In this episode of Mastering CS: Candid Leader Insights, Irina Cismas sits down with Dylan Berno, Head of Customer Success at Coast, a fintech company helping businesses control and track fleet spending. Dylan came from growth, go-to-market, and lifecycle revenue before moving into CS, and that background shapes everything about how he thinks about building a modern customer success function.
He shares how Coast’s CS team is structured around lifecycle stages rather than just account size, how they’ve built a hierarchical agentic system on top of Claude to drive context-aware customer interactions, why data is the foundational requirement for any signal-driven CS motion, and what skills you actually need on a CS team that operates this way.
What You’ll Learn
- Why Dylan moved from growth and go-to-market into customer success
- How Coast structures its CS team by segment and lifecycle stage
- What a signal-driven, telemetry-based CS motion actually looks like in practice
- How Coast uses Salesforce, Braze, Redshift, Grain, and Claude to run its CS function
- Why data accessibility is the single biggest blocker for most CS teams trying to scale
- What the CS team actually does when automation is handling the operational layer
- What skills you need on a CS team that is building toward an AI-driven model
- Why understanding customer outcomes in the first sales conversation changes everything
Key Insights & Takeaways
Start with the customer, not the org chart. Before building structure, tech stack, or playbooks, understand the specific customer the business is trying to serve. Build around the customer, not around a gap.
CS owns every dollar in the business on January 1st. Every retained customer compounds efficiency. Every churned customer resets it. That framing puts CS at the center of profitable growth.
Waiting for customers to ask for help is the wrong model. A proactive, signal-driven outreach motion where the data tells you what to do and when is how modern CS scales without doubling headcount.
Data accessibility is the foundational requirement. You can’t build an intelligent CS motion if your team has to go to business analytics for every SQL query. The data layer has to be easy to access and act on.
Automation frees the team to have better conversations. The goal of the system is not to replace human interaction but to make every human interaction more prepared, more context-aware, and more valuable.
Outcome discovery belongs in the first sales conversation. Getting to onboarding and then asking what success looks like is too late. Those conversations need to happen upstream so CS has the threads to pull on when it matters.
You need three types of people on a modern CS team. Someone who can drive activation and create urgency, someone who is data fluent and can articulate ROI-backed stories, and someone who can build the systems and automate the lifecycle motion.
Podcast Transcript
Intro
Irina (0:09 – 0:26)
I’m your host, Irina Cismas, and today I’m joined by Dylan Berno, Head of Customer Success at Coast, a fintech company helping businesses control and track fleet spending. Dylan, I’m really happy to have you here. Thanks for joining!
Dylan (0:27 – 0:29)
Excellent. I appreciate it, Irina. It’s a pleasure to be here.
From Growth and Go-to-Market to Customer Success: Why CS?
Irina (0:30 – 0:42)
You didn’t start your career in customer success. You came from growth, go-to-market, and lifecycle revenue. Why CS?
What triggered the switch?
Dylan (0:44 – 1:39)
Yeah, I always stayed pretty close to customers. That was something that was really important to me in my career. But I’d say really two things crystallized for me.
First, I realized that on January 1st of every year, customer success was responsible for every dollar already in the business and every dollar that was still available to earn. So I’ve always seen that as the core of profitable growth. Every retained customer compounds your efficiency.
Every turned customer resets it. The second piece would really be, it was more of an observation of how CS used to operate. I think it’s evolved since then.
But from outside, like sales, marketing, I kept seeing CS programs that were busy, but not necessarily outcome-driven. Nobody had defined what success looked like for the customer or the business, and I wanted to run it differently. I’d actually be curious to hear from you.
As you’ve done this, what made you want to start hosting this show? What were you not hearing enough of?
Irina (1:40 – 4:06)
What I realized is that customer success has a different definition depending on the company, the industry, the moment, and the company’s journey. You were mentioning that you realized CS is responsible for the revenue. I was in a similar position, coming from the marketing side and needing to influence revenue. In order to do that, I needed to control the customer journey end-to-end, from a marketing position. Only after two or three years did I realize I wasn’t doing marketing anymore. I wasn’t doing lifecycle marketing or product marketing. I think I was doing customer success, but I didn’t know at that point that it was called customer success.
I think there are different definitions for the same thing. The reason I’m running this podcast is because I want to expose as many customer success models, structures, and ways of organizing as possible, so that others who are either at the beginning of the journey or in the middle of it can get inspiration. The objective is to give others concrete things from real experience. I don’t want to talk from theory. I want to talk from practice. A lot of the resources available online don’t match the reality from the field, and that’s what I want to talk about today.
Since you asked me why I do this, I want to start with your reality. I know that you are leading customer success at Coast. Can you walk us through how the team is set up today, what roles are on the team, and what they own? But before we get into the team, maybe tell us a bit about the organization you operate in, so that we can anchor everything and give our audience some context.
How the CS Team Is Structured at Coast
Dylan (4:07 – 6:50)
Definitely. A little bit about Coast in general is we make fleet and fuel payments easy. We give fleet operators, finance leaders at fleet businesses one place to control, track, and reconcile all of their spend, whether it’s fuel, maintenance, or everything else your team is buying.
Their data is organized by the time finance arrives. With that, we really allow fleet ops and finance teams to focus on exceptions rather than what’s in policy. I think that’s a really important part of how we’ve structured the team today.
Because when we think about this, when I go back to what is CS, how does this look properly, the first thing I really try to understand is the ICP. I want to understand the specific customer the business is trying to serve before anything else, before the org chart, before the tech stack, any playbooks. CS, in my belief, is really at its best as a function that knows its customer better than any other part of the company, or maybe equally as well as product marketing.
But if you start with structure instead of the customer, I really think that you’re going to build around a gap. So with that, the way we’ve really set it up today is that our team owns wholesale, getting customers live, driving product depth, surfacing expansion opportunities. We’ve intentionally kept the model quite lean relative to industry benchmarks.
I think each CSM carries a larger book than you typically see, which means the system’s doing a lot of work. It really isn’t just a relationship layer. And then we’ve extended ownership there into what we’d call growth engineering today, I think, where we’re bridging product data and AI to accelerate both acquisition and retention.
So we are the private expansion motion, we’re the private activation motion. That’s a key of the structure of where we are today. When we get into the team, it really shifts by segment.
The priority sequence is like customers get activated, genuinely start using our product. Then they deepen their usage across features that drive like real ROI for their business. And then we expand onboarding’s foundational, like a customer who doesn’t fully activate, they rarely recover.
So we invest heavily there, especially in the early milestones. And we try to really continue raising our bar for what great velocity looks like. And then in the long tail, like we’ve really moved towards telemetry driven outbound motion.
So our team isn’t waiting. Our perception is you’re doing it wrong if you’re waiting for customers to ask for help. We live in the future now.
We have a lot of fancy tools that can do a lot of cool things. We really say we reach out because the data shows what they’re doing or not doing. And it’s something that matters.
So customers like you who do X and see Y result, it’s a much more compelling frame than a generic check-in.
Segmentation and Lifecycle Stages
Irina (6:52 – 7:23)
Okay. So you have a lot of systems and you have a lot of automation. We’ll talk about that because I’m curious, how do they integrate?
And what’s the AI layer that you are bringing? If the AI is the glue that connects all the things. But before we go into the systems, let me understand.
So the teams are split by, you said by segments and the segments are driven by the customer ARR? Or how did you do the segmentation?
Dylan (7:24 – 7:45)
Yeah. So yeah, it’s based on the size of the fleet that we’re working with. And then, but we also really look at it, not just by when we segment our customer base, we don’t just do it by their size.
We also do it by the life cycle stage that they’re in. And this allows us to have a really informed position when we arrive to have a positive interaction with them.
Irina (7:47 – 7:53)
And may I ask the milestones of the life cycle that you have? How did you divide the life cycle, the stages?
Dylan (7:54 – 8:35)
Definitely. So our stages are set up. Like when you come in through sales, we look at activation and really look at that as a funnel.
Very similar to what an acquisition funnel looks like for a marketing team is what is the utilization by your team? And we want to get you to full utilization as quickly as possible. That’s really what our team is motivated to do.
We have an excellent product. So our retention is like truly best in class. We have great processes and systems to triage and intervene at the right moments to support that.
But we generally have a great product where we’re solving like a true problem out there. So it gives us like a really great opportunity to be more proactive and drive, maintain that level.
Irina (8:36 – 8:43)
Is it more from a go-to-market perspective? Is it a more hybrid motion or product-led in combination with sales-led?
Dylan (8:45 – 9:52)
Yeah, we’re very sales-led, but that’s something we’re working on. And our goal is to make it more of a product-led motion in time and have something that’s like really easy for our customers to use. We have a really flexible product, which like puts us in a position to solve for a vast variety of trades businesses.
But at the same time, that adds some complexity, right? So our team helps people onboard at all times. Our goal is to create the type of environment like that within Coast where our platform makes it really easy to self-serve.
And what’s really cool is living in like the AI world is, you know, we have a great growth team at Coast as well. So like we’ve collaborated with them on creating like using like a lovable cloud code into Vercel. We’re like, we’ve created what our product looks like so we can run experiments of what self-onboarding looks like, what a driver onboarding looks like.
So they know how to use Coast easily. And this has made a meaningful difference in like the value they feel early and like the objections we might face early because we’re different than the historical providers. They’re like that the intention of that is to inform.
These are informed experiments so we can go build this in the product this year.
The Systems and Technology Stack Behind the CS Function
Irina (9:53 – 10:23)
Okay. I think I can no longer postpone the question. Deep dive please into the systems that you are using and into the technology that you have in place to basically run this, run the CS function.
And not only because based on what you’ve told me until now, it’s more than CS, I would say, or more than a standard CS definition. How do all the pieces connect in terms of systems and tools that you guys use?
Dylan (10:24 – 12:32)
We have a really open-minded IT team that sets clear guardrails but lets us experiment in the right environments. And we also have a great growth team, so collaborating with them has really allowed us to start looking at what a modern CS program looks like.
With that, we use Salesforce as our CRM. We use Braze for content, onboarding campaigns, and expansion campaigns. Redshift is the data backbone where we build all of our behavioral risk scoring, spend signals, and usage telemetry. Grain is for call intelligence, so it surfaces what’s actually being said in customer conversations. We use Claude and Attention to enrich our records and systems and help summarize and route insights from those calls into the right workflows.
On top of that, we’ve built a hierarchical agentic system on Claude. We’ve recently transitioned a lot into a Notion knowledge base that houses our CS motion, our playbooks, our product context, and ICP documentation. We’ve then set up a plugin layer that connects that foundation to a network of specialized skills that each own a specific workflow.
It operates across two modes. We have recurring schedules that handle the work that should happen whether anyone asks for it or not: coaching reports, daily digests, call classifications, pipeline summaries. And then we have on-demand skills that handle everything that requires being context-aware for a specific customer need: follow-up emails, ROI analysis, onboarding recaps, lifecycle touchpoints. Both modes draw from the same context stack, what our growth team calls the Coast intelligence layer, and it allows us to be really context-aware in every moment and have things drafted in your Gmail already for you.
Irina (12:33 – 12:46)
Who helped you orchestrate all those? Was it more on the dev team, on the growth team? You keep mentioning growth.
Growth is basically the sales team or is growth where there are two different, different teams. Yeah.
Dylan (12:46 – 13:35)
Our growth team sits in our marketing department. It’s a small but mighty team, five or six people, but we’ve oriented them in a way where they have really specific focuses on customer problems. It’s really collaborative.
I’m a nerd about this stuff. I love building it out. I’m a very ops-minded person, but these types of projects and infrastructure really take a village. It takes people building out the data so it’s easy to call upon in business analytics, and the engineering layer underneath that. It takes people who are really good at building quick experiments, setting them up with code on Vercel, and people who just have creative ideas that we can run and test quickly.
What the CS Team Actually Does When Automation Handles the Rest
Irina (13:36 – 13:53)
It seems like there’s a lot of automation and everything is scheduled. I envision an army of agents working for you guys, and that’s awesome. So I have to ask, what does the CS team actually do?
Dylan (13:53 – 14:01)
Yeah. I’d also say there’s not like an army of agents, right? These are things we’re building towards, of course, but yeah, like our CS team.
Irina (14:02 – 14:04)
The future is going to be an army of agents.
Dylan (14:04 – 15:55)
Our goal has been to shift from high-touch coverage to signal-driven coverage. That way we can scale our team and ask the right questions: what is a modern CS program? What is revenue per headcount? What should our NDR be? What is customer value and outcomes? That’s truly the foundation of all of this. But because we have signals, we can be really intentional.
Our team spends a lot of time getting customers activated. It’s easy to experience friction, and business spend or fuel spend isn’t necessarily in the top three things on a leader’s mind at any given moment. So we need to create value for them and create urgency. We invest a lot of our time into activation and driving progress across a broad range of customers with unique and different use cases.
Our platform continues to add new products, which is really exciting. But the system is what’s allowing us to scale without doubling headcount every two months as our business grows quickly.
To circle back to your question, what our team is doing is activation and intervening at the right moment. We’re getting to a stage of being more than proactive when there’s risk or when people are getting off track. With these tools, we’re genuinely getting close to being predictive, saying, you’re probably going to get off track in a week, right now is the right time to intervene. And what is the right message, and how do we articulate the problems they might be facing so we can get ahead of them.
Signal-Driven Coverage: How Proactive Outreach Actually Works
Irina (15:56 – 16:34)
So this is happening in a meeting? Once you have all those signals, the CS team jumps into a meeting and tries to walk the customer through what’s happening or anticipate where things are heading. Once you have all the signals and the issues connected, is it something that triggers automatically and the CS team is there only to make sure what you’ve orchestrated is working as intended? Or are they also actively interacting with customers? That’s the part I’m missing.
Dylan (16:34 – 17:45)
Oh yeah, sure. So yeah, no, we’re picking up the phone and calling them. Our goal is not to send an email.
Our goal is to have a one-to-one human conversation with them and, but be prepared with like reasons why they should move forward. What is working in the product for them? What is like, we, when our first call every time and our sales team is like continuing to do a better and better job at understanding what the required outcomes are, like when they enter onboarding for the first time.
This has been, it’s something we, I think every business needs to get upstream on where it oftentimes, like you get to onboarding and then the CSM says, all right, what are the outcomes you need to see to make this work? We need to have those, a business should have those conversations like in the first conversation, because it informs everything. And it really gives you all of the opportunities or fruit, if you will, that you need to benefit from and really drive home from them and position.
So that’s it. We understand their outcomes, what value looks like immediately. So that way, when we need to intervene, we know like the strings or the threads to pull on and show up prepared with data to back it up so that it’s like, it is a no brainer for them to move forward.
What It Takes to Build This Kind of System
Irina (17:47 – 18:16)
If I wouldn’t have asked, if I would ask you, what does it take to build the system that you have now in place at Coast? What would you tell me? What does it take in terms of, I don’t know, resources, time, budget, alignment, you name it.
What did it mean for you guys to end up today where you are in this moment? And I understand that things are just started, I would say, and you have big plans moving forward.
Dylan (18:17 – 20:05)
Yeah, we definitely have big plans. There’s a huge problem out there that we have a great solution for. Look, we have a really sharp team.
Everybody that sits on our go-to-market leadership team is excellent. They all have really great perspective and they all want to, they’re all like really curious about the change, how the world’s kind of changing. So like with that, we had a lot of support across the team and my boss like has great intuition around this stuff.
He really has been supportive of it. That’s our CRO. And like I said, on our marketing and growth counterparts and our sales team, everybody’s like really trying to solve this.
We know we have a vision. We know what we need to do. So to like re-architect this, I would say you need events on all of your like data.
You need excellent data of what’s happening in your product at every moment. And it needs to be easily accessible for the CS team. It can’t be like, Hey, we need to go to business analytics and get this SQL query.
We need to have a query builder with AI so they can just go get it. We’re getting closer to the future where now we can just have a conversational layer and say, Hey, Arena is not fine. Like, I have a call with Arena today, this customer, where are some nuggets for them?
Like as simple as that, like what should I be communicating? And it’s really context-aware and provides this stuff. So like the data layer is like a foundational requirement.
You can’t do this without that because you’re never going to be able to call and have the intelligence running. From there, I don’t think it’s that difficult with a lot of the tools. I really think the biggest thing is like getting that data in an accessible way for your teams.
And I think that’s like the biggest thing in front of most companies when I talk to other CS leaders. So like, I’m incredibly grateful for how our team has been proactive setting up this infrastructure. So it’s easy for our team to access.
The Skills and People You Need on a Modern CS Team
Irina (20:06 – 20:33)
So we need data and data at a certain quality. You need the infrastructure. You need the support of everyone.
What about, do you also need some particular skills or who do you need in your team to basically help you or partner up with in the CS team? I understand you need the peer level from the other departments, but in the CS, who do you need to basically build this?
Dylan (20:34 – 21:59)
Yeah, you need great people speaking with your customers. They need to be like genuinely curious about how they can help these customers. That’s like a requirement, right?
The people are, we can talk about systems all day, but like the people are the most important part of all of this. So like you need someone who can get customers to value fast, that has a muscle for activation and creating urgency. You need at least one or two, even in a smaller team, like data fluent CSMs that can read signals, that can manage relationships and articulate clear stories.
That’s major, especially for dealing with your larger accounts or like where there’s like really ripe expansion opportunities as you improve your product. The data fluency and like articulating what that story is, especially backed in ROI and value is a requirement. And then you need somebody who’s a builder.
Like you need people that can build that system, understand the customer journey, establish the right segments, automate life cycle and expansion marketing with clear messaging. And then like now in the future, you need people that can like help set up agents and assistants to intervene at the right moments and serve your team with the context and personalized touches. So they don’t need to go hunt for it.
Cause that stuff takes a long time. I used to spend a lot of my time working on large accounts, like really understanding, like going through all of our communications and like looking for things and like finding patterns. We can automate that stuff today, which is amazing.
Irina (22:00 – 22:51)
I want to end our conversation here because I want to end it in a super positive note because I’m super, I don’t want to ask you. I thought of asking you about the challenges, but I don’t want to wrap it up in a negative thing. I want to leave this on the positive side of things.
I’m sure that it wasn’t necessarily a lean road and you had your fair part of challenges along the way, but maybe we’ll talk about this in another episode. Now I want to thank you for this conversation and it was great seeing how you, what’s your vision about modern CS and what you guys are, what you guys are doing and what you’ve built it and you’ve implemented in order to scale the CS team.
Thank you very much.
Dylan (22:51 – 22:53)
Excellent. Yeah. I appreciate you having me.
Irina (22:53 – 23:04)
To everyone listening, thanks for tuning in until next time. Stay curious, keep learning, and mastering customer success.
