# CS in the AI Era > Bi-weekly thinking for CS leaders reinventing Customer Success as a revenue function. AI-era frameworks. No fluff. No generic advice. Every other Tuesday. Public Ghost content for AI and LLM tooling. This file includes a bounded export of public pages first, then recent public posts. Append `.md` to any post or page URL to get the content in Markdown (for example, `/example-post.md`). ## Pages ### Hi, I'm Iliyana! URL: https://csintheaiera.com/about/ Last updated: 2026-06-21T15:23:55.000Z I left Bulgaria at 19 with a suitcase and a plan that changed about twelve times after that. Germany, the UK, Ireland, the Netherlands, Spain — six countries, five languages, and one consistent brief in every role: take something that doesn't exist yet and make it work at scale. While building programmes and leading teams during my time at HubSpot, Cisco and ServiceNow, I became completely convinced that Customer Success is the most misunderstood function in SaaS. Here's what twelve years taught me: CS has a brand problem. It gets positioned as the relationship team, the renewal team, the make-customers-happy team. Meanwhile the CFO is asking why it exists on the P&L. AI is changing that — not because it's magic, but because it's forcing CS leaders to finally answer the question boards have been asking for years: what is this function actually worth? CS in the AI Era is my answer. A newsletter and community for CS leaders who are done being the nicest team in the room and ready to be the most valuable one. I write every Tuesday. I live in Jerez de la Frontera with my husband, our two daughters, and an unreasonable amount of ambition. Everything I publish has genuinely earned its place in my week. ![](https://storage.ghost.io/c/1c/51/1c51e81c-2aaf-4cd5-8902-62fcb42ea145/content/images/2026/06/Iliyana-Stareva-6.png) ## Sign up for CS in the AI Era From relationship managers to revenue leaders Subscribe Email sent! Check your inbox to complete your signup. No spam. Unsubscribe anytime. ### Newsletter URL: https://csintheaiera.com/newsletter/ Last updated: 2026-06-21T18:36:01.000Z Bi-weekly thinking for Customer Success leaders reinventing CS as a revenue function. ## **What you get:** - Practical frameworks for leading CS through the AI transition - Revenue language you can bring to your executive team - No fluff, no US-centric benchmarks, no generic CSM advice Published every other Tuesday. Written by Iliyana Stareva — EMEA CS leader, published author, 12 years in enterprise SaaS. Free to read. Paid tier unlocks deployable tools, frameworks, and prompt libraries. ## Sign up for CS in the AI Era From relationship managers to revenue leaders Subscribe Email sent! Check your inbox to complete your signup. No spam. Unsubscribe anytime. ### Book Iliyana to Speak URL: https://csintheaiera.com/speaking/ Last updated: 2026-06-21T16:03:07.000Z 30+ events across 15+ countries. Topics: CS leadership in the AI era, reinventing CS as a revenue function, executive leadership and org design. Iliyana doesn't do motivational keynotes. She brings frameworks, data, and sharp thinking to audiences who want to understand what leading CS actually looks like when AI changes everything. ### Signature topics: **1\. CS in the AI Era: How to Lead the Shift Before It Leads You** - For CS leaders navigating AI transformation in their teams and functions. **2\. From Cost Centre to Revenue Engine: Redesigning CS for Growth** - For CCOs, CROs, and CS VPs making the commercial case for CS investment. **3\. The European CS Leader's Playbook** - For EMEA-based leaders operating inside US-headquartered SaaS companies. Available for keynotes, panels, podcast appearances, and corporate events. Based in Spain, available across Europe and virtually. *To enquire, email iliyana@csintheaiera.com* ### Privacy Policy URL: https://csintheaiera.com/privacy-policy/ Last updated: 2026-06-22T09:12:10.000Z *Last updated: June 2026* **Who we are** CS in the AI Era is a newsletter and online publication run by Iliyana Stareva. If you have any questions about this privacy policy or how your data is handled, contact us at [iliyana@csintheaiera.com](mailto:iliyana@csintheaiera.com). **What data we collect** When you subscribe to CS in the AI Era we collect your email address and, if you choose to provide it, your name. We do not collect any other personal data. **Why we collect it** We collect your email address for one purpose only: to send you the CS in the AI Era newsletter. 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Any changes will be posted on this page with an updated date. **Contact** For any privacy-related questions: [iliyana@csintheaiera.com](mailto:iliyana@csintheaiera.com) ## Posts ### Your Health Score Is Green, but Your Account Is About to Churn. Here's Why. URL: https://csintheaiera.com/your-health-score-is-green-but-your-account-is-about-to-churn-heres-why/ Last updated: 2026-08-04T06:00:04.000Z Progress on the QBR slides looks on track; the account has a green health score, 85% on product adoption and no open escalations. The renewal is in three months and nobody is worried. Suddenly, the customer's CFO restructures the organisation. The VP of Operations who championed the implementation, who'd fought for the budget, trained the team, and got the product live, is now gone. And nobody on the vendor side had noticed the VP stopped attending the monthly syncs six weeks earlier. So the account churned. Green health score right up until the termination notice. I've seen this happen at HubSpot, at Cisco, and now at ServiceNow. The post-mortem is always the same: the score didn't fail because the data was wrong. It failed because a single number was never designed to capture what actually precedes churn. What precedes churn isn't a just red score. It's a pattern of quiet signals: specific, observable, almost always visible in your data 60, 90, 180 days before the conversation you don't want to have. Standard health models don't surface them. It's other signals that often have a stronger effect on the renewal. Here are six I've seen most consistently, and what to do when you spot each one. ## **The 6 Silent Churn Signals** **1\. Executive sponsor disengagement** Your champion stops attending meetings, maybe not dramatically, they just start sending delegates. In your CRM, meeting attendance looks fine because the account still shows activity, but the person who owns the internal budget justification has quietly stepped back. *What you need to start tracking*: Flag any account where the named executive sponsor hasn't joined a meeting directly in 45 days. Don't wait for the CSM to notice; build the alert. **2\. Champion exit and who replaced them** This is the one that kills the most renewals and almost no health model catches it. Your champion leaves the company. A new decision-maker comes in from outside - often from a competitor, sometimes from a company where they used a different tool. They have no relationship with you, no institutional investment in the product, and they're three months into a new role where proving their own value matters. At ServiceNow, we learned to treat any champion departure as a commercial trigger, not just a relationship task. The new stakeholder's background matters. Where did they come from? What tools did they use there? Have they already mentioned anything about "evaluating the current stack"? That's not curiosity; it's due diligence for a decision they've already started making. *What to do*: The moment a champion exit is logged, run a stakeholder mapping exercise and assign an exec-to-exec introduction within 30 days. If you don't have exec coverage at that account, you will have a tricky renewal when the time comes. **3\. Adoption plateau after onboarding** Usage hits a ceiling at month three or six and stays flat. Standard models read this as stable. What it really means is this: the customer implemented enough to justify the initial purchase, but never reached the use cases that would justify renewal - meaning the intended value. Logins might be consistent; they're just not doing anything meaningful. *What you need to start tracking*: Build a depth-of-use metric alongside your adoption rate. If the same three features account for 90% of activity at month six, that account is a contraction risk regardless of what the score says. **4\. Support ticket topic shift** Watch what customers are asking, not just how many tickets they raise. When tickets shift from "how do I do X" to "why doesn't X work" or "we need X exported," the product is hitting its ceiling for their use case or something was done wrong. In isolation, a spike in support volume looks like engagement; in reality, it's a customer preparing the business case for switching. *What you need to start tracking*: Tag support tickets by intent: how-to, product limitation, data export. If limitation and export tags are trending up in an account 90+ days before renewal, flag it for a proactive conversation. **5\. Silence after a product change** A major feature launch or pricing change goes out. Some customers light up; they ask questions, they test, they engage. Others go quiet. A customer who doesn't react to something you expected them to care about has usually already started reviewing their options. *What to do*: For any product change that affects your top 20% of accounts by ARR, build a 14-day response check into the playbook. No response is data - treat it as one. **6\. Stakeholder map erosion** Six months ago, five people at this customer were actively engaged with your product. Now you have two: both in operational roles, neither in a position to make or influence a renewal decision. No one left the company, they just stopped being involved. By the time the renewal conversation starts, there's no internal champion to run it on your behalf. *What you need to start tracking*: Map stakeholder engagement by seniority, not just headcount. Breadth of contacts isn't the same as depth of coverage. An account that narrows to operational-only engagement is already at risk. None of these signals are exotic. Every experienced CSM recognises them the moment they're named. The problem isn't awareness; it's that standard health models don't track them systematically, so they exist only in the CSM's head - invisible to the forecast, invisible to leadership, invisible until the termination notice. The health score had one job: tell you which accounts need attention. For years it's been doing something else - telling you which accounts looked healthy when someone last updated the model. According to the 2026 State of Customer Success report, 60.7% of CS teams review their health scores on an ad-hoc basis or never. [That's not a tooling problem, but a design problem](https://csintheaiera.com/reactive-customer-success-has-a-price-tag-most-cs-leaders-just-dont-know-what-it-is/). The leaders who survive the next efficiency wave won't be the ones with the most sophisticated score. They'll be the ones who stopped using a number to do a system's job. The six signals above are your team's job to catch. But there's a prior question that only you, as a leader, can answer: does your current health model even give them the infrastructure to catch them? Pull up your health score logic this week. Ask three things: 1. Is executive sponsor engagement tracked as a named, dated field or inferred from general account activity? 2. Does a champion exit trigger a commercial escalation, or just a CRM update? 3. When was the model last rebuilt against actual churn data from your portfolio? If you can't answer all three cleanly, you don't have a health system. You have a dashboard that's giving your board false confidence and giving your team false cover. That's the conversation to have with your CRO before the next QBR, not after the next churn notice. Which of these six signals would your current health model catch automatically and which one would only surface because a CSM happened to mention it in a call? — Iliyana --- *CS in the AI Era is a bi-weekly newsletter for Customer Success leaders in European SaaS. If someone sent this to you and you want to receive it directly,* [*subscribe here*](https://csintheaiera.com/reactive-customer-success-has-a-price-tag-most-cs-leaders-just-dont-know-what-it-is/#/portal/signup)*. Or if you know* a *CS leader who should read it? Forward it.* ### Reactive Customer Success Has a Price Tag. Most CS Leaders Just Don't Know What It Is. URL: https://csintheaiera.com/reactive-customer-success-has-a-price-tag-most-cs-leaders-just-dont-know-what-it-is/ Last updated: 2026-07-21T11:41:20.000Z *The leaky bucket was always there. We just never counted the water.* In every company I've worked at — HubSpot, Cisco, ServiceNow — some version of the same conversation happened: a customer is about to churn, the CSM and AE are surprised, escalations begin, and leadership gets involved. Someone says we should have caught this earlier. And then we move on to the next fire. The leaky bucket has a name in CS. What it rarely has is a number. That's the problem I want to fix in this issue — because the "we need to be more proactive" conversation has been happening in CS for a decade, and it's still not working. Not because CS leaders don't believe it, but because they haven't had the financial language to make anyone else believe it too. ## **What reactive CS actually costs** Reactive CS doesn't look like failure; it looks like effort. It looks like a full Slack channel, a packed escalation call, a CSM who stayed late to rescue a renewal. It feels heroic in the moment, but it's compounding financial damage in aggregate. The model most CS orgs are still running is essentially this: wait for a signal bad enough to be unmissable, then deploy people and executive time to contain it. The customer either stays or churns. Move on. The economics of that model are worse than most boards realise and most CS leaders can't articulate why, because they're measuring activity rather than cost. There are five places where reactive CS leaks money — not metaphorically, but structurally. **1\. Forecast instability** When you don't know which accounts are at risk until they tell you, your GRR forecast is a guess dressed as a number. Every quarter, CS leaders present renewal confidence based on incomplete signals; finance then builds revenue plans on top of that. When the forecast misses — and reactive CS organisations miss more often — the cost isn't just the lost revenue. It's the credibility hit that makes every subsequent forecast harder to defend. **2\. Expansion delay** The accounts most ready to expand are almost never the ones getting the most CSM attention in a reactive model. The accounts getting the most attention are the ones on fire. Which means expansion conversations happen late, if at all; the CSM is too busy fighting yesterday's problem to build tomorrow's revenue. A single quarter of expansion delay across a €5M book of business is a number worth putting in front of your CRO. **3\. Escalation overhead** An executive escalation costs more than it looks. There's the CSM time, the CS leader time, the executive sponsor time, the involvement of Sales, Product, Support — sometimes Legal. One serious escalation can consume 30–40 hours of senior time. Multiply that by the number of escalations your team handles in a quarter and the number gets uncomfortable quickly. **4\. CSM burnout and attrition** Reactive CS organisations have higher CSM turnover. The correlation is consistent enough that I'm confident stating it: CSMs who spend the majority of their time firefighting — rather than building relationships, running strategic conversations, and seeing accounts improve — burn out faster. Replacing a CSM costs ca. 50–75% of their annual salary when you account for recruiting, onboarding, and the productivity gap while the new hire ramps. That's a people cost most CS budgets don't track explicitly. **5\. Sales trust erosion** This one is harder to quantify but the most strategically damaging. When CS can't reliably identify at-risk accounts before Sales hears about it from the customer, the relationship between CS and Sales degrades. Sales stops looping CS in early, CS gets less context on new accounts and the handoff quality drops. It becomes a self-reinforcing problem and it makes cross-sell and upsell motions significantly harder to execute. The commercial impact is real even if no one has put a number on it. ## **Why my function exists** Part of the reason Customer Health Assurance exists at ServiceNow and why it was created as a distinct function is that the traditional CS model wasn't catching problems early enough. We were operating in the reactive window, not the preventive one. Since we've been running a more structured, signal-based approach, we've contributed to a few points improvement in GRR. A few points might sound modest, but at enterprise scale, a few points of GRR is significant — both to the revenue line and to the valuation multiple, since net revenue retention is one of the primary metrics investors and boards use to assess the health of a SaaS business. What made the difference wasn't more CSMs and it wasn't a better health score dashboard. It was systematic signal capture — alerts that fire when something even remotely begins to feel wrong: a drop in product engagement over a few weeks, a piece of news suggesting the customer is going through a restructure, a pattern of declining meeting attendance. Not red flags but early yellows. The alternative to reactive isn't just proactive. It's systematic. ## **The Reactive CS Cost Model** If you are struggling to move your CS org from reactive to proactive, it's often because you don't have internal buy-in. And as always in big organisations, if you want something to change, you need to first build the business case. Here's how you can do it in this instance. Just note, the goal isn't a precise figure — it's a defensible estimate that shifts the conversation from "we should be more proactive" to "here's what not being proactive is costing us." Run these five calculations for your current book of business: 1. **Forecast variance cost** — What was your GRR forecast vs actual over the last four quarters? Multiply the variance by your average contract value. That's your forecasting miss in revenue terms. 2. **Expansion delay cost** — How many accounts had expansion conversations that started in the second half of the year rather than the first? Estimate the NRR impact of those conversations happening one quarter earlier. 3. **Escalation overhead** — Count your executive escalations last quarter. Multiply by a conservative estimate of senior time (15 hours per escalation × blended hourly cost of people involved). This is a real cost most CS orgs don't track. 4. **CSM attrition cost** — How many CSMs did you lose in the last 12 months? Multiply by 60% of their average annual salary. That's the replacement cost floor. 5. **Sales trust deficit** — Harder to quantify; use this as a forcing question instead. When did Sales last come to CS proactively before a deal was at risk? If the honest answer is "rarely," the cost is buried in pipeline and expansion metrics you aren't attributing correctly. Add the five numbers. The total is almost always larger than the investment required to build a proper signal-based health system. That's the number you bring to your CRO. **The prompt for this issue** *"I want to build an internal business case for moving from reactive to proactive, signal-driven CS. Help me estimate the cost of our current reactive posture using these five leakage points: \[paste your numbers or estimates\]. Then help me draft a one-page executive summary I can bring to my CRO."* Run it in Claude or your AI of choice. Use the five calculations above as your inputs. The output won't be perfect — but it will be specific, and specific is what moves budget conversations. Or, I've built this as a working Notion template so you can fill it in against your own book of business. It takes about 20 minutes. The link is below — free, no gate. The output is a number you can bring to your next CRO conversation. ![](https://storage.ghost.io/c/1c/51/1c51e81c-2aaf-4cd5-8902-62fcb42ea145/content/images/2026/07/Screenshot-2026-07-20-at-14.47.11.png) A five-point leakage audit to quantify your reactive posture — and build the internal business case for changing it. [Open the Reactive CS Cost Model in Notion ](https://app.notion.com/p/The-Reactive-CS-Cost-Model-Leakage-Audit-Template-3a3f52ce3a4b8145acc5c557ff7e0809?source=copy%5Flink) How have you made CS more proactive? — Iliyana *Next issue: Your health score is green. Your account is about to churn. Here's why — the five silent signals that appear 60–90 days before churn and almost never show up as red in standard health models.* --- *CS in the AI Era is a bi-weekly newsletter for Customer Success leaders in European SaaS. If someone sent this to you and you want to receive it directly,* [*subscribe here*](https://csintheaiera.com/the-part-of-cs-that-ai-is-replacing-and-the-part-it-cant-touch/#/portal/signup)*. Or if you know* a *CS leader who should read it? Forward it.* ### The part of CS that AI is replacing. And the part it can't touch. URL: https://csintheaiera.com/the-part-of-cs-that-ai-is-replacing-and-the-part-it-cant-touch/ Last updated: 2026-07-20T12:27:40.000Z *The fear isn't irrational. But most CS leaders are drawing the wrong conclusion from it.* --- There's a conversation happening in every CS org right now. Sometimes it's explicit — a leadership team deciding which CSM roles to backfill after a restructure and quietly concluding they don't need to. Sometimes it's a budget review where someone asks whether AI can cover the renewal narrative work that used to take a senior CSM three hours per account. Sometimes it's just a feeling — a creeping sense among CS professionals that the role they built their career around is being quietly hollowed out from underneath them. [The 2026 State of Customer Success report](https://www.customersuccesscollective.com/state-of-customer-success/?ref=csintheaiera.com), just released by the Customer Success Collective, confirmed what many of us have been sensing: 44% of CS professionals have been at their current company for two years or less — a 26-point jump from 2025\. That's not a hot talent market moving people upward. That's restructuring, GTM resets, and experienced people who watched the operating model change underneath them and decided to leave. I've been in and around this industry for over a decade — at HubSpot, Cisco, ServiceNow — and I don't think the fear is irrational. But I also think a lot of CS leaders are drawing the wrong conclusions from it. They're either catastrophising (AI is coming for all of us) or dismissing (relationship work can never be automated). Both of those positions are wrong and both will cost you. What I want to do in this issue is draw the actual line. --- ## What AI already owns Let me start with the task I mentioned in [Issue 01](https://csintheaiera.com/customer-success-is-not-broken-the-job-description-is/) — the one that consumed more of my time than I'd like to admit: gathering data and information about the health and state of an account before a customer conversation. Every CS leader knows this motion. You have a meeting in an hour. You need to know where the account stands — usage trends, open support tickets, recent engagement, contract terms, last QBR output, any outstanding adoption or risk flags. In a well-instrumented organisation, that's still a 30–45 minute exercise. In a fragmented one — and the State of CS 2026 report tells us that 52.1% of CS teams say their customer data is fragmented across systems — it can eat your morning. AI does this now. Not perfectly and not without a clean data foundation (more on that in a future issue), but the synthesis layer — pulling signals together into a pre-meeting brief, drafting the renewal narrative, flagging risk patterns at scale — that's gone. It belongs to the machine. Here's the fuller picture of what sits on that side of the line: 1. Account health summaries and pre-meeting briefs 2. Meeting follow-up and action item capture 3. QBR deck population from existing data sources 4. Pattern recognition across cohorts — which accounts behave like accounts that churned six months ago 5. Product adoption reporting and anomaly flagging 6. First-pass churn prediction modelling 7. Renewal narrative drafts from usage and commercial data 8. Risk flag identification across a large book of business These are not edge cases. These are the tasks that occupy a significant portion of a CSM's week in most organisations. The 2026 State of CS data confirms it: AI is already present in CS workflows, but mostly at the productivity layer — email drafts, call summaries, quick research. Only 4.1% of CS teams are using AI for actual decision support: prioritisation, health scoring, risk assessment. Which means we're in a strange middle moment. AI is doing the prep work, but it's not yet trusted with the judgment calls. And the gap between those two things is exactly where the value of a CS leader sits. --- ## What AI can't touch A few months ago, I was preparing for what I expected to be a difficult commercial conversation. The signals were not great. The account had been quiet; usage was flat; the renewal was coming up. I walked in ready to defend the product's results. The meeting went somewhere else entirely. The leader on the other side of the call wasn't challenging our ROI. She was scared — about her job, about the restructuring happening inside her own organisation, about whether the investment she'd championed internally was going to survive the next budget cycle. She wasn't asking me to prove value. She was asking someone she trusted to help her think through what was happening to her. I listened and I asked questions. I shelved the commercial agenda for that hour and focused entirely on understanding what she was navigating. By the end of the call, we'd agreed on how I and the platform she'd invested in could help her make the case internally — not just for the renewal, but for her own role. No AI system built a relationship with that leader over the previous months. No AI read the pause before she answered my first question and decided to ask a different one. No AI had the judgment to recognise that this wasn't a negotiation; it was a human moment inside a professional context. That's what sits on the other side of the line and it's not just empathy — though empathy matters. It's commercial judgment built from human experience. The ability to challenge a customer's thinking when you know they're wrong, even when they're senior and they don't want to hear it. The ability to rebuild trust when a relationship has genuinely broken down. The ability to read a room and make a real-time decision about what the conversation actually needs. The 2026 State of CS report puts it plainly: 97.2% of CS professionals see CS as revenue-relevant. But 38% say revenue is handled by someone else — sales — and another 25.5% say CS owns renewals only. The gap between being revenue-relevant and being a revenue leader is not a data problem. It's a judgment problem. And judgment is not automatable. --- ## The CS Capability Map There's a framework I've been using to think about this clearly. I call it the CS Capability Map, and it has four quadrants. ![](https://storage.ghost.io/c/1c/51/1c51e81c-2aaf-4cd5-8902-62fcb42ea145/content/images/2026/07/CS_Capability_Map-CS-in-the-AI-Era.png) **Replace** — AI does this better and faster. Fighting it is career risk. Tasks here: account health summaries, renewal narratives, risk flag drafts, meeting prep briefs, churn pattern recognition, QBR population, adoption reporting. **Augment** — AI makes you significantly faster, but you're still in the loop. Tasks here: stakeholder communication at scale, playbook execution, onboarding coordination, commercial modelling, NRR forecasting, escalation management. **Elevate** — AI surfaces the signal; you're the one who decides what to do with it. Tasks here: at-risk intervention strategy, expansion opportunity qualification, executive relationship management, success planning, commercial prioritisation. **Protect** — Human-only, irreplaceable. The work that requires judgment, trust, and presence. Tasks here: board-level relationship building, crisis management, commercial negotiation, challenging a customer's internal decision-making, reading a room and changing your approach in real time, building the coalition inside a customer account that actually drives adoption. Here's the uncomfortable truth: most CS leaders are spending the majority of their time in Replace and Augment. The market is now paying — and increasingly, only paying — for the people who operate predominantly in Elevate and Protect. Where you spend your time is a strategic choice. Make it consciously. [![CTA Image](https://storage.ghost.io/c/1c/51/1c51e81c-2aaf-4cd5-8902-62fcb42ea145/content/images/2026/07/The-CS-Capability-Map-Self-Audit.png)](https://app.notion.com/p/The-CS-Capability-Map-Self-Audit-Template-395f52ce3a4b8148bd5ec5ebf78adbf6?source=copy%5Flink) I've made it easy for you and create a Notion template you can use right away to assess your CS capability map. Grab it below! [Get the CS Capability Map Template NOW! ](https://app.notion.com/p/The-CS-Capability-Map-Self-Audit-Template-395f52ce3a4b8148bd5ec5ebf78adbf6?source=copy%5Flink) --- ## The talent blind spot that's going to cost us There's a version of the AI-in-CS conversation that I see playing out in organisations right now, and it worries me more than any of the restructuring data. CS leaders are automating the Replace tasks — rightly so — and concluding that they no longer need as many junior CSMs. The efficiency case is real and the cost reduction is immediate. The problem is what we're actually destroying in the process. Seniority in people is only achieved by experience. The CSM who can hold a difficult executive conversation, read a room, make a judgment call under pressure — that person didn't arrive like that. They developed those capabilities by doing the work: writing the renewal narratives, building the pre-meeting briefs, sitting in the account reviews, making the early mistakes. Those "replaceable" tasks were also the training ground. When we automate the entry point, we cut the pipeline that produces the experienced CS leader in five years. We gain efficiency now and create a capability crisis later. The 2026 State of CS data signals this tension clearly. 66.8% of CS teams have no dedicated enablement function. 20.1% provide neither product nor sales training to their CSMs. One survey respondent described their onboarding as "sink or swim." Another said, simply: "We don't." AI makes this worse in an unstructured team, not better. As one expert in the report put it: you're handing powerful tools to people who were never taught the underlying motion. CS leaders who are serious about the Protect quadrant need to invest in building it deliberately — not assume it arrives with tenure. The work that AI cannot do doesn't develop itself. --- ## What this actually means for you The question worth sitting with isn't "will AI replace my role?" The honest version of that question is: "Am I spending my time where AI can't go?" If you're still the person doing the account health summaries, the renewal narrative drafts, the risk flag writeups — not because you want to, but because your organisation hasn't made the tooling investment — that's a different problem. It's a data and infrastructure problem and it has a business case attached to it. But if the tooling is there and you're still doing those tasks because they feel safe and familiar and measurable — that's the thing to interrogate. Safety in Replace is not security; it's exposure. The revenue-generating CS leader lives in Elevate and Protect. That's where the commercial conversations happen. That's where trust gets built and defended. That's where the business case for CS as a function gets made, or doesn't. The line is clear. The choice is yours. — Iliyana Next issue, 20 July: Reactive Customer Success Has a Price Tag. Most CS Leaders Just Don't Know What It Is. I'm going to give you the calculation. --- *CS in the AI Era is a bi-weekly newsletter for Customer Success leaders in European SaaS. If someone sent this to you and you want to receive it directly,* [*subscribe here*](https://csintheaiera.com/customer-success-is-not-broken-the-job-description-is/#/portal/signup)*. Or if you know* a *CS leader who should read it? Forward it.* ### Customer Success is not broken. The job description is. URL: https://csintheaiera.com/customer-success-is-not-broken-the-job-description-is/ Last updated: 2026-06-24T09:39:36.000Z *Why the hardest sales call I ever made was to my own colleagues — and what it tells us about the state of Customer Success.* --- A few months ago, I found myself sitting at the table with senior sales leaders at one of the largest tech companies in the world. I was not there to close a customer. I was there to convince my own colleagues that the CS product we were trying to sell was worth selling. The product bundled intelligence tooling, a dedicated, senior CSM, and a solution architect — everything a customer needed to actually achieve value from the platform. It was, on paper, exactly what CS is supposed to deliver. And yet the room was hostile as the sales leaders didn't believe in it. They didn't think customers would pay or should pay for it. And when I tried to quantify the return — the retention uplift, the expansion rate, the reduced time-to-value — they questioned every number. I have had that conversation more than once — at Cisco, at ServiceNow, in different rooms, with different slides, and the same result: polite skepticism at best, active resistance at worst. For a long time, I thought this was a sales culture problem. But I was wrong — it's a CS mandate problem. --- 💡 **Sales didn't fail to believe in CS. CS failed to build a case that revenue leaders could believe in.* Here is the pattern I have seen across almost every SaaS company: Customer Success is designed to be defended, not sold. The team is structured around relationships, health scores, and renewal rates; the language is about satisfaction and retention; the metrics are lagging and soft. And then someone puts a price tag on it and wonders why procurement pushes back. The problem is not the work CS does because that work is often exceptional. The problem is that CS was never designed to speak the language of the people who control budget — and in 2026, with AI reshaping every commercial function, that gap is becoming a crisis. When a sales leader looks at a CS product and asks "what is the ROI?" — and the CS leader responds with NPS trends and health score improvements — the conversation is already over. Not because the CS leader is wrong but because they are answering a different question than the one being asked. The CS job description was written for a post-sale relationship era: build trust, manage renewals, escalate risk, run QBRs. All of that is real work, but none of it, on its own, is a revenue argument. And now that AI has arrived, the pressure is intensifying. Boards want CS to justify its headcount. CFOs want CS to show a direct line to revenue. Sales leaders want CS to accelerate the commercial motion, not run parallel to it. The CS leaders who will survive this moment are the ones who can make that case — clearly, in revenue language, with numbers that hold up under scrutiny. That is what this newsletter is about. Not CS as a support function that needs defending, but CS as a revenue function that earns its seat at the table. In this first issue of CS in the AI Era, I want to leave you with a couple of practical items you can do right away — a framework assessment that helps you assess your CS org's commercial mandate and three AI prompts that can help you move the needle forward based on the assessment's results. --- Framework · Issue 01 The CS Mandate Audit Ten questions to assess whether your CS org has a commercial mandate — or just a relationship function dressed up in revenue language. Score each question 1–5\. 1 = not at all true. 5 = completely true. Commercial mandate CS has a defined revenue target — not just a retention target. \_\_ / 5 CS is included in the commercial strategy conversation, not just the post-sale handoff. \_\_ / 5 CS leaders can articulate the ROI of their function in the language a CFO would accept. \_\_ / 5 If the CS function disappeared tomorrow, the revenue impact would be immediate and quantifiable — and the exec team would know the number. \_\_ / 5 AI readiness My team uses AI to synthesise account risk, expansion signals, and renewal narratives — not just for task automation. \_\_ / 5 My team has documented which CS workflows AI now owns, and which require human judgment. \_\_ / 5 The CS team's use of AI has reduced time spent on low-value activity and increased time on commercial conversations. \_\_ / 5 Executive visibility CS leadership has a direct line to the CRO or CEO — not only to the COO or VP Operations. \_\_ / 5 CS presents in the board or exec team meeting with revenue-framed outcomes, not just health and satisfaction metrics. \_\_ / 5 Sales and CS share a common definition of customer success — and a shared commercial incentive. \_\_ / 5 10–25 Relationship manager CS is doing important work without a commercial mandate. The function is at risk in the next budget cycle. 26–39 Value advisor CS has some commercial muscle but the mandate is inconsistent. Revenue language is emerging but not yet the default. 40–50 Revenue leader CS has a clear commercial mandate, AI-ready workflows, and executive visibility. This is where the function needs to be. Use this with your team, your peers, or your own reflection. The questions that score lowest are the mandate gaps — and the mandate gaps are the ones that get CS cut when budgets tighten. Prompt library · Issue 01 Prompt 01 — Audit your CS mandate You are a senior CS strategy advisor. I am a \[VP / Director\] of Customer Success at a \[company size\] SaaS company in \[industry\]. My CS org has the following profile: — \[X\] CSMs, each covering \[X\] accounts — Total ARR managed: \[X\] — CSM targets include: \[e.g. GRR %, NRR %, expansion ARR quota, QBR completion rate, health score thresholds, time-to-value milestones\] — CS is currently measured on: \[e.g. churn rate, CSAT/NPS, renewal rate, product adoption metrics\] — CS is not currently measured on: \[e.g. pipeline influence, expansion revenue, revenue per CSM\] Based on this, help me audit whether my CS function has a genuine commercial mandate or is operating primarily as a relationship and retention function. Identify the three most important mandate gaps and give me a one-sentence recommendation for each. **Output:** A prioritised gap analysis with actionable recommendations. Paste directly into a leadership team agenda or use it to frame the conversation with your CRO. Prompt 02 — Write the board slide Write a single board slide that makes the case for CS as a revenue function. The audience is \[CEO / CFO / board\]. The key metrics I have available are: \[list your retention rate, NRR, expansion ARR, and time-to-value data\]. Frame the slide so that the ROI of CS is expressed in revenue terms — not satisfaction or health score terms. Include a headline, three supporting data points, and a one-line call to action. **Output:** Board-ready slide content. Copy into your next deck — edit the numbers, keep the structure. Prompt 03 — Rewrite the CS job description Here is my current CS job description: \[paste it\]. Rewrite it so it reflects a revenue-generating CS function in the AI era. The new version should: use revenue language throughout, include AI fluency as a core competency, remove or reframe any language that positions CS primarily as a support or relationship function, and signal clearly that this role is accountable for commercial outcomes. Keep the same length but change the framing entirely. **Output:** A revised job description ready to post — or to share internally to start the mandate conversation. --- **Next issue** Issue 02 is about the part of CS that AI is already replacing and the part it cannot touch. The gap between those two things is where revenue-generating CS leaders live. — Iliyana *CS in the AI Era is a bi-weekly newsletter for Customer Success leaders in European SaaS. If someone sent this to you and you want to receive it directly,* [*subscribe here*](https://csintheaiera.com/#/portal/signup)*. Or if you know* a *CS leader who should read it? Forward it.*