AI for CS Leaders Spotlight: Dee Kachra on Strategy Over Tool

Hey everyone, Angeline here. This episode is part of our AI for CS Leaders Spotlight, where we share real stories from the participants of my AI for CS Leaders Executive Bootcamp. Today, I’m excited to welcome Dee Catra, Season Customer Success Leader. I invited her to the podcast because I know how powerful it is to hear directly from someone who’s been inside the experience. And I’ve had the chance to see Dee lean into the program with a lot of curiosity, thoughtfulness, and intention. And in this conversation, we’re going to talk about her experience inside the bootcamp, what stood out to her the most, and how she’s been thinking about AI in the context of customer success leadership. Dee, welcome and thanks for joining us today. Thank you so much, Angeline. I appreciate the time. Before we dive into the questions, can you give us a quick intro? Tell us a little bit about yourself and your background.

Thank you, Angeline. So I’m a CS Leader with a diverse background starting from procurement, consulting, speech therapy, and then ended up in customer success. And every role was about people, problems, and the outcomes. So in the CS role that I had, I was focused on retention and growth, and I’ve always been drawn very closely to how it connects to revenue. Right now, I’m actually on an intentional sabbatical. I’m upskilling at the intersection of AI and customer success, not just learning about the tools, but also learning about how AI changes the operating model. The decision reflects how I think I had of the change and not just react to it, but how models are going to be changing the CS world. I love that. What I like about this cohort was that there were a few members who were actually in between roles who took this program because they really want to learn and upskill themselves on AI and customer success.

And it’s not like they’re solving a direct problem within the organization or their task to do something. They have something that they need to solve that requires AI. And I think that’s what I like about how intentional you are when you join the program. So what made you join the AI for CS Leaders Executive Bootcamp in the first place? So I’m shifting from operational thinking to a strategic thinking. And what drove me to this program is how we can look at AI and how we’re going to look at strategic, the full system, meaning strategy, data readiness, operating models, governance, not just the tools. You can learn the tool at any time, but you really need to be very strategic in an executive framing and how to move from ad hoc experimenting to something that’s predictable and embedded into your system overall. I like that you said that because the core spirit of the program was it was intentionally not supposed to be technical.

I didn’t want to dive too much into the tool sets because that’s really the latter part of the whole implementation of AI, right? There’s a lot of work that needs to happen, and especially in the context of customer success. Now, let’s dive into your experience in the program itself. How did the format of the program work for you? As you remember, we do release the lessons every Monday, and then we dive into a group call on Thursdays. How did that work out for you? So the modules themselves gave me the framework at the beginning. So we understand the framework, figure out how it all works together in a use case scenario. In my case, it was a use case scenario. The homework honed in to how to apply the framework into the CS workflows. It wasn’t just hypothetical. And then when we got together into the practical calls, you actually saw the framework in a stress tested environment in different organizations.

So myself, other members of the cohort as well had a lot of input in how that worked in their application. So not only you get the framework yourself, but you also get to understand it from different perspective, your industry versus their industry as well. Yeah, that’s what I wanted to do in the group cohort, actually, because each member of the cohort bring a different lens to the program, right? There are people in the program that are actually in the sick of figuring out how to implement AI in their organization. And there’s a lot of opportunities really in the program to learn from each other, especially as you build all of this. Now, what stood out for you across the program and why it could be, you know, a specific module or lesson or an exercise or one aha moment? So what stood out to me was really the framework and the roadmap of where you start to where you adopt and make it scalable.

Currently, at least my experience has been people again are doing things in silos or at the beginning or in the middle stage or have scalability and have already implemented it, but maybe not all the way to their whole organization. So the structure itself and the framework and the roadmap, the governance around how to implement AI in an organization is what stood out to me the most. And where you begin and where you want to end up, you have a focus, you have a thought where you want to end up and you start at the very beginning and you create the whole workflow and the roadmap on where you end up. I’m curious, actually, before the program, how are you thinking about AI in customer success? So before the program, I was thinking about how do I draft my emails, summarize my calls, set up prep time, and really, I just lack the strategic framework. Like, what can I take it beyond that? So there was no shared information.

The output was just based on what I put in input. So I really wasn’t thinking about retention, expansion, CX of scale. It was just input, output, ready to go, next customer. Pretty much that’s what I was thinking about AI. Yeah, which I think makes sense because what I realize or what I observe is that adoption of AI in organizations really often starts with solving a productivity problem and is exactly the use case that you mentioned, right? You’re like, help me write this email and write it faster than you, so you don’t spend minutes or a lot of time just drafting an email. And I feel like that’s why the default mindset when thinking about, okay, how can I apply AI tends to be at that tactical, executional level. But my hope in the program was to give you that leadership lens, right? Because you kind of already alluded to it. It’s beyond your current team, which is how it is today. It’s siloed.

So what shifted actually for you after going through the program? So what shifted for me was the redesign. You can again have the tools, but you need to have how the workflow moves together from the whole customer journey, how to become more efficient, but really how to be strategic about it. You can be efficient all you want. The tools will do the work. There’s pattern there. There is a mentality of the model. It will do the prompting for you. But designing the system itself and removing the operational friction so the CS teams can spend more time being strategic and having a strategic conversation with the customers. That’s the important part. So to me, what shifted was the strategic thinking from a leadership standpoint and how you redesign the workflow, the roadmap, and how you put the guardrails around it and not be in a silo situation for each customer success that you have in the organization.

What’s good about that thinking is that you’re going beyond the day-to-day executional work, which as the example use case that you mentioned earlier, there’s more that you can accomplish with AI. But there are prerequisites to making sure that it’s successful. I actually like the sharing that we usually have during the leadership application calls because there was a lot of inputs around. It’s more than efficiency. I like how you mentioned retention earlier as well or going beyond siloed AI adoption. So after all, the program has ended back in February. What are you excited to apply next? So as a strategic CS leader, what this means to me is that completing the full AI maturity assessment, mapping out where the highest leverage opportunities are and connecting them to real business outcomes. So redesigning the actual workflow from end to end, not just identifying what needs to change, but owning the whole plan and fixing it.

What that means in terms of leadership is that you care about retention, cost to serve, time to value, value realization to the customer, and where AI can be applied in a strategic manner, not in a silo, not just a tool, but going from an operating level to a strategic framework with all the guardrails that are necessary for a company to take this one step further from where they are at the current time. You’re not the first member of the cohort that actually said that, and I like that you are zooming out because obviously this was meant for customer success leaders at AI Executive Boot Camp was made in the context of customer success, but a lot of the principles that we discussed there really could apply across the whole customer lifecycle journey, right? Beyond customer success from pre-sales and then all the way to the end. And I’m glad that that’s resonating because it allows you to think beyond what AI can do for your organization because I do believe as well.

And I think this is one of the things that you said in the program that the next stage of AI adoption is just looking at how all the AI systems and agentic AI systems that you’re going to create in the course of this, you know, I think boom of AI adoption and customer success connects together. I’m curious, is there one skill that you want to keep building over the next 30 to 60 days? I think one skill to me would be thinking strategically overall. You are building the whole system of the CS team. So it’s not just you. It is you and how it impacts or how you can add to your peers and overall the whole organization as well is what is the important part. So strategic thinking and how AI could really benefit everybody. Especially because you always say that customer success is not the job of one department, right? If we zoom out and think about customer success, generally the philosophy behind this is mental and compass the whole organization.

And when we’re thinking about technology that we apply, which AI is one of them, you need to think about the whole structure as well and not just think about it in a siloed environment. Now Dee, coming from the program, I’d like to hear from you. Who do you feel like this program is a good fit for and why? So I think the program is good fit for CS leaders and the operators who want to have the strategic framework, not just utilize the tools. So the leaders that want to strategically think about implementing AI in the whole workflow, in the team, in the organization, but it is also valuable for all the CS members to understand where the leaders are thinking and where the whole team is going moving forward with the AI in their framework and workflow as well. I love that you’re also thinking about the individual contributors. I’ve designed this program for CS leaders because there’s a lot of strategy that comes into it, but there are benefits to the CSM sense themselves understanding how do you implement technology?

Generally speaking, if I think about it in the lens of the course, you can apply it as well. And how do you implement any technology to superimpose it on customer success? Okay, finally, what would you tell somebody who is on defense about joining the program? Maybe thinking about it, maybe have seen the program and what’s it about? What would you say to them to tell them, okay, just join them? Well, success doesn’t come with just using the tools. You really, really have to have a framework and you just don’t chase experiments, not work in silos. Really, you have to have a strategic framework from the very beginning. I’m just doing emails and I’m sending them out to my customers to how I’m going to adopt all AI from pre-sales all the way to the end of the customer lifecycle. But it is really important to have the framework, the governance, the leverages, the objectives, the maturity, where do you start to where you end up, the operating model.

So it’s the full system really. So if you’re in the thinking process of where do I begin and where do I want to go? I think this is a great program for somebody that has that thought to say, here’s where I start and here’s where I’m going to be scalable and adaptable on the whole program for myself. I’m going to see a team and what is important to me as far as revenue outcome, how I’m going to put this all together, but yet have revenue generation, upsells, cross-sells and also upscale my team in order to have the whole framework within the organization. I couldn’t have phrased it any better. I love how you also went through really what’s included in the program, right? If anybody’s curious about what do we talk about the program, because I mentioned earlier, this is not a technical program, not to talk about tools, although there was a specific module where we talk about tool name, but that’s even like in the latter part.

There’s a lot that comes into the implementation of AI. And the thing is CS leaders are being asked, what are we doing with AI? And I do hope that this program helps CS leaders have that playbook because nobody has written any playbook. We’re all figuring this out as we go along, right? And so I truly appreciate you sharing your experience so openly, Dee. Thank you for taking the time to join me today. I appreciate your perspective. And I know this conversation is going to be valuable for so many customer success leaders who are trying to make sense of AI and what it actually looks like to apply it in a thoughtful and practical way. And for those of you listening, if this conversation sparks something for you and you’re curious about joining a future cohort of the AI for CS leaders executive bootcamp, I’ll be sharing more details once enrollment opens up. Thanks so much for tuning in, and I’ll see you in the next episode.