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Check it OutPulse isn’t just a conference—it’s where innovation meets community. The largest gathering of professionals dedicated to sparking revenue growth, building real connections, and turning ideas into action. Ready to put customers at the heart of your strategy? This is the place.
Check it OutA practical blueprint to help customer success managers (CSMs) master artificial intelligence (AI) and unleash their own potential
Artificial Intelligence (AI) is a revolutionary technology that has transformed the world of business. Software as a service (SaaS) companies have taken the lead in AI adoption, updating their business models to account for the power of AI to increase productivity and drive profitability. And forward-thinking professionals across the tech sector have realized that AI enhances their ability to contribute—and advance their careers.
But because this new technology is such a game-changer, it has become difficult to differentiate between hype and reality when it comes to the role of AI in the workplace. Some have compared AI to the invention of fire or the wheel, while others fear that AI is going to take their jobs. The truth is, there is no need to make hyperbolic claims about AI—the real world impacts are already clear. AI has become table stakes for building efficient, sustainable SaaS organizations in today’s market.
In Customer Success (CS), the use of AI is growing fast. The recent State of AI in Customer Success Report from Gainsight found that 52% of CS orgs are using AI. But interestingly, AI is still primarily a “bottom-up” tool that employees are using for their own personal productivity. In most cases, CSMs are taking the initiative to learn how to use this valuable tool, rather than waiting for a mandate from on high.
That’s because AI empowers CSMs to enhance their efficiency and their impact so that they can craft more engaging and personalized customer experiences. It’s clear that AI is advancing the role of CS as a discipline—while raising expectations for individual CSMs.
Not knowing AI is not an option. The world is changing. In a year or so, if you don’t know how to leverage AI, you will probably not have a job.
At Gainsight, we’ve seen firsthand how AI can level up CS teams—and become a force multiplier for CSMs. We’ve taken those learnings and written this ebook to help CSMs get a running start with AI. You’ll learn the fundamentals—how AI works and how it can solve the biggest challenges that CS faces. Then we’ll give you clear steps on how to go from zero to 100 with your AI skills. Finally, we’ll show you some practical use cases that you can start executing right away.
Let’s get started!
Customer Success teams are operating in a transformed market. Instead of prioritizing rapid growth, SaaS companies now focus on building sustainable customer relationships. This strategic change has placed CS front and center as leaders in the effort to renew and expand existing customers. What some may not realize is that emergence of AI actually dovetails perfectly with the strategic goals of CS. AI offers powerful tools for this new reality.
Churn, retention, expansion. AI excels at spotting hidden signals in customer behavior that humans might miss. For churn prevention, it detects subtle combinations of declining usage, delayed responses, and reduced feature adoption—often months before visible red flags appear. With retention, AI identifies what successful long-term customers have in common, from their onboarding journey to their usage habits. For expansion, it recognizes behavior patterns of customers just before they upgrade, helping CSMs time their conversations perfectly.
Cross-functional collaboration. AI transforms cross-functional collaboration by surfacing customer insights relevant to each team: showing Sales which features drive the most value; helping Product prioritize improvements based on usage patterns; and enabling Marketing to spotlight actual customer success stories with real time knowledge of the customer sentiment. This shared, data-driven view eliminates siloed decision-making and helps teams align around customer outcomes.
Understanding customers and personalizing engagements. Generative AI transforms how CSMs understand and engage customers by synthesizing multiple data points—from success metrics to support tickets to stakeholder communications—to identify each account’s unique pain points and objectives. CSMs can then leverage these insights to create tailored success plans, customize check-in agendas based on actual product adoption, and proactively share relevant best practices from similar customers who’ve achieved their goals.
Doing better with less (impact AND efficiency). AI enables CSMs to simultaneously increase efficiency and deepen customer impact. While it handles time-consuming tasks like health score monitoring and email drafting, CSMs can focus on high-value activities—using AI-powered insights to solve strategic challenges, identify emerging customer needs, and build proactive success plans based on predictive analytics. The result is more meaningful customer engagements, not just faster ones.
The AI hype cycle led people to believe AI would transform everything overnight. AI is transformative, but even as fast as it’s moving, we have to remember there’s a learning curve. We’re still getting smarter about how to best use it as a tool for improving customer success.
At Gainsight, we champion a human-first approach to the adoption of AI. Customer relationships are at the heart of what CSMs do, so we want to use AI to enhance those human connections. We have identified four key areas where AI drives human-led excellence in CS.
AI helps CSMs identify risks earlier by automatically tracking a much wider range of inputs and data than was possible before, looking at emails, support tickets, customer conversations, telemetry data, engagement, and more.
AI can even read and extract human emotions from customers, not just in one-on-one interactions but also in community, webinars, and office hours. That gives CSMs the ability to see and understand sentiment across the entire scope of the customer relationship.
AI can also discover unexpected correlations that previously would have required a data scientist analysis, which is going to give health scores a major makeover.
The result is that AI eliminates blind spots and becomes the eyes and ears of CSMs. They will be operating with deeper insights and emotional intelligence, which will ultimately lead to proactive rather than reactive customer success strategies.
AI-powered automation—like AI-generated meeting summaries, writing assistance, and automated reports on customer health—significantly reduces the amount of time CSMs need to spend on manual administrative tasks, like data entry. AI also enables CSMs to create polished, CS-specific assets such as emails almost instantaneously.
All that extra time lets CSMs focus on more strategic objectives and deliver customer value. But it’s more than just an efficiency play. Conversational AI also helps CSMs better at mentally taxing strategic work. For example, a conversation with AI can help CSMs develop really incredible discovery questions going into a customer call.
And while AI has many impacts at a tactical level, it also helps overall CSM performance. A recent Gainsight survey found that CSMs who use AI are better at overcoming immediate challenges, extending their skill set, making better decisions, and feeling more confident in their roles. The overall result is that CSMs are empowered and impactful—AI is redefining the CSM role from task-juggler to strategic advisor.
Conversational AI has a number of team-building benefits.
Making tons of customer data easily accessible through AI, CS and other customer-facing teams can find answers from among shared knowledge quickly, providing better and quicker customer responses and value, as well as facilitating more impactful and meaningful internal relationships.
Conversational AI also drives continual learning and self-development, with AI as an expert coach. AI is a goldmine of information about a customer’s products, their business goals, their industries, and the roles and career stories of key customer contacts. It’s like having a strategic thinking partner who helps elevate every customer interaction.
And as AI-based tools like GPTs are incorporated into CS workflows over time, the cumulative expertise and knowledge will form a foundation of wisdom for other team members in the future.
Being a CSM is all about being customer-centric. AI has the power to enable CSMs to be more attentive to customers than ever before. By spending less time on mundane tasks they can be more attuned to customers during interactions.
But they will also be better prepared behind the scenes by utilizing the research capabilities of AI, gaining helpful industry knowledge about trends, industries, and business topics.
Conversational AI enables CSMs to zero in on specific customer details, saving them time and helping them deliver a more personalized customer experience.
AI also powers improved self-service for customers, who will be able to access more information through Community and other channels.
Whether a new user is learning ChatGPT or any other AI tool, the experience will be similar in that they are learning a brand new skill. Perhaps the biggest challenge for CSMs is that they need to create new use cases instead of following an existing playbook. In short, they need to become inventors. The good news is that we have identified a five-step development process that CSMs can follow on the path toward innovating with AI.
Learning any new skill can be intimidating, but AI is especially challenging because it is so open-ended. At this stage, everything is new, and CSMs should adopt the Shoshin model, which is the beginner’s mind. CSMs should focus on following instructions and absorbing as much as they can.
The goal of this stage is to become literate with AI. Go slow and start with basic questions. What is a Large Language Model (LLM)? What is a GPT? What is machine learning?
During First Flight, CSMs should work in a safe space where it is ok to make mistakes. This can be uncomfortable in a work context where competence is so important. So instructors need to reassure participants that they won’t be judged.
During the First Flight phase, training should focus on education about AI basics. A good place to start is explaining the difference between using an LLM vs using a search engine. While they “whys” are important, most of the emphasis should be on practical knowledge that a user would need to operate ChatGPT or another Gen AI platform.
At this stage, the goal is to get “just enough information to be dangerous.” CSMs should learn the basics by doing. Once they have experience using AI, they can apply those learnings to any AI tool.
CSMs should explore the features of multiple AI tools if possible, including ChatGPT and a CS-focused AI tool like Gainsight. Because AI is such a novel technology, the user interface that people will experience when exploring an AI tool will be different from what they are used to, and it may not be as intuitive. Live demos, simple exercises, and how-to-AI frameworks are all useful exercises here.
CSMs should be doing hands-on work for themselves, but with an expert in the room who can provide explanations as needed.
During Catching Air, training should move from education to exercises that give CSMs a chance to practice certain Gen AI skills. For example, to teach CSMs how to refine a prompt in Gen AI, provide a hypothetical situation, such as preparing to attend a conference. Start with a simple prompt: “I’m at Gainsight’s Pulse conference, how do I make the most of the week?” Then have CSMs refine the prompt and explore what Gen AI can do.
At this stage, dedicated inventors begin to self-select while more casual AI users tend to fall away. Metamorphosis is all about cultivating creativity and curiosity, which are innate human abilities, but they need to be unlocked. CSMs should be growing and learning here.
Here, CSMs move beyond the basics and start asking “what if” questions. The instructor should model curiosity in prompting, but make sure it is grounded in usefulness. For example, trainees could train the AI to write in their unique voice (see Skills in Focus for more on that use case).
This stage is about creating space for personal epiphany. It should be a combination of group and individual practice, with the instructor delivering the right mix of instruction, scaffolds, and bumpers. Having the CSMs share ideas with each other will accelerate their growth.
In the Metamorphosis stage, CSMs should use the skills they learned in the previous stage and begin to experiment. For example, once they have mastered the skill of writing a prompt to receive the information they need, they can start adding instructions that will make the output more useful. If the company’s brand voice is “childlike joy,” CSMs can begin looking for ways to instruct Gen AI to produce the right tone with its responses.
Now, CSMs are ready to move beyond pure learning and create something useful for the first time. The message is: You want it? You make it.
The focus should be on creating a tactically useful invention, such as a GPT. Once a CSM has decided on their goal, there should be a short period of instruction, followed by use case ideation exercises and lots of experimentation. For example, CSMs should try using different input and output formats in the AI, such as turning an email into a slide deck or a blog post into a newsletter.
This stage is best executed in a peer-to-peer space with lots of collaboration. Cross-talk will help them to develop their inventions.
During Alchemy, CSMs should focus on building a use case that their company will actually use in day-to-day operations. If you are using Chat GPT, CSMs should create a custom GPT that anyone on the Customer Success team could use to improve an existing process. For example, a CSM could create a Ghost Writing tool that captures the voice of their company’s executive leadership team. Emails or other communications sent with the “executive” voice can help build stakeholder alignment with executive sponsors at an account.
Now, CSMs are ready to start delivering actual business value for their companies using AI. They should be thinking about how to incorporate AI use cases into processes and workflows.
Inventor CSMs should be creating real use cases for the company. As use cases are refined, the group should start thinking about how to grow and scale the utility of AI beyond the core team. Timeline templates, playbook tasks, and success plans are all great places to focus.
At this advanced stage, leaders should create pods for dedicated teams to collaborate, share, and innovate how to do their work better with AI.
At this stage, CSMs should start examining how they can use Gen AI to scale across the Customer Success team and beyond. For example, how can you use Gen AI to create a Success Plan? This work should definitely take place within a team context.
As CSMs go through the AI training process, there are some fundamental skills they should be learning.
We are all accustomed to interacting with the Google Search box, so most people start using AI as if it were a search engine; however, LLMs are meant to be used differently. Instead of making a request for information, you are starting a conversation with the tool.
The back and forth with the AI tool (sometimes called “ping-ponging”) is designed to stimulate curiosity. In other words, the AI tool is not built to give you a single definitive answer on the first try. The intention is to keep refining and expanding your queries so that you fully explore the topic that interests you.
Remember that LLMs are trained on almost all of the data that’s accessible and free in the world. You need to use the conversation to set some parameters and put blinders on the AI to help guide it.
When you use an LLM, you can program a set of custom instructions or preferences. These settings let the AI know how you like to work so that you are not reinventing the wheel every time. For example, you may value succinct, clear communication from the AI that avoids redundancy. You can set a tone of voice for the AI—for example, you can infuse the AI’s output with fun, humor, wit, kindness, or sarcasm.
Asking an AI agent a simple question is the most basic way to use the tool. Creating agents and GPTs is a more sophisticated and effective method to generate rich, useful content. For example, you can
Instead of using raw AI content, which will be generic, you will want to create your own voice. You can do this by feeding the AI agent examples of your own writing, such as Slack messages, emails, newsletters, etc. The agent will analyze the tone, style, and structure of your writing. The AI agent will effectively become your ghost writer and will respond to your conversations in your voice, with content you can use and be distinctive as yours.
Once they have good familiarity with how to use AI, here are some core tasks that CSMs will use in the course of their day-to-day work.
Generation. AI is a great tool for generating text for any purpose. CSMs can use AI to elevate their writing, refining their overall communication, and making both internal and external messages clear and strategically aligned with their company and their customers.
Here are some examples of prompts you could use to generate useful content with Gen AI:
Summarization. AI can be used to automatically create summaries from meeting notes, calls, internal updates, or other sources so CSMs can quickly find the information they need. This will make CSMs more efficient and allow them to focus more attention on their customers.
Here are some examples of prompts you could use to create summaries using Gen AI, including how to create a summary from multiple conversations:
Q&A. Working with a conversational AI agent can help CSMs answer client questions in real time. They can even give a customer direct access to the AI agent to facilitate self-service.
Here are some possible Q&A prompts that you could use with Gen AI:
Extraction. When dealing with documents and other dense forms of data, AI can construct comprehensive reports and extract actionable insights from data.
Here are some prompts for specific use cases for leveraging Gen AI to extract data:
Classification. AI can be used to classify cohorts or information into different buckets so that CSMs always know where to find the most accurate and up-to-date information.
Here are some examples of Gen AI prompts used to classify information:
Ready for a real world example of AI in action? Using AI to handle a meeting can be a quick win for any CSM getting started with AI. After you do it once, you’ll never go back, and you’ll feel like a real AI pro.
The scenario: One of your hard-to-reach accounts has finally scheduled a business review—after a year! You have one day to prepare for the meeting. And renewal is right around the corner, so you need to follow up fast. Here’s how you can use AI to meet this challenge head on.
Given the large amount of information about this customer, you could easily spend hours or even days reading through all relevant information. Instead, using AI, you can create a concise summary of a customer’s key milestones, risks, and goals using data from your company’s CS platform.
Your information sources include product usage data, customer health scores, and summaries of every interaction that has taken place between the customer and the company over the past year.
And because you assembled the information so quickly, you can send the report to your teammates and executives in advance of the meeting. Now, everyone on the internal team is aligned and ready to deliver an amazing customer experience.
The team assembles for a customer-centric meeting, during which AI enables you to avoid the distraction of note-taking. Your AI tool instantly summarizes the entire call and even performs a sentiment analysis of the customer’s voice to identify risk. But the best result is that you are present and effective during the meaning, conducting a meaningful conversation with a customer that truly adds value. You are really focused on asking the right questions and making sure you’re getting the information you need from the customer to build the relationship.
Instead of spending hours that night or during the following day creating a summary and follow-up communications, AI automation enables you to tackle this task in minutes. AI helps you to generate quick, accurate, and thorough emails for the customer that clearly outline next steps (recommended by the AI). You also send out AI-generated communications to internal stakeholders to gain alignment around customer health and status. Finally, AI automatically adds information about the call into your CS platform. The entire whole follow-up process has completely transformed.
The impact of AI also goes beyond the meeting itself. Successful meetings with high-quality customer interactions help you build a deeper relationship with each of your customers. You have more time to customize your efforts to match the specifics of each of your customer’s journeys. And because you are not spending your days on manual follow-ups and finding answers for customers, you actually have time to schedule more face-to-face meetings.
Change is always difficult, and despite the obvious advantages of AI, organizations seeking to adopt these technologies may encounter a number of barriers. As individual contributors, it may not be the responsibility of CSMs to overcome these barriers. But being aware of them should help CSMs navigate the changing landscape and help to standardize the use of of AI in CSM workflows.
Lack of internal expertise: Even though it is growing rapidly, AI is still a relatively immature technology. Companies see lack of experience and expertise as a barrier to broadscale adoption and value creation, which may block internal enablement. Training up CSMs on AI skills can help overcome this barrier.
Integration complexities: Integrating AI into existing processes is not always straightforward, especially for organizations that rely on legacy systems and processes. To successfully adopt AI, CS teams will need to work closely with IT partners along the way, so the more out-of-the-box capabilities they have the better.
Data privacy concerns: The majority of companies have not yet produced solid data compliance policies around AI, so CS—and other teams—are often nervous to formally roll out the use of a new technology, especially one that could use customer data without corporate approval. The good news is that security protocols for AI have already advanced by leaps and bounds.
Output reliability: AI relies on large language models (LLMs) and other data pools to function, which means that your AI tools are only as good as the data inputs that go into them. CSMs have to be able to trust the results of their AI, so thought and effort have to be put into ensuring that they have high-quality data.
Resistance from the team: Change management is hard and there is always resistance to change. AI requires CSMs to learn new skills and step outside their comfort zone. There may also be fears that AI is somehow a replacement for CSMs. While those fears are understandable, they are unfounded, and CSMs who embrace the change will thrive in the new AI world.
There is a lot of unknown and uncertainty around AI, but there is also so much excitement. We need to lean into change, especially in the workplace.
Ready to revolutionize your CS game? The AI revolution isn’t just knocking at the door – it’s already transformed how we work, think, and deliver value to our customers.
Throughout this guide, we’ve cut through the AI hype to give you the real deal:
But here’s the thing: AI isn’t just another tool in your toolkit—it’s your partner in creating exceptional customer experiences. Think of it as your personal CS multiplier, amplifying your expertise and intuition while freeing you to focus on what truly matters: building lasting customer relationships.
The future of CS isn’t about AI replacing CSMs—it’s about the CSMs who embrace AI outshining those who don’t. Your customers win with better service, your company wins with stronger relationships, and you win by becoming an irreplaceable force in customer success.
It is time to take that first step and transform from a CS professional to a CS innovator.
Welcome to the future of Customer Success—let’s make it extraordinary.
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