In this episode of Mastering CS: Candid Leader Insights, Irina Cismas sits down with Kristin Maguire, Senior Customer Success Manager at RocketLane, a platform for running customer onboarding and implementation projects. Kristin spent most of her career on the implementation and onboarding side before moving into a strategic CSM role, and that foundation shapes how she thinks about outcomes, adoption, and the role AI should actually play in customer success.
She shares why AI needs to be layered into outcomes and not treated as an auxiliary feature, how she uses RocketLane’s MCP connection with Claude in her day-to-day work, what adoption really means beyond login data, and why the most important lesson she has learned is that personal rapport with a customer never guarantees a renewal.
What You’ll Learn
- What RocketLane does and what the Senior CSM role looks like post-onboarding
- Why AI as an add-on is the wrong mental model and what the right one looks like
- How Kristin handles the build versus buy conversation at renewal
- How RocketLane’s MCP connection with Claude changes how she manages workflows and learns the product
- What AI signals she uses to catch churn risk and upsell opportunities she might otherwise miss
Key Insights & Takeaways
AI needs to be tied to outcomes, not treated as a feature. When teams get broad autonomy with AI tools, everyone runs in a different direction. The job of CS is to help customers use AI in a way that actually drives the value they bought the product for.
The Lego analogy explains build versus buy. Anyone can piece together something that looks like a rocket. But the tool you purchased gives you the pieces and the instructions for the branded version. That’s a fundamentally different result.
AI signals catch what you miss in your sixth back-to-back meeting. Scraping conversations and emails for churn risk phrases or upsell sentiments is exactly the kind of background work that scales a CSM’s attention across 30 plus customers.
Token consumption is not an adoption metric. Someone who uses fewer tokens but gets better results because they know what to ask is more valuable than someone burning through tokens without direction.
Podcast Transcript
Intro
Irina (0:00 – 0:26)
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 Kristin Maguire, Senior Customer Success Manager at RocketLane, a platform for running customer onboarding and implementation projects. Kristin, I’m really happy to have you here.
Thanks for joining!
Kristin (0:27 – 0:29)
Thank you so much for having me! It’s an honor.
What the Role Looks Like After Moving from Implementation to CS
Irina (0:30 – 0:40)
You’ve spent most of your career on the implementation and onboarding side, and now you are a senior CSM at RocketLane. What does your day-to-day actually look like?
Kristin (0:41 – 1:26)
Yeah, it’s a great question. So I’ve spent a lot of time, like you said, on the onboarding implementation side, and so now I’m really focusing on that next step in the customer lifecycle where we’re looking at the values and outcomes that the customer is trying to achieve through the relationship with the tool. So for me, my day-to-day is no longer specific tasks or trainings that would go along with onboarding and implementation.
It’s more strategic, thinking about how the customer fits into specific initiatives or how RocketLane can help the teams with their initiatives and really building a relationship that is spanning the duration of their contract and beyond.
Irina (1:27 – 1:33)
And right now, what’s the one thing you are trying to move the most? What keeps you up at night?
How to Handle the Build Versus Buy Conversation at Renewal
Kristin (1:34 – 3:02)
I think that there’s so much conversation about build versus buy in AI, and I think that every SaaS tool, no matter what you’re working with, has this kind of conversation. So what keeps me up at night is this idea that AI is an add-on to our industry. It’s not.
It is something that needs to be layered in a specific way. For me and for my customers, what I’m trying to get to is that these agentic layers are core functionality, things that will help your team become more efficient, but it’s not a replacement for an onboarding. It’s not a replacement for an implementation or even a customer success manager.
It is truly a tool to help aid that needs a significant investment, but true governance, which is why that conversation keeps coming up. Teams are giving access to tools like Claude. You can build your own processes, but then we’re seeing that everybody runs in a different direction, but you purchased a tool to help you ultimately achieve a goal.
So instead of giving sort of this broad autonomy, maybe let’s try and focus in on what AI would actually help your individual contributors, what would help the actual value and outcomes. So that’s what’s keeping me up at night is the tie between these outcomes and values and AI as opposed to it being seen as this auxiliary feature.
Irina (3:02 – 3:59)
I’m so glad that you brought it up early in the conversation and I want to continue on this topic because I think you are one of the few CSMs that put it out bluntly. I usually ask the question build versus buy in those conversations, but you basically said it first. How do you convince?
Because I assume that this topic makes the renewal conversation harder because the client is under the impression that, okay, I can build that tool where I can replace RocketLane with Claude on top of the things that I have. I no longer need it. How do you not necessarily convince, but how do you prove the value?
What are the arguments that even if you bring a Claude or ChatGPT on top, you still can’t replace what RocketLane can do? What are your arguments in those renewal conversations? Let’s say it.
Kristin (4:00 – 6:27)
Yeah. So we’re not seeing that customers are feeling that they can completely replace necessarily, but we are seeing that customers are deeply embedded in the AI of all of the tools that they use. So one of the things that I’m lucky to be working at RocketLane that they invested heavily in our MCP.
So the connection protocol between RocketLane and a system like Claude are open. It is available for our clients to use. They can pull certain information using that connector.
And so it does allow them to piece together certain things from other tools as well. So they can use our MCP to optimize certain workflows. But I was having this conversation with another CSM the other day, and it was like, I think about it.
My husband loves Legos, right? So I think about it this way. If you’re given a bucket of Legos, and I said, build a rocket, you could build something that kind of looks like a rocket, right?
You could piece together some stuff, depending on your skill level. Let’s say you’re a Lego master, right? You could get a rocket, right?
But not everybody has that skill level. Most people are coming at it like me, who might not have the technical background in Legos to be able to build this structure that looks something like a rocket. But what the tools that you’re purchasing do is they’re giving you the Lego pieces and the instructions for the branded rocket, right?
So what you build using these AI agentic tools that are layered into your systems is a lot better than individual contributors or even folks that are not as developers, engineers. You’re giving them the tools to be able to achieve more, something that actually looks like the rocket. So for that conversation, we’ve invested heavily in that layer.
It’s become core functionality. But when I have the conversations with the clients, it’s more like, I’m starting to see the outcomes that you’re trying to drive. Let me help you to use the AI that’s within the tool, because that’s actually going to push you towards the outcome that you purchase this tool for.
Let me help you build the rocket with the instructions, as opposed to like piecemealing something from just the pieces.
Irina (6:28 – 6:41)
I really like the analogy and the way you explain it. And while you were describing it, I had the Ikea analogy. It’s like building an Ikea furniture, but you don’t receive the manual of instruction.
Kristin (6:41 – 6:51)
If you have the pieces to build that shelf, it might come together, but you might also end up taking a hammer to a screw. And that’s not exactly what you want.
How Kristin Uses AI Day to Day as a CSM
Irina (6:52 – 7:06)
Indeed. Let’s continue on the AI part, because I’m curious, how do you leverage it? And what are the use cases where you use and leverage AI on a day-to-day?
How is the CSM at RocketLane use the AI functionality?
Kristin (7:07 – 9:02)
Yeah, so I would say that there’s a couple pieces of Rocket.Lane AI that I use, and then also Auxiliary AI, right? So we are in the camp of using Cloud. We do use our own NCP.
If I need to update tasks in a project, it’s easy for me to tell Cloud, hey, this is what I’m working on, help me to update this. And it works. And it works in that way.
The action is there. It’s very conversational. And I like that.
The AI that I have started layering in for my own workflow is within Rocket.Lane is more of our signals, being able to get to the point where you’re hearing, you’re scraping conversations and emails for some of these kind of trigger words, right? Or phrases or sentiments of churn risk or of upsell opportunity, because at the end of the day, you’re sitting through the conversation, you’re sitting through the emails, and you might have 30 plus customers that you’re working with. You are not going to process every single signal that you are receiving.
It’s just impossible, right? And so these AI tool recordings, these AI signals can help to identify things that you might not have caught on to when you’re in your sixth back-to-back meeting, which is, I think, something that a lot of customer success managers are dealing with now in our kind of virtual ages. Accessibility is very common.
So being able to get on a call with your customer is great. But what do you do with the information and all of those like kind of soft signals that you’re receiving? So the AI that I use is more to make sure it’s a gut check.
It’s something that’s in the background to help me. And then as I have time, as I sit down and block off my calendar for follow-ups and for note-taking, I can take a look back at that and be like, oh, right, okay. So like that was something that I maybe should consider a little bit deeper.
Who Is Actually Building the AI Tools the Team Uses
Irina (9:03 – 10:20)
Another thing that I’ve heard a lot in the past six months is that CSMs are measured on how many AI tokens are they consuming? Because every company wants to have, yes, because the CEO wants to see the AI adoption. So because there is no metric on how do I know if the CEOs are up to speed with this, with the technological wave, they put a metric.
How many tokens did you spend? And basically in my conversations with the head of CS or senior CSM people, I have the feeling that I’m talking with technical people because everyone is building, is doing, is. I’m curious, what’s the, who is building all the, who is enabling the agents, the skills, AI skills that you guys are using?
Are you building it on your own or you have inside the organization, a dedicated team that roll out those kinds of things? You basically make the request and somebody with a technical background is basically implementing it and is facilitating those, those skills. Do you build it on your own or there’s that?
Kristin (10:20 – 14:07)
Can you get some help? Yeah. So for two, two fold there.
So the native AI within Rocket Lean is built by our engineers. So that, any of the AI that I use for that is built with purpose. So I feel confident in using those AI agents myself because they’re still conversational, but they were built and designed with the tool in mind.
For the auxiliary type of AI that we’re seeing in the CS industry, I think we’re all kind of building, right? We’re all seeing what’s possible. And I would not consider myself to be a builder.
I certainly wouldn’t consider myself to be an engineer. I was a technical account manager at one point, and I think I have enough skills to be a little dangerous, but not enough to maybe build something that I think a lot of people will use. But what we’re seeing is that there’s different skill sets on the CSM team, right?
For me, I am a people person. I love talking to people. That’s why I love this opportunity.
And for me, I can talk to Claude. I can be like, Hey, this is what I’m looking at. This is what I’m thinking.
This is what I’m doing. Right. And when it connects to certain systems, I can get back real time results.
For example, scaling at a new company, I’m only six months into Rocket Lean. So how do you learn a whole product? I’ve been in the PS industry, but like, how do you learn a full new tool?
Being able to ask Claude questions and it searched the help docs in a way that is conversational, launched me way faster than any other company I’ve been onboarded at just based on that tool. But there’s different skill sets within the team where we’re seeing some people who really do have the builder mindset are building tools that other team members can use. We have one guy on our team who is phenomenal at this and has really made it his mission to help us with things like observing the outcomes, right?
Building an outcome library as an app, as opposed to it being a deck, which is something that I wouldn’t have even thought about six months ago. But now I’m able to put some inputs, give it my kind of CSM authority into this tool. And it’s popping out real outcomes that I can start to discuss with my clients, which may not be exactly what they’re looking for, but it’s a start to the conversation, which is what I think all of us as CSMs are trying to do is take the information that we have and start the conversation.
So I think to your point, it may not be every single person, but I think that there are certain people on the team that are doing it in different ways that can help others. And CSM is a team sport, right? We have to work with every single department and we have to work with each other.
So why not share that kind of Commonwealth? The idea that you’re tracking CSMs on AI token usage is interesting because one of the main kind of metrics that a lot of CSMs look at for their own tools that they’re working with their customers is adoption, right? And an adopted customer is not always a happy customer.
So it’s interesting that they would be looking at the adoption of some of the tools that they implemented. Let’s say they heavily invested in a cloud license, seeing how many tokens you use. What if somebody is a lot more efficient at what they’re doing using a little bit less tokens, maybe they have more institutional knowledge.
They’re not asking it a ton of questions like I am as a new person, but they’re getting better results because they know what to ask it. I think that adoption question has always been an interesting component for CS. And I think it should be considered at the leadership level when looking at these AI tools as well.
What Adoption Actually Means and How to Measure It
Irina (14:08 – 14:32)
You hit a sensitive nerve, I would say. Let’s talk about the adoption and how do you measure adoption or what does it mean for you particularly? What are you measuring when you are trying to see if the customers that you are taking care of are basically adopting the tool?
What are you looking at and why?
Kristin (14:33 – 16:44)
I think that there’s, for all tools, you have this idea of if you’re in a seat license situation, you’re seeing are all of your seats utilized. If you’re in an open model where anybody can log in and you’re trying to see unique users month over month, making sure that you’re getting either a steady increase or you’re really staying flat. But adoption comes from the culture within a company.
I sometimes, maybe this is also maybe something not to be said, but I’ve said to customers before, let your team hate this for 24 hours. Let them get out the change management ick that they get from it and then let them just explore it and get into it. For me, it’s more the pilot team, the team that you’re working with.
Are they really enforcing this tool? Is there anything that the team that uses this tool is measured on that can be tracked within that tool? Is there anything that’s tied incentive wise to using this tool?
The teams that end up with the greatest adoption, it’s usually the non-starter where the leadership team at that company or the team that’s managing that relationship is like, everybody has to use this. It’s part of your job. And when you make it optional, even if you’re getting that person to log in, even if they’re consuming a license, they may not be using it in the same way that somebody who has to use it is.
And it’s not to say that it needs to come down and be very strict of you have to use this tool. But I think it’s important to have that conversation with the leadership of the customers that you’re talking to is like, how does this actually fit into your ecosystems? Do team members reach for this?
And what would make them reach for it more? What’s the enablement strategy that you use internally? Because we might train five to 10 people and then they’re dispersing that knowledge.
It’s like, how can we help with that? And it might be getting too in the weeds for a customer success manager to be offering to do more enablement or whatever that structure might look like at your company. But I think that’s the kind of engagement you’re looking for.
It’s not necessarily based on this very high 30,000 foot adoption level.
The Habit That Has Carried Kristin Through Every Role
Irina (16:45 – 16:59)
Cristin, last question. Being in support in implementation and knowing customer success. Is there a habit, a way of thinking or something you learned the hard way early on that still shows up in how you run accounts today?
Kristin (17:01 – 18:36)
I think that no matter what function you’re in post-sales, customers want to be heard. And providing that space is exactly what we’re here for. It is 100% a team effort between all of the post-sales functions, including account management, including sales.
There is nothing greater than keeping a customer happy, keeping them successful. And sometimes that is telling them no, or telling them that they’re not doing something the right way. And that’s a very uncomfortable thing to do.
But for me, it’s having seen it in all different kind of lights is that you want to make a strong impression. You want to follow through on what you’re kind of offering. And you ultimately want to think about their success because their success leads to your success.
And you want to make sure that what you’re presenting to them makes business sense for them. It’s not going to make any difference how much you like a customer. I’ve had many customers that I vibe with incredibly.
And I think that they are just fantastic. And their company just pulls the tool because of X, Y, and Z. And it’s not about having this personal relationship.
It’s truly about making sure that the person and the teams that you service are successful within the organization. So it’s a hard lesson to learn sometimes. You always think, oh, they would never churn.
They’re so wonderful. They’re so sweet. They always take my calls.
If you’re not helping them to be bottom line successful, then you’re not doing your job.
Irina (18:37 – 18:55)
Listen, this was a really interesting conversation. Thank you for taking your morning, early morning time to talk to me today. Thank you so much.
It was a pleasure. To everyone listening, thanks for tuning in. Until next time, stay curious, keep learning, and mastering customer success.
