In this episode of Mastering CS: Candid Leader Insights, Irina Cismas speaks with Gillian Stringer, Senior Client Partner at N.Rich, an account-based marketing (ABM) platform that helps B2B teams engage high-value buyers.
Gillian breaks down the shift from “traditional CS delivery” to owning business outcomes through change management, sharper commercial judgment, and earlier expectation-setting. She explains why “protecting the relationship” becomes harmful when it conflicts with business growth, why churn conversations fail when they start after churn intent is declared, and how strong CS-Sales alignment starts before the deal closes.
What You’ll Learn
- Why change management becomes central as CS roles grow more strategic
- Why selling features rarely drives expansion
- The misconception many CSMs have about being “commercial”
- When protecting the customer relationship can backfire
- Why churn mitigation rarely works once churn is announced
- The foundations of strong renewals: ICP fit, onboarding, and milestone-based success
- How forecasting churn improves control over a book of business
- How CSMs build stronger relationships with Sales teams
- Why agreeableness does not define great Customer Success
Key Insights & Takeaways
Customer Success becomes strategic when it focuses on outcomes: The role evolves from platform enablement to guiding customers through organizational change and business impact.
Expansion works when it starts from customer goals: Feature-driven upselling rarely succeeds. Growth conversations work when tied to business needs.
Churn prevention must start early: Escalations after a customer announces churn rarely change the outcome.
Renewals begin with the right customers: Clear ICP alignment and personalized onboarding significantly improve retention.
Strong CS–Sales collaboration prevents bad-fit deals: When CSMs support sales conversations early, they build trust with both customers and account executives.
Great CSMs are not just agreeable: Success in high-growth environments requires firm conversations, expectation management, and ownership of outcomes.
Podcast transcript
Intro
Irina (0:10 – 0:29)
I’m your host, Irina Cismas, and today I’m joined by Gillian Stringer, Senior Client Partner at N.Rich, an account-based marketing platform helping B2B teams engage high-value buyers. Gillian, I’m really happy to have you here. Thanks for joining!
Gillian (0:30 – 0:36)
Thank you so much, Irina! That was such a brilliant introduction. I’m really excited to be here and get into the conversation today.
From CS execution to strategic partnership
Irina (0:38 – 0:54)
I want to go back to the roots. You started in hands-on CS roles, and now you are a Senior Client Partner. When you look back, what’s changed most in how you show up with customers?
Gillian (0:56 – 2:45)
Yeah, it’s a brilliant question. What has changed most is recognizing the need for change management. In my previous CS roles, I worked in organizations where there wasn’t necessarily a broader theory behind the tool.
Now, in the account-based marketing landscape, I primarily work with marketing teams, but I need to champion the idea that marketing and sales teams can work together and stay aligned. There doesn’t need to be animosity. We need to involve CROs, CMOs, and CEOs, and it’s not enough to simply enable the platform. I can’t just set you up with a login and check in at the first QBR.
I need to truly understand the organization, where they are today, and where they want to go. The success of N.Rich depends on the success of the business. If they don’t hit their revenue goals, it doesn’t matter how many accounts we engage on N.Rich.
That change management element wasn’t part of my day-to-day when I first started my career. I’m glad it wasn’t, because I wouldn’t have known where to start. My role used to be explaining technical concepts clearly and helping customers get up and running on the platform.
Now I am a partner. We work alongside each other, and your KPIs and business goals matter just as much to me as something like the last time you signed in to N.Rich.
Early lessons about expansion and commercial thinking
Irina (2:46 – 3:13)
We’ll talk more about that partner label and what the difference is, but now I want to ask you, in your career, when you were handling this traditional, let’s call it CS part, how do you think about growth or expansion, if at all? Was this part of your mental model back then or not really?
Gillian (3:15 – 4:30)
I’d say it was, but not in a customer-centric way. I wasn’t thinking about expansion or growth from the perspective that creating value leads to revenue. Instead, I thought about expansion in a very basic sense. I had a CRO at the time who told us we needed to be more commercial.
So I tried to figure out what that meant. I started asking myself how to increase contract value, how to get customers to buy a new feature, and how to generate more revenue from existing accounts.
But I wasn’t thinking about needs-based selling or really understanding the goals of the company I was working with and how our product supported those goals. I was going into conversations trying to sell features, which rarely works unless you have a product so strong that the features sell themselves without much context.
So expansion was in my mind, but it came from pressure to be more commercial as a CS function, after operating for a long time without that commercial mindset.
Rethinking the relationship between CS and sales
Irina (4:32 – 4:51)
Speaking about this pressure that you felt back in your day, I think there is still a lot of tension in CS around stepping closer to growth, sales, and revenue conversation. In your experience, what do CS leaders tend to misunderstand about that shift?
Gillian (4:51 – 7:01)
It’s a very interesting question. I think there is definitely this juxtaposition between CS and sales, and between being commercially driven and adding value or supporting your customer.
I don’t know if there’s anything I can say that CS leaders as a whole misunderstand, but I can definitely speak to my own misunderstanding around sales.
My barrier to being more commercial with my customers was simply thinking, “I’m not a salesperson.” That was my stance. But I worked with a really effective CRO who was watching my calls, and he said, “You are a salesperson. You are selling the value of this tool every time you meet with your customers.”
Every time you explain why the tool is necessary and why they should keep using it, you are selling. Any CSM can relate to the fact that it’s not a case where a contract is signed, you go through your QBRs, everything is perfect, and then you renew. There are multiple points in the customer lifecycle where things change. You might lose a champion, things might not go well, something might break, or the tool might not be what the customer expected.
In every one of those conversations, you are selling.
For me, it came down to a misunderstanding of what sales actually is. If you haven’t worked with strong account managers or account executives, you can develop this negative idea about sales. You imagine selling ice to an Eskimo, overpromising, underdelivering, getting the contract, and that’s it.
But actually, it’s about partnership. Especially in SaaS, sales cycles can last three, six, or even nine months. Sales teams spend that time building relationships, understanding customers, and helping them.
So I had some misconceptions about what it meant to be a salesperson, and I felt that being commercial was at odds with what I was already doing. Now I see that it isn’t.
When protecting the relationship becomes a problem
Irina (7:02 – 7:32)
I want to talk about the motivation because it is connected to what you actually said. I think most sales leaders generally want to protect the customer relationship. This is why they don’t want to sell it.
But in some cases, this might actually backfire. Have you seen those types of situations? And when do you think that instinct of protecting the relationship actually backfires and doesn’t help you?
Gillian (7:33 – 10:45)
I think if protecting the relationship is at odds with the growth of the business you work for, that’s a fundamental problem. If the business isn’t growing and you’re dedicating time, effort, and resources to building features and improving the product, but no one is buying it, then you won’t have a relationship to protect.
Protecting the relationship should mean delivering maximum value from the tool. As a CSM, if you’re working with leadership that trusts you, you should be able to say that a client is already maxed out in terms of spend and value. They don’t need anything else, and that should be the end of the conversation. There may be no more growth potential in that account within the current renewal cycle, and that shouldn’t be a problem.
Where I’ve seen protecting the relationship backfire is when it conflicts with protecting the integrity of the business and its ability to generate revenue.
Sometimes it’s also a visibility issue. N.Rich is a very flat organization. I often sit with our CEO and CRO, we look at the numbers, and I understand what it takes to maintain the status quo and what it takes to grow. Earlier in my career as a CSM, I didn’t have that visibility. I didn’t understand that when my CRO asked me to be more commercial, it wasn’t because he was being difficult. The business needs to grow. We invest in the product and we need revenue to support that.
Of course we track important metrics like GRR and ARR. If you don’t understand that CS is part of the revenue function, you may focus on maintaining the relationship just to be nice or friendly, so the customer likes you. But to what end? This is still business. Your customer works for a company that also has revenue and growth goals.
So you have to be clear about the purpose. And if upsell or cross-sell opportunities truly conflict with what the customer needs, then that’s a different issue. That means the business itself is not customer-centric. But if you work in an organization that is trying to be customer-centric, maintaining the relationship and helping the business grow should not be in conflict. Those two things should move in the same direction.
Timing conversations with customers and when it’s too late
Irina (10:46 – 11:29)
I’m very familiar with the account-based part being on the marketing side of things. So I can totally relate to the things that you are saying. And I know that in ABM, timing and relevance matter a lot.
So I want to create a link to the CS part now. What do CS teams usually misjudge about when to lean into a bigger conversation with a customer? When is the right moment in the journey?
Do you have a timing also in the CS or not really?
Gillian (11:32 – 14:59)
Timing is important. When that moment happens, whether in month one, two, or three, really depends on the nature of the tool, the onboarding flow, and the time to value. That can vary.
But I can definitely say when it’s too late. It’s too late when the customer says they want to churn.
I’ve seen many organizations put huge effort into churn mitigation once that happens. A customer says they want to churn, and suddenly the CEO wants to meet them, the CRO wants to meet them, and everyone is asking about their last feature request. Teams start talking to product and trying to figure out what can be done.
I have very rarely seen that work. Maybe once or twice we’ve turned things around. But even then, the question becomes at what cost.
If a customer is about to churn and you pull out all the stops, committing to a highly individualized roadmap for an account that might not even be enterprise, you might retain the logo. But then you have to ask whether you can realistically deliver everything you promised. If you can’t, the same problem will appear again the following year.
So yes, it’s definitely too late once churn risk is already on the table.
From a CSM perspective, I would say lean in as soon as something feels uncomfortable. Having a 12-month or even 24-month contract can become a security blanket. For example, if I join a kickoff call with a new customer and they start talking about lead generation, that immediately raises a flag for me in the context of ABM.
A part of you might think it’s fine and decide to address it later. Maybe on the next call, or after their first campaign is running. But you have to lean in immediately. Set expectations and have the conversation right away.
It’s also important to understand the motivation behind what they are saying. Often the marketing manager talks about leads because their CMO is talking about leads, and the CMO is talking about leads because the CEO is asking about leads. In those cases, it’s not enough to correct the expectation with one person. You often need to involve those other stakeholders.
You also need to document it and make sure the issue is addressed, rather than hoping it disappears. It won’t. It will come back.
And if the customer is paying attention, they might say later, “I told you in the kickoff that I wanted to generate leads. Now we’re six months in and you’re telling me that’s not possible. Why didn’t you tell me earlier?”
For me, it comes down to integrity. If someone says something and I know their expectation is not achievable, I would rather address it immediately during kickoff. Even if that means escalating the conversation or involving sales again.
I’d much rather do that early than reach renewal and realize we were never aligned on the most basic goals. So I can’t tell you exactly when the right moment is, but I can definitely tell you when it’s too late.
Building the foundation for renewals
Irina (15:00 – 15:29)
And I wanted to come back to the renewal. It might be too late in some cases. I’m curious whether you will lay down a solid foundation for the customer to renew, or at least to have a high percentage of renewal rate later on in 12 months or in 24 months.
What does it need to happen in your particular case in order to secure that renewal?
Gillian (15:30 – 19:03)
First of all, it starts with sales. It actually starts with new business. I often see CSMs excluded from the ICP conversation within companies, and it’s very counterintuitive.
Some CSMs couldn’t even tell you what the ICP is for their business, and that’s not their fault. They’re simply not involved in that discussion. But that’s where it should start. You need a company that has a clear, tested ICP.
If you’re working in an organization that keeps changing its ICP, that can be expected in an early-stage startup. But in later stages, it becomes a problem. If the company takes a catch-all approach and closes deals with anyone willing to buy, that will eventually show up in churn rates. CSMs are not magicians. We can’t take a bad-fit customer and transform the situation in 12 months.
There has to be alignment around what a good customer looks like. And when I talk about ICP, I don’t just mean firmographics like company size or location. It also includes the nature of the business, their revenue stage, their growth stage, and other characteristics that define whether they’re a strong fit.
Of course, CS shouldn’t be the team defining the ICP, but they should be part of the conversation. If leadership defines an ICP and your CSM team has five or ten accounts that technically fit it but are terrible customers, something isn’t right. That’s a conversation that needs to happen.
From there, the next step is quality onboarding. With large books of business, CSMs sometimes fall into tunnel vision. Onboarding becomes a checklist. First you do this, then you do that, with little personalization.
But customers are different. I work with organizations that are very tech savvy and have been doing digital marketing for years. They add N.Rich to an existing stack and don’t need help with basic platform setup.
On the other hand, I also work with organizations that have done almost no digital marketing, where N.Rich becomes central to their strategy. They require much more guidance. So onboarding has to adapt to the type of customer you’re working with, because a poor onboarding experience almost guarantees churn. The customer might not tell you immediately, but they may already be planning not to renew.
Then you need incremental goals. With N.Rich, we are ultimately trying to impact revenue, but the typical sales cycle for our customers is around nine to twelve months. That means I need to start discussing renewal around the six-month mark.
If I tell customers that success only means closing a deal influenced by N.Rich, I’m setting the wrong expectation, because that probably won’t happen within the first six months. Instead, we define what success looks like at three months, six months, and nine months.
And if those milestones need to change, that conversation has to be led proactively. You can never guarantee a renewal, but having that structure puts you in a much stronger position.
Learning to own outcomes and forecast churn
Irina (19:04 – 19:15)
I’m curious, what helped you get comfortable owning outcomes and not just delivery without feeling like you are compromising the relationship with your customers?
Gillian (19:18 – 21:05)
Bullying. No, I’m joking, not bullying, but pressure. I started as a Customer Success Associate for quite a long time, then moved into a CSM role, and later became a Senior CSM.
The transition from CSM to Senior CSM was quite steep. When you start working more closely with sales leadership, the expectations are higher. You can’t say, “I don’t know why they’re churning. I tried my best.” That doesn’t really work.
So honestly, the pressure pushed me to realize that if I wanted to progress in my career, I needed to own these outcomes. I needed to be bold and have the uncomfortable conversations.
Churn itself is not the problem. Everywhere I’ve worked, churn is acceptable if you can forecast it. If you can’t forecast churn, it means you’re not in control of the account. You don’t really know what’s happening.
If a customer tells you a month before renewal that they won’t continue, the obvious question is what was happening before that. How did you not know? Of course, there can always be unexpected situations.
Taking ownership was something I was initially pushed into. Over time, I embraced it and started to appreciate it. Any CSM knows how unpleasant it feels to receive an email from a client saying they won’t be continuing, especially when you didn’t see it coming.
If you can control the narrative more and look at your book of business with clarity, you feel much more confident. You can say, these are my renewals this quarter, these accounts are not renewing, and these ones are.
That puts you on much stronger footing, and you avoid being in constant reaction mode. After a while, that situation becomes exhausting. So honestly, that’s what helped me shift my mindset.
How CS teams build strong relationships with Sales
Irina (21:06 – 22:24)
How do you build a relationship with the sales team? And how do you make sure that they have your back? Because you need them.
If you ask me, I’m not a CSM, but as a marketer, I know that if at least in a B2B organization, I’m not talking about B2C, I’m not talking about PLG, but in B2B sales-led organization, usually marketing is supporting sales.
So if marketing as a team wants to be successful, they need to join forces with sales and they basically need to work in a hybrid environment. And I see it similar to CS. You can’t have a successful CS organization if sales and CS doesn’t work in sync.
Yeah. And in many organizations, I see a conflict. As you also mentioned at the beginning.
So how do you win them? How do you attract them? How do you force them to be successful?
What do you do in your case?
Gillian (22:25 – 26:36)
I’ll be honest. Salespeople are a dream to work with when they are hitting their targets. When they’re under pressure and missing targets, it’s much harder. I haven’t had much success breaking through in those situations. So I’m really talking about strong reps here, the brilliant AEs who are closing millions per quarter.
With those reps, working with sales becomes a great lesson in what I mentioned earlier about adding value continuously. You need to find ways to help them. It really is a scratch my back, I scratch yours situation.
For example, I join calls with sales reps before the deal is closed. I’ve worked in organizations where CS leadership tried to protect CS by saying a CSM cannot join a call until the deal is signed. I actually think that’s counterproductive.
I’ve helped sales teams close deals by joining prospect calls, giving insights, and building confidence. Prospects often worry about onboarding or about the level of support they’ll receive, especially in the ABM space where licenses can be very expensive. Showing up on those calls as a real person who will support them makes a big difference.
Sometimes I even say that I may not be their CSM, but this is how our process works and how we support customers. Once you’ve done that a few times, you build rapport with the sales rep. At that point, why would that rep knowingly close a bad deal and hand it to you? There’s a level of mutual understanding.
But it’s not only about interpersonal relationships. It’s also about the type of organization you work in. I’ve seen sales reps let go because the deals they close repeatedly churn. Those are conversations companies have to take seriously.
If a CSM sees a pattern where most churn in their book of business comes from deals closed by the same rep, that needs to be discussed. It doesn’t mean going straight to leadership and complaining, but raising the pattern in a constructive way.
If it’s happening repeatedly, five or more times, you can have a conversation with the rep directly. For example, reach out and say you’ve noticed a pattern in some of the information customers received before signing and you want to make sure everyone is aligned going forward.
People who care about doing well usually appreciate that kind of conversation. Some people say sales reps don’t care if their deals churn, but I don’t think that’s true. Over time it reflects on them as well. One or two cases happen, but if it becomes a pattern, it doesn’t look good for anyone.
The myth of the “agreeable” CSM
Irina (26:38 – 26:50)
Last question. You’ve worked across industries, regions, and you had different roles. What’s one assumption about great CS that you no longer believe in?
Gillian (26:53 – 28:06)
One assumption about great CS that I no longer believe in… let me think.
I think it also connects to the fact that CS is often dominated by women. There’s this assumption, even if people don’t say it directly, that a CSM should be a bit of a people pleaser. That you should be very agreeable.
But that’s not right. If you are just an agreeable person who is nice to work with, that may work at the beginning. But if you move into an organization that is trying to grow quickly, and you’re working with enterprise accounts across regions with significant contract value, being agreeable will not lead to success.
In fact, it will probably work against you. You have to get comfortable being firm, being honest, and leading difficult conversations. That’s an essential part of the role.
Irina (28:09 – 28:28)
Gillian, this was such a grounded and honest conversation. And thank you so much for sharing your story and the insights. And to everyone listening, thanks for tuning in.
Until next time, stay curious, keep learning, and mastering customer success.
