in our CRM, customer success is working there every day, but operations is controlling it, making sure that everything’s connected and integrating with our finance system and our billing and into product and things like that. So customer success needs to be able to go ahead and provide that information and provide that clear data to operations.
So it makes sense for them to be tied together really close.
How CS Connects Sales, Legal, Finance, and Product
Irina (8:00 – 8:37)
Speaking about that internal alignment that you need in order to support the systems that you’ve built, how did you reach that alignment between sales, pre-sales, finance, revenue operations, etc? By the way, what’s the difference between finance and revenue operations? Who does what?
I’m curious how the CS, being in the center of everything, interconnects to make sure that you reach this alignment?
Mark (8:37 – 10:57)
Great question. So specifically, finance deal, our finance team deals with all the finances of the business. So you’re talking about budgeting, you’re talking about accounts payable, accounts receivables, things like that.
Revenue operations is specifically focused on essentially maintaining our CRM and maintaining the integrations that we have between our CRM and our deal hub center along and how that passes through to billing. So they’re maintaining and building the kind of functionality and the logic between how it flows from the deal pre-signing of the deal and how that goes ahead and triggers into accounts payable, accounts receivables, and collections, and all sorts of things. So that’s where revenue operations sits.
So they maintain kind of our CRM, make sure everything there is clean. And customer success has to focus in the middle because what customer success is doing is let’s say you’re in the heart of a deal. And this happened to me recently in a deal that I was closing right before the end of the year.
And you’re negotiating a deal, you’re working through it with the customer, and then all of a sudden a legal question pops up. So immediately your head has to shift and you have to go to the legal team and figure out an answer. And then the terms of the deal they want to change.
Well, now the terms of the deal, I have to go to finance and figure out if the terms align. And they have a custom clause that they want to put into the contract as revenue operations. So I have to go to the revenue operations to go ahead and change the terminology and add the custom line item that they want to go ahead and add.
So it’s all of these different little moving parts where revenue operations isn’t going to talk to legal necessarily, and they’re not going to talk to finance about it. Finance isn’t going to talk to sales. It’s going to come through us.
We’re filtering all that out. So we’ve, thank God, been really, really good at doing that. It’s a very, very tough job because you’re wearing multiple hats, but it’s very rewarding.
And when it works well, it’s like a beautiful symphony. So it’s gone really well for us.
Irina (10:58 – 11:16)
What operational system has made the biggest difference in how your team runs today? It might be a system or maybe just a process that it’s over underappreciated, but it has a bigger impact than people realize.
Mark (11:18 – 13:58)
It’s interesting. And I know many, many people are probably struggling with this as we have. I mean, we’re actually going through a fundamental change within our operational systems as it says.
Our CRM used to be our single source of truth. So that’s probably the main one that we’ve worked out. Now we’re actually in the process of purchasing a CRM system, not a CRM system, a CSM system to be able to have more of those insights into the customers and help automate different flows.
So I think it’s more been the process that we’ve put in place. It also starts from the hiring, the people that we’ve hired and the process, the people in the process have made the difference. Now it’s easy to have a system in place, but if you don’t have people that understand how to use the system or they’re not following the specific processes that you’ve built out, that’s where things will kind of fall apart.
So for us, it’s been this process of setting up, how often we should be reaching out to customers. When we reach out to them, what should we be talking about? How are we laser-focused on adoption and usage of our system?
Making sure that we have different touch points. One of our biggest ones, NPS scores. We make a point to when a customer sends an NPS response and they give a feedback, we respond to every single one.
And I can’t tell you how much of a difference that has made to our customers where they send this, they think nobody’s reading this, nobody cares, but sure, I’ll tap a score and send it back. And you probably have seen this as well so many times. I’ve literally received emails back from customers that we’ve responded to saying, wow, I didn’t think anyone read this.
And it makes such a difference. It makes such a difference because they feel heard. And many times that’s all the customer wants.
They want to feel heard. And sometimes you can help them with the issue that they’re having and sometimes you can’t. But just the fact that you’re there, and that’s one of the fundamentals as a CSM, is you want to be there as an ear to your customer, and you want to feel heard, and they need to feel heard.
And just you being there and responding to them, engaging with them, goes a long way in terms of building. So it’s funny. You always love to see positive NPS scores.
My favorite is receiving the negative NPS scores. Because to me, that’s the challenge, when you can take a negative NPS score and turn someone’s negative experience into a positive experience. And that’s what we like to focus on.
What Breaks First When a Hands-On Approach Meets Scale
Irina (13:59 – 14:28)
You know what I’m curious, as teams grow, and you went through this process, things that work with five customers suddenly break when you go to 500 or 1,000. What was one process that, in your case, used to work and it didn’t when you went through the journey of scaling?
Mark (14:29 – 17:26)
This is a great question. And I have a number of examples in my head, because it’s something that we have prided ourselves on for a long time, which is being very hands-on, very customer-centric. But when you do that, it’s not necessarily scalable.
So I have two examples. The first, I can even just stick on the NPS score, for example. The fact that we respond to every single NPS score was a very tedious task and very time-consuming.
So yes, we built templates for that. But we actually now have been in the process of automating it. Because before that, when you have 10 NPS responses a day or something like that, that’s okay.
But when you start having 20, 30, 40, 50, and it’s spread amongst the team, you just can’t actually respond. And then you know that your response is going to lead to responses from those customers, which is going to in turn lead to more and more work. So we’ve started to automate that process.
But what I really wanted to do is not lose the personality of the responses. So we’ve actually been able to build an automation that we’re releasing soon that the responses are going to come from the individual CSMs themselves, and the replies are going to go back to the CSMs themselves. So what we’re doing is we’re taking away a lot of those tedious tasks and automating it, but we’re keeping the personal touch involved in that automation.
So that’s certainly one example. A lot of the individual touch points, like when we build out and say, these type of customers need to be reached out on a bi-weekly cadence, and these need to be reached out monthly, and these need to be reached out every three months, we need to have a quarterly business review. That process also needed to start being automated, because you don’t want your CSMs to be so focused on the operational duties and the minutiae of the day.
You want them to be focused on the customer. So that process started breaking, because as we grew, there just weren’t enough hours in the day to do all the tasks that you needed to do. And even a third one, I would say, is notes.
I mean, we did a lot of note-taking on calls, putting that note-taking into our CRM, which would take a long time to write up all that. You have a call, and let’s say you have back-to-back calls, and all of a sudden you’re getting lost as to which call you were saying what. So automating that process, we’ve had to, and that’s where AI has come in and made a huge play into what we do, because note-takers from years past have been okay, but never necessarily accurate.
But when you start creating the right prompts and being able to extract the right data and key points from a call, that’s something that we’ve been heavily focused on as well.
What to Look at First When Building CS Properly
Irina (17:27 – 17:41)
When you walk into a company that says, ” We need to build customer success properly”, what’s the first thing you actually look at?
What are the ingredients to do that?
Mark (17:43 – 20:50)
First and foremost for me is people. It’s the people you hire, the CSMs you hire, that make all the difference. I’ve been on many different teams and built many different teams. For me, it’s all about hiring the right people who are ambitious, who want to learn, who are humble, who are team players. That’s what I look for. I don’t even necessarily look for whether you’ve hit this target or that target. I look for personality, because at the end of the day, people can learn. You’re looking for personality, a willingness to learn, and people who want to succeed.
So first and foremost, it’s the people you hire. Secondly, it’s the process you build. People are great, but unless you have a process for them to follow, they start doing their own thing and things go sideways. So it’s people and process, and third, I would say, is the systems you have implemented. Because if you have the right people in the right process, the system will function as well. Things might take longer and might break as you scale, but that’s why I would rank it in that order.
I heard this on a call with Steve Bartlett, and it really stuck with me: when you hire the wrong people, and many times nowadays those are the high performers and high achievers who are willing to step on the person next to them to reach their goals, they perform in dollars and cents but they bring the team down.
For us, it’s all about having a cohesive unit working together towards a common goal. High achievers who are not the right culture fit don’t have a place and don’t last long. CloudShare has been around for almost two decades, and I’ve been here for six years, which in a SaaS company is unheard of. People are hopping around everywhere. But I find you can figure out very quickly who is going to last and who won’t. The ones who don’t, within about 12 months they’re out, either pushed out or they leave on their own. And the ones that last, we have people at CloudShare who have been here for over a decade. It’s those people who fit the culture, fit the trajectory of growth, and have the right mindset that really last.
People, Culture Fit, and Why High Achievers Don’t Always Last
Irina (20:51 – 22:07)
I really like what you said. Everybody wants high achievers and overachievers on the team, but it can jeopardize team cohesion. And I think it’s more of a sprint rather than a marathon. It’s all about whether you want short-term success or whether you want to build something that lasts.
It tells a lot when people stay with a company for more than a decade. It means you have a very strong company culture and company values. And one year to see if it’s the right fit, I think that’s a fair thing.
Company culture and company values matter more than anything else, because you can have successful people in the wrong environment, and it’s not only because of them. It’s also the environment they operate in.
Mark (22:08 – 22:16)
How many times have you seen that? How many times have you seen where it’s the high achiever, the one with 100 percent of their targets, they get promoted into a managerial position?
Irina (22:17 – 22:56)
And then they fail, and everybody asks why. Because it’s a different job. Management is a different thing than achieving a target. I know what you mean.
I want to ask you one last question. You put a lot of focus on hiring and people. If you had to start a CS organization from scratch with only three people, what roles would you prioritize first and why?
Mark (22:56 – 25:26)
If I had to start a CS organization from scratch with three people, I’m going to spread the net a little wider here.
First, you need an all-star CSM, because you need someone on the ground managing customers and being the front-line soldier. Second, revenue operations, because it sounds like a given but it’s not. Revenue operations is the back-end support that makes sure all your data is clean and things are running smoothly. And your CSM is not necessarily good at that. I know many CSMs that are phenomenal at what they do and are the worst note-takers, the worst at making sure everything in the system is clean and updated. That’s where revenue operations comes in. Rev ops is so important.
And third, you need a team leader. Without leadership, there’s nowhere to go. Leadership drives the vision and the forward movement of the company. You can easily get bogged down in the day-to-day, and I find that in my own role, where I still manage a book of business, manage a team, and have to think at a strategic level, you need to be able to separate the two and step out.
Sometimes a customer has a problem or a feature request, and the CSM’s job is to drive that back into the business and say, they need this, I need to deliver on this to keep them happy. But then it’s leadership’s job to say, wait, does this feature align with where we are going as a company? Does it help other customers or only this one? It’s very important to have that strategic mindset to ask, how is this going to make an impact on our company globally?
That’s why leadership, CSM, and rev ops gives you the full circle of what you need to get started.
Irina (25:28 – 25:48)
Mark, this was a great conversation. And I enjoyed digging into how CS involves a team scale and how operations start to play a bigger role in making it all work. Thanks again for joining me.
And to everyone listening, thanks for tuning in. Until next time, stay curious, keep learning, and mastering customer success.
Mark (25:49 – 25:51)
Thank you for having me!
