Retention & customer success

Dan Lee said Nooks keeps a Slack channel with every customer and regularly checks how each is doing against its goals, such as sales productivity targets, and how Nooks can help. He said the CSM is effectively working for the customer, checking things like whether reps are performing well on calls, whether call scripts are good and whether the data is correct.

“So we have a slack channel with every customer.”

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Ariel Risman said CS at Notion acts as a thought leader in helping customers define what value looks like, and it depends on the team's biggest issue at the moment. For some it is cutting time spent on administrative tasks. For others it is reducing friction between teams that didn't work well together, so they can move with the velocity AI demands. He said to identify those issues, improve them, then iterate.

“value could be just reducing friction between teams”

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After Advantive's most recent acquisition, Nerad spent a couple of months working with a senior CSM who had been at the acquired company for 15 years and knows its customers well. Together they worked through what drives those customers and what outcomes they intended when they bought the software. Nerad said the understanding of risk and retention follows from that customer understanding.

“I have a senior CSM who's part of my team who she's been with this company 15 years. She knows the customers really well.”

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London says CSMs should try to stay tied to what the customer describes as company priorities, up to board level if possible. His reasoning is that this shows how your value aligns with the customer's business, not just with the person you happen to be speaking with, who may leave or change roles.

“so you can see how your value aligns not just with the person with whom you're speaking, the customer contact who may leave or change, but their business.”

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Asked how a leader knows the team struggles with above-the-line conversations, London says the first thing that comes to mind is unhealthy customers or predicted churn. He attributes this to CS and sales teams being trained to push what they offer and to define value the way internal training told them to. In his view, that training leaves no room for customers to say how they define value on their own terms.

“the diagnosis of that, which sometimes is an autopsy after the fact, is that we just simply didn't understand value the way the customer defines value.”

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At Microsoft, Brian says customers who had not planned how they would use the product did not consume what they had committed to, which affected later commitments. He recommends a function that helps customers set a vision of the value they will create, with the vendor's product built into that plan.

“The fact that our customers didn't have a vision for how they're going to use our product and how it was going to benefit them was a problem.”

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Kellie said the company ties the customer's business outcomes through the whole relationship with checkpoints, starting in pre-sales. For existing customers, the team revisits outcomes because they shift over time and should not be assumed to be the same. She said these outcomes guide the initial scope and where the team starts with a customer. The team still does the typical things like customer satisfaction pulsing.

“So we really try to start in the pre -sales and identifying what the customer's business outcomes are.”

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Adnan says the categories should be about challenges and outcomes, not features, and should start high level without boiling the ocean. He recommends interviewing best customers, top-performing CSMs, solutions engineers, account executives and the learning team, with categories emerging from the patterns in those conversations.

“Yeah, the first step is You got to start by asking what are the top reasons customers buy our product, right?”

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At Paycor, Adnan says CSMs without a framework default to product usage, feature adoption and support cases, which he calls means rather than an end. The framework starts with outcomes such as reducing time to hire, cutting errors or improving employee retention in HCM, then works backwards to the product. He presents this as the core of the approach, which has been rolled out to 28 enterprise CSMs and expanded to 17 mid-market CSMs.

“And so the value framework forces The CSM to start with the customer's desired business outcome whether that's reducing their time to hire”

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He says the company should make sure it knows how customers will measure value each year and that customers understand and agree on that measurement. He notes that the measure changes each year, so it has to be re-agreed at the start of each year to deliver incremental value.

“Make sure you know how your customers are going to measure value each year and then growth is going to come organically from that.”

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SMART stands for specific, measurable, attainable, relevant and time-bound, and Christine introduced it to the team a few months before the episode. She says the framework lets the team define the goals that matter to a customer and then say whether they were met, which removes vagueness about whether the customer got value. She calls it a leading behavior and indicator and one of her two big priorities for 2026.

“It takes the vagueness out of did I get value from Conga's products? Well, we defined that these particular goals were really important to you and we absolutely nailed it on these three or we didn't.”

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She says her team recently ran a training session on what value looks like to the customer and how to have conversations that let them measure outcomes. The aim is to connect Conga to the customer's root business goals rather than describing it as a product that does things. She describes this as a leading behavior that she expects to lead to better retention.

“we focused on learning and talking about what does value look like to our customer and how do we have the right conversations with that customer so we can ultimately measure their outcomes.”

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She said Deltek could automate support with AI agents, but she doesn't think customers would love that. She asked where the balance is between going faster and the point at which customers simply want to talk to someone. She also mentioned that usage data can show why a customer's usage dropped.

“I don't think our customers are going to love that right?”

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He said Deltek's AI work is aimed at accelerating time to value and enhancing customer stickiness, and that the two have to be balanced. A touchless implementation that doesn't give customers what they want could create churn risk at their next renewal, because they feel disconnected from Deltek people. He said the company still needs to work out where AI should apply.

“we could develop something that is a touchless implementation that doesn't actually give the customer what they want or provide them a great experience and then there are immediately a churn risk at their next renewal”

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He said there is about a 50-point difference in net promotion between customers on the high-touch professional model and those on self-serve. He said ERP NPS typically sits between zero and plus 15, so a 50-point gap is very large. He linked the gap to customers being led, challenged and shown value realisation.

“there is about a 50 -point difference in net promotion.”

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She said some customers do not want to talk to the company, renew, and are happy as long as they get what they need, and that choice is up to them. She described the over-rotation as going in the wrong direction a little bit, mainly with the long-tail group of customers. She said the new platform is being used to re-create the engagement that had fallen by the wayside, and that it has taken a while but results are starting to show.

“we over -rotated it in the wrong direction a little bit”

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He presented customer demographics as the third factor limiting automation. He said this affects how much conversation can be contained, because some customers in airline and healthcare insurance segments simply prefer humans.

“if you're dealing with the young demographics, they're probably more open to digital channel interaction, chatbot, talking to chatbot, versus much older demographics, they will potentially will really prefer in -person interactions.”

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Kellie said the team cannot engage every customer all the time, so it uses data and digital engagement to identify when a CSM should step in. Once the blocker is removed or the next step is taken, the customer goes back to working on their own. This is how she describes the balance between digital and human engagement.

“you can use the data, the digital engagement and all the things that you're doing to then identify, hey, now it's time we should, you know, step in”

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Chael says Lawrence, who runs the long-tail digital motion, looks at data signals in the install base by customer to find where they are not adopting, where they are adopted, and where they are stalled. Early-career staff are deployed to have conversations about why and how to help. Chael says this began a couple of years ago and that AI now helps these staff get smarter faster.

“look for data signals in that install base and by customer, where are they not adopting?”

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Jordan says his nightly runs identify the accounts flagging the most issues, and that with an understanding of why customers stay or churn, some accounts are worth 10 times more than others. He says the other 90% are ones intervention will not save, while accounts that say a priority will come in six to 12 months are worth engaging.

“And so ignore this 90%. These 90%. These are the ones where actually intervention can help.”

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Eric described a churn-signal integration with Slack: if you own an account at G2, you are pinged every day when your customer is shopping on someone else, and told who they are looking at. He said account owners prioritize this in their own time, and G2 teaches customers to do the same.

“we will ping you every day. If your customer is shopping on someone else, we'll tell you who they're looking at”

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Carsten says that with thousands of customers, teams cannot simply call each customer and try to judge sentiment. He argues that risk management and detection need to come from data, using AI.

“So we, we can't just jump on a call and and and try to figure out whether with a sentiment, OK, how's the customer doing.”

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He said this worked in HubSpot's first ten years because it was transactional with thousands of customers. Each cohort mirrored the whole base for size, industry and region, so monthly scores reflected new patterns of promoters and detractors. The top detractor reasons went straight to the roadmap, and the team could see whether they moved.

“We split the customers into six cohorts, all of which were representative of the entire base”

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Karri Saarinen says that in many companies product and customer teams are isolated, and Linear has a customer feature and a customer request feature so that product teams can see customer problems, blockers and deal issues. He says a Salesforce integration lets customer requests be pulled into Linear, where anyone can view what a customer or segment is saying, and that sales and customer teams can then tell customers when a fix ships.

“we have also like a Salesforce integration now to help with this like those those nodes can be like captured from Salesforce and then like you can pull them into linear”

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He describes a user who has to change personal settings, configuration or workflow rules, and says the frustration gets logged as a request or heard by a CSM. He says it may show up in the product nine months later. He offers this as an example of how feedback travels in the old model.

“what that gets logged as a request or CSM hears it. Maybe it shows up in a product nine months later”

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Ping Wu said these conversations arise from failed processes, broken products or confusing statements. He said AI's role here is to give full observability across channels, find the root cause and fix it, and gave United Airlines as an example of doing this with Cresta.

“The first bucket are the conversation that shouldn't even be automated or augmented. They should not even exist.”

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Grant gives outreach-and-response as an example of work suited to the agent's back-and-forth. Another is a value-based message noting the renewal is coming up, pointing out a feature the customer isn't using, and linking a white paper or training module. He expects humans to do more of the late-stage negotiation, the 'pissed off' customers and odd scenarios. He says the agent can still work through more of the action inventory over time.

“And then when you get into the late stage like negotiation or the pissed off customer or the one that's got some random scenario to play out, we know that the human's going to do more of that.”

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Amanda Kahlow says her company will still have many CSMs even as it builds a digital CSM. She no longer wants CSMs writing support tickets, updating content in the superhuman's brain or handling routine tasks, and wants them thinking about what else they can do to drive value. She says customers get more value because the superhuman answers their questions, and her company is building more solutions architects.

“I just want them to be more of the solutions, the thinker, not the doer, not the task person, right?”

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Chuck Ganapathi says the human relationship remains central to customer relationships, and in Gainsight's Atlas model humans will handle judgment, oversight and strategic intervention. He says humans in the loop let the company make the system's reliability predictable and put guardrails around what the agents do, and that agents and humans train each other in a learning loop.

“the humans will drive the judgment, the oversight, the strategic intervention when things go wrong”

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Cassie Vaughn said the medium-touch motion replaces what used to be scale CS, and that the tech-touch motion uses agents. She said agents currently handle basic discovery, collecting and synthesising customer information, recommending optimisations inside the product, and building from scratch, tasks that used to take CSMs hours. She said CSMs stay for judgement, complex scenarios and the people who need to understand the value they get from agents.

“we've segmented our customer base into a high touch motion, which is where my team sits.”

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He gave this as a way to create value on the complex and high-emotion calls that stay with humans. He also listed answering knowledge questions directly for agents and drafting emails as ways to support the human agent.

“Maybe you can automate the first 20 % by handling authentication. All the after -call works by automatically doing the data entry and entry and then take away the summaries”

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He gave examples such as a flooded house or lost property on a flight, where customers want to be heard by a person. He said AI should free agents' hands so they can be more emotionally available to the customer, and that for businesses this builds loyalty.

“So for those, we believe that the role AI should play is to really augmenting the expert humans and make them really do a good job and free up their hands so that they can be more be more emotional available to the customer.”

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Ping Wu described this as the second bucket of conversations, where customers just want the task completed. He said an AI agent or a website that automates the interaction is the right solution here.

“In the second bucket of the conversations are the one that neither party want to even a human, they just want to get it done like password reset or tracking my shipment.”

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Snehal said the team was lead hungry and would build requested features within a day, which left the product and marketing pages cluttered. The drop in usage after onboarding, including for customers who had passed POC, prompted the team to analyse why engagement was declining. They concluded they had been onboarding any company that arrived without understanding how essential the product was to it.

“what we saw post two months of onboarding after POC or even as a customer, the usage would essentially start dropping.”

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He says the cause is usually a lack of structure keeping sellers disciplined on ICP customers, setting good expectations and setting up customer success properly. His example for Roadrunner's context: a rep who closes a CPQ deal without involving IT leaves CS facing an IT team that may politically try to kill the project. He said involving IT probably triples the likelihood of a high-LTV account, but reps paid only on quarterly revenue aren't incentivized to do it.

“instinctively, most people think the retention causes product deficiencies or customer onboarding deficiencies. That's the minority in my experience. It's mostly a sales issue”

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He said a great CPO or CTO told him this. He attributed to a CRO the view that a CS process alone might lift GRR two to three percent, while fixing the product could lift it 15 to 20 percent.

“When you have a GRR issue, it is a product problem. Always a product problem.”

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Dan joined the company in 2013 and eventually became a customer success leader there, running quarterly win-loss analysis on customer outcomes. Some customers were up and running within weeks and tended to grow and expand, while others still had not implemented the software six months after signing, even though the same onboarding and implementation teams worked with both groups. Dan concluded the difference lay in the customer and the personas using the software rather than in the onboarding.

“Conclusion was it wasn't really the variance in how the customer was onboarded. It was more of a variance about who the customer was.”

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Tunguz compared sales engineers to CSMs and FDEs to AI CSMs, arguing that complex technical implementations justify technical staff while simpler apps are served by a CSM. He said Snowflake famously did not use CSMs because its products were too technical. He said the ROI on NDR investment is significantly higher for a simple app with a CSM than with a sales engineer.

“And so I think it has more to do with the complexity of the software and the ROI on an NDR investment dollar.”

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Ian uses Zoom as an outside example he says he doesn't know well: it boots up and works, so CS there would be more about strategic integration than product help. Products like IT asset management, or CX and EX tools being reshaped by AI, bring frequent questions and new developments. In those cases CS also passes market insight back to sales, and he likes that sitting under the same umbrella.

“But my Zoom boots up and it works, and the most I do is work out if I'm putting a blur on or not.”

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Asked whether the revenue leader should own CS and retention as a default, Ian answered no. At Freshworks he owns net retention, and expansion is a large part of the business, so new business that churns out has no value to him; that is why CS sits under his revenue leaders. In previous single-product companies with a mostly new-business motion, CS sat outside the revenue org and he says that made sense. He calls the current setup right 'for this moment in time'.

“No is the answer to that and i think it's all about several things one is about stage commensurate”

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He said sometimes a very technical product needs a support-heavy model, while other times it needs a more consultative one. He has a head of support and CS leaders under him, and said the support roles are very important even though the leadership layer owns the number.

“I own the number of what levers do we pull to deliver gross and net and sometimes you need to be support heavy on a very technical product. Sometimes it needs to be more consultative.”

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He contrasted a tech-enabled CS model, where the team bridges gaps in the product, with AlphaSense, where the product works well once customers start using it. His team's job is to get customers to use it, change their behaviour and connect the value by telling them a story.

“I got to make sure that I change the way that you like I change your behavior and I I tell you a story I connect the value”

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Carsten describes his previous company's CS history: it started with generalist CSMs and had customer success engineers from the beginning, then added CS Ops specialists as it grew. He says SAP's complex portfolio raises the question of whether to have CSMs who orchestrate specialists or CSMs with deep product knowledge, and that for him the answer is a combination of both.

“I think depending on the product complexity and the organizational complexity, you need also those orchestrate, but for me it's a combination.”

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Speaking as a buyer who enjoys buying software, he says that as he moves from BDR to AE to renewal manager, his vendors have no idea who he is. In his view, everyone at a vendor should now know every detail that matters about the customer.

“it's like the goldfish with the 5 second memory. They just have absolutely no idea who the hell I am. That is inexcusable.”

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A customer moves from implementation to customer success and then to support, and each handoff has always had friction. He wants to use AI to remove that friction rather than let AI create friction in the background. He said these handoff points are among the first things his new role will address.

“we still have that friction”

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Carsten reports customer feedback from SAP's conference that customers value CSMs who have deep knowledge and create value directly. He contrasts this with CSMs who say they do not have the answer and schedule another call to bring in specialists.

“it's not the situation where you talk to CSMs and they say, I don't have the answer, but I have three or five specialists.”

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Usha says that when she took over customer success, customers struggled with technical issues like SSO and DMARC email setup. She first created a level-two escalation team of two or three people, but found it added friction between levels. The better fix was upskilling the level-one team to handle these issues in their normal workflow.

“the real solution was to actually upscale our level one team to be able to handle that within their own flow of work.”

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She said the roles are blending with AI, and that at some point a single person could handle onboarding, implementation, support and renewal for an ERP customer. That raised the question of how to move from three separate organizations to one coherent customer experience. She uses the term convergence for this blending.

“like you may at some point with an ERP system have the same person onboard you, implement you, support you, and maybe even do your renewal”

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Internally the role is called account manager and externally product advocate. The advocate onboards the customer and works with the field engineering organisation to keep bringing new things to build on Replit. Ghazi describes it as designed with an AI-first mindset rather than the classic CSM and renewal structure.

“And basically you, you will get assigned A Replit product advocate the moment you become a customer.”

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She said roles exist because humans have limits on time, capacity and recall, but the buyer does not change roles. HubSpot began its superhuman in qualification and closing for SMB, then found customers needed support answers, and it kept the same superhuman rather than switching. She said the superhuman picks up where earlier conversations left off, so customers don't start over.

“But our superhumans supersede across all of the roles because your buyer is the same buyer across that whole journey.”

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He said he tested the idea with teams at an event in New York. The person covers support, services consulting and technical CSM questions, so the customer is not handed off to many people. He said the specialists who previously handled these questions stop dealing with repeated problems and move up the value chain. He described this as one of the newer ideas he is testing.

“They're generalists in the concept of post sales and they can apply them across all these disciplines.”

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Josh contrasts the 'every T time' framing with the customer success focus on time to value. He says he prefers it because it requires giving customers recurring value. Roberge replies that the two are not mutually exclusive. Earlier he noted that a one-time milestone like Facebook's seven friends in a week cannot detect a customer who tries the product and then stops.

“you have to give them that recurring time to value. You have to continue.”

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Adnan says outcomes should be concrete enough to measure but broad enough to apply across the customer base. Leading metrics serve as an early warning system and coaching tool for CSMs, while lagging metrics are what gets discussed with the executive sponsor. He says this is what gives the framework teeth.

“And your leading metrics will be early warning system and coaching tool, lagging metrics, the things that you're going to talk to about with your executive sponsor.”

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Cassie says enterprise renewals take about a year, so Primary's portfolio companies look at other leading indicators. One is time to expansion, which can mean time to commercial expansion or time to use-case expansion. She says she pushes portfolio founders on this because retention cannot be read from renewals alone early on.

“it's going to take you a year to get a renewal in an enterprise environment like what are the other leading indicators that you can look to and so one of the things that we talk about is just the time to expansion”

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She said instructional designers spent time turning launches into classroom experiences, but people now learn from LinkedIn, podcasts and peers, and reps on Zoom training often do not pay attention. Justworks shifted to learning reps can consume on the go that connects to what is happening in the market.

“So we really needed to move towards like bite-sized learning.”

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Kellie said the professional services team was doing a lot of education inside onboarding, so the company pulled it out, made it higher quality, and grew what had been a very small team. She said the focus is on producing less instructor-led content and more online courses, a knowledge base paired with short how-to videos, and thought leadership; the company also does a lot of webinars. The goal is to let customers self-serve on their own time.

“to one, we wanted to separate education a little bit more, even in that initial onboarding because our PS team was technically doing a lot of that.”

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Monika Saha says most of Articulate's customer education is served through its community platform, organized into spaces for each product. Its training team produces multiple bite-size training pieces every week, along with weekly challenges, and the content is the main draw for the community. She also says Articulate uses its own product heavily for internal field enablement, including product launches and legal training.

“for us, the community is a big part of getting that content out there”

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Adnan says customers are less willing to sit through hour-long or multi-week training to get certified. He says short TikTok- and Instagram-style clips are starting to pick up, and Paycor is using AI and knowledge around key moments of truth to show in-app pop-ups that guide customers.

“I think the hard thing in today's attention economy right is being able to capture anybody's time to really go through complex training and learning.”

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Christina Parra said owning renewals shows how important value conversations and human check-ins are. The value conversations about workflows translate into how the customer thinks about the partnership, which is why CS should own commercials. She said she always knew this from one side or the other, but feels it much more owning both sides.

“I think a lot of conviction that the CS world can and should own commercials”

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Christina Parra described a first 'CS Evolution' that merged relationship managers and renewal managers with CSMs to bring the commercial piece into CS. The next evolution adds the technical piece. Her reasoning is that adoption, consumption, commercials and value are inextricably tied, so one team can be a consultative partner across all of them.

“we launched CS Evolution where we actually merged our relationship manager renewal manager motion with our CSM motion. So we brought together the commercial piece. And then this next evolution is bringing the technical piece in.”

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He said that to join a high-growth, high-velocity company you need to own an upsell and growth number. He said this matters if the company is trying to grow 40 to 70%, because someone needs to protect the flank and make sure the customer gets more value than they pay for.

“you absolutely need to own an upsell and growth number. Now, I believe that doing that in conjunction with sales, is really important actually if you're trying to grow it 40, 50, 60, 70% growth rate”

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He treats gross renewal and gross retention as the baseline number for customer success. He contrasts this with growth numbers, which he says depend more on the business.

“So I think you absolutely need to own a gross renewal rate and a gross retention rate.”

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He said he has worked 17 years in customer success leadership and that whether CS should own a number has never been a debate for him. He wants a role focused on revenue impact that owns a number and calls the forecast from the start, including what the renewal rate looks like.

“I would never take a role that doesn't have revenue focused. Impact owning a number calling your forecast from day one”

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Manish said a CSM's GRR goal comes from bottom-up numbers plus a top-down allocation of company GRR or attrition goals. Expansion within the portfolio is a second goal, and health, meaning value, usage and customer success, is a third, so CSMs look beyond the upcoming renewal. He also said a lead generation commission was added to these targets.

“So if you have a portfolio of accounts as a CSM, then you have a GRR goal based on, of course, the bottoms up as well as or top down allocation based on the company goals for GRR, or, or attrition.”

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Sangeeta says the first step is getting CSMs to think about how the business grows. Keeping CSMs and sales in separate silos creates tension, because leaders want CSMs to help with expansion while CSMs say that is not what they are paid for. She adds that the wrong incentive structure can destroy culture.

“Putting them in very different silos creates a lot of tension within the system because he wants the CSM to help with expansion activities and the CSM says, hold on, that's not what I'm paid for.”

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Seong says his team of about 35 people cannot cover thousands of enterprise customers by hand, so it relies on tooling. He lists signals to watch: a competitor showing rising usage across development teams, a drop in product usage, and loss of engagement when the champion moves teams or leaves. He describes building these detection systems and defined actions to take when signals appear.

“Hey, our usage has dropped off, or, hey, we've lost engagement because, guess what, our champion just got pushed into another team or just left the company.”

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Rob said the team partnered with the account management team on what they call an early warning system, designed to intervene when value signals are not seen early. The intent is to make sure the team talks to the customer and that the customer gets what it needs.

“we partnered with our account management team for what we call like an early warning system where we can intervene if we don't see value signals early on”

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Eric said G2 lost a six-figure deal, and when they went back and looked, the customer had been telling them nine months in advance that they were not happy. He said G2 had not been using its own tool to extract those signals.

“you actually go back and look and they were actually telling us nine months in advance that they weren't happy”

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Eric said customers do not churn 90 days before renewal, and that they can churn about three days after they buy. He said teams need to aggregate many signals, alongside product health scores, to see churn coming.

“they didn't churn like 90 days before the renewal. They churned like 3 days after they bought it”

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Signals include a customer viewing compare pages against a competitor, looking at a competitor's pricing page, and buying other products in the category that could represent future leakage. Eric said G2 uses these signals internally well in advance to get ahead of churn. He said they should be aggregated with product health scores.

“we kind of flipped the buyer intent into what I call churn intent”

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Andy said customers are still buying because they have not had a bad experience and their contracts have not run out. He said funded AI companies are hiring CMOs and CROs but not heads of CS, which makes the market harder for CS leaders. He cited the view that companies churn in year three, saying it came from Nick or someone else.

“I think a lot of these AI companies are in year two and they're about to face it.”

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Cassie says if she were a betting woman she suspects companies with weak retention will face a reckoning in year one or two, and then the good ones will get better, so cohorts should improve over time. She says it might not be next month or next year, but it is ultimately going to come. She also says the enterprise buyer may be slower to consolidate tools than she expected.

“if I were a betting woman I suspect that for companies where that happens It'll be a reckoning in year one or two and then the good companies will they'll wise up about it”

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He said 2025 was a year of testing tools in sandboxes, while 2026 will be a year when buyers hunker down and pick a few solutions. He said people should not sign multi-year contracts because a better product may come out within a year.

“we're going to see massive GRR issues for a lot of these companies because a lot of people are signing up month to month to month.”

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Monika Saha says that during her time as CMO at Gainsight, she saw how data-driven the customer success organization was. She says this depended on structuring the work around a clear goal, from organizational design through systems and processes. She says seeing this from inside Gainsight, which teaches others how to do it, shaped her approach.

“it's all the way from organizational design to the systems, to processes, and everything else.”

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He said the first thing he does at any company he joins is make sure there is a forecast built both top-down and bottoms-up, with every person calling their number. He validates it the same way a sales forecast is validated, and says this is how CS gets treated as a revenue function.

“the first thing that I always do is at any company that I join is make sure that we have a forecast that we are focusing on bottoms up top down and bottoms up that everyone is calling their number. We're validating that in the exact same way that you do a sales forecast.”

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He says sales and marketing continuously evaluate their touch points to see whether they attract the right customers and drive conversion, and he wants post-sales to take the same rigor. He says he has traditionally looked at customer health and churn and told teams what to do, but has not always tied touch points to outcomes, value and ROI.

“Are we actually correlating those touch points to the customer outcomes”

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Manish said a CSM measured only on NPS is doing only the hygiene part of the job. He argued CS becomes essential when it can articulate a straight line of sight to top-line or bottom-line results, the way sales has a line of sight to quota.

“And so CSM that measures themselves on NPS is only the hygiene part of the story.”

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Samantha McKenna uses a Sales Navigator list rather than a saved search: any stakeholder multi-threaded into a closed deal is added to a list called existing customer job hopper. Unlike the territory searches, this tracks every departure, not only moves into your territory. For extra credit, when a past buyer lands in an account owned by a peer, she tells that peer, which she says builds morale and camaraderie.

“every single time somebody closes a deal with us, any of the stakeholders, the people that we're multi -threaded into, they get saved into a list.”

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Evan gave this as his estimate, hedged with 'I think'. He cited it as evidence that customers are a major source of opportunity generation as well as product input. He said this was one reason the company planned to build a customer marketing function.

“I think 40% of our customers in our biggest quarter last quarter were former customers that just are moving to a new company and bringing us in.”

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Margo Martin said rolling out new documentation for a new version fell by 80%. She said customer training on a new version went from months to weeks, and that the 80% reduction took it to days. She described these as large time savings for Deltek's own teams.

“Taking it from months to weeks, reducing that by 80 % to days, right?”

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Adrian said a customer success manager used to look up data and build a slide deck by hand. Now an agent in Claude desktop looks up account information and call history and builds a password-protected Webflow page the customer can review. He said they can now do more of them, even monthly, because preparation, not the call, was the constraint.

“they took what took something that took normally 5 to eight hours depending and it's now 15 minutes.”

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Ghazi said he is not building customer success. Instead, a role Replit internally calls account managers, a common term among revenue leaders, goes to market as Replit customer advocates. They come on when the AE closes the deal to onboard the customer and then keep planting seeds to retain the account and drive further use cases in it.

“I'm not billing customer success here.”

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Dan says he spent ten years in customer success and in every fiber of his being does not believe it should exist as a function. He argues that as consumption-based models grow, value realisation has to happen every day, with no three-month window to implement and get it right.

“I don't believe CS should exist as a function. I think it's causing more problems than it is solving.”

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Seong says the customer success professional must combine technical depth with a point of view and the ability to prescribe solutions quickly. He notes that large companies often do not talk to each other internally, so the vendor ends up passing information between business units. He says this gives access to the broader picture of how the customer makes money.

“large companies actually don't talk to each other, right? So you end up being kind of this information broker.”

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Chael uses the tour guide analogy to describe how his team should guide customers through their identity security journey. He says customers are scared right now and want people to lead them through and tell them what is right. He contrasts this with a taxi driver who lets customers tell them what to do.

“Customers want to buy from tour guides and not taxi drivers.”

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He says he has never been a CS leader and is assuming this goal, and that CS leaders should aim to be the person their contact calls for industry news. Josh notes that Gainsight is going through change and wants its team seen as leaders and guides. Darren agrees that the team should be teachers rather than only telling customers about new features.

“I want to be the person that my contact calls and says, hey, what's happening in the space?”

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Christine says that when she talks with customers about understanding what value is, they nod and say it is the story they want to tell too. She says customers sometimes do not know this is what they need to ask for, so the CS team has to be able to advise and lead them to it.

“Sometimes customers just don't even know that that's what they need to be asking for help to do. And so we have to be able to advise and lead them there.”

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He responded to a question about whether gaining more wallet share is underappreciated as the market gets harder for new customer acquisition. He says companies that bought point solutions and stitched them together often found themselves no further forward after a lot of work and money.

“I think wallet shares like the byproduct of helping them solve their business problems.”

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Adnan says that by understanding where the customer is and where they want to go, Paycor can plug in a product that addresses the need. He says this has produced expansion and NRR results, which he describes as a huge success, and has made CSMs more strategic.

“And so now you have some white space and you talk about product purchasing additional products and expansion and things like that.”

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He describes customers asking the company to solve additional problems once it has helped them achieve their goals, which makes the company a trusted advisor. He says those customers then come back and buy more, which is the source of growth in his view.

“when you drive customer value, like growth just comes, right?”

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Asked whether the role is becoming purely technical, Christina Parra said 'definitely not'. Getting customer commitment to a multiplayer agentic workflow through a workflow diagram requires deep discovery: understanding the customer's business, tech stack, what they care about and what value they need to see. She called these core CS skills.

“You have to have deep discovery skills. You have to understand their business and their tech stack and what they care about”

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Seong describes a give-and-take where the team keeps uncovering more pain while also showing additional areas where it can add value. He says the aim is to find well-validated, quantified metrics in hard dollars that can be captured as evidence of value. He presents this balance as the trick of the post-sale role.

“let's uncover more pain, but also let's uncover where we can find some really well-validated, quantified metrics in hard dollars”

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She said that because the activity is labelled discovery, some junior CSMs associate it with sales and do not realise that discovery is the core of their role. She argued that the quality of insight from recorded calls depends on the questions asked, so asking good questions is a core skill.

“you don't really realize that like the entire job of a CSM is doing discovery”

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He said he thinks coverage ratios are going to expand naturally, if companies empower CSMs with the right tooling. He said the jack-of-all-trades expectation is going to rise by a factor of two or three. He said the same expectation applies to CS ops.

“I think coverage ratios are going to expand”

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Simon said Bloomreach does not have a traditional long tail, and its smallest customers are really important and are not customers paying $2,000 a year. The efficiency approach isn't just about building a digital-only tier but about making CSMs more effective and valuable across more accounts, with agentic AI extending the team to smaller customers.

“it isn't about just building a digital only tier, it's about making sure that CSMs can be more effective and more valuable across more accounts.”

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Diane Wu says CS leaders traditionally plan coverage with a tiered model: enterprise high-touch CSMs, mid-tier, and digital. She says a high-touch CSM has typically covered about 10 accounts, or about 20 in a highly productive model. She expects AI, and later agents, to change how many accounts a human can cover.

“you have your sort of enterprise level high touch CSM at a one to 10 or maybe 1 to 20 if you're a highly productive model.”

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Manish said productivity gains come from reducing friction with AI and automation, and from giving CSMs simple use cases such as QBRs and dashboards so they can focus on what matters. He framed taking a CSM from 10 to 15 accounts as the aim, creating more coverage rather than adding headcount.

“How do you have CSM that covers 10 accounts, cover 15 accounts, right.”

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Josh Schachter says Gainsight's pitch is that customers sign and Gainsight owns their end-to-end renewal, running the renewal playbook through Gainsight with AI and humans in the loop. For the long tail it promises to take GRR from X to Y, which he calls low-hanging fruit because unassigned accounts can be given 'AI human in a loop' coverage. It will not sell on calls made or plays run, but on outcomes like 'we renewed this guy.'

“You sign on the dotted line, we are owning your end -to -end renewal.”

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Grant says the long tail is where companies feel the most pain, because it is hard to scale cost and engagement for many smaller customers while also retaining the large accounts that drive most ARR. At ServiceSource they started with the long tail. Once they proved value, they quickly found other ways to increase coverage for the client. He says the 2026 conversation is the same as the one in 2006.

“here we are in 2026, and I swear it's the exact same conversation from 2006.”

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Chuck Ganapathi says that as new logo acquisition gets harder, companies must go back to their base and sell more, and small customers are a growth engine and can be a great source of pipeline. Host Josh Schachter adds AI-native companies as an example: they may be small in raw volume today, but their growth rates suggest they will become premier accounts.

“your long tail may actually be a great source of pipeline”

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Chuck Ganapathi says the usual pattern is that about 20 percent of customers drive 80 percent of revenue, and the best people focus on that high-touch group. He says the long tail is human-heavy and uneconomical to serve with people because contracts are small and renewals are numerous, so most companies ignore it and accept 60 or 70 percent churn, which he calls a huge waste.

“So what most people do is ignore the long tail and then accept a 60 or 70 % turn.”

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Chael says reps at the lower end of the market may have hundreds or thousands of buyers in their territory and do not receive much support from software companies. He attributes this to churn at that level not being as painful for the company. He presents Okta's digital long-tail motion as a response to that gap.

“because the churn at that level isn't as painful for a company”

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Amanda Moran described the digital program as foundational for all customers, with some parts targeted at particular segments. The community is meant to matter most for smaller customers who get less one-to-one engagement. She said the team is still being built and will expand as needed.

“there are about five people who are dedicated to driving the digital programs.”

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Samantha Murray says a digital motion regardless of delivery channel should be the underlying layer, with the human CSM motion layered on top. She says companies get the same intent signals post-sale as they do pre-sale, but have not traditionally tracked them well. With that visibility, teams can spot expansion opportunities and churn risk, such as a customer disengaging from the academy or community.

“really truly thinking about a digital motion as the underlying layer that the human sort of CSM motion gets layered on top of”

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She said that the bulk of Supermetrics customers are in its self-service business and that the team wants to carry the digital backbone it has through to enterprise segments. She said this lets human-led engagements add more value.

“how do we make sure that that digital backbone that we have, if you will, is a journey we're carrying through even to the enterprise segments”

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Christine says the industry defined digital or tech touch motions as long-tail-only and that this needed to shift. At Conga she is working to apply digital motions across the entire customer base, including enterprise and strategic accounts. She frames the goal as the same for every customer: that they use the product and maximize how they use it.

“we're only going to use this for customers in the long tail. And I think that is something that needed to shift.”

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Brian contrasts this with consulting, where a firm delivers a strategy and sends an invoice. At Microsoft, success meant customers were actually running workloads in Azure that they would keep running because they were valuable, so the strategy had to produce that result.

“We were measured on, are they actually running workloads in Azure that they're going to keep running because it's valuable for them?”

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Rob said CSMs have targets for their book of business, aiming to advance a certain percentage of customers from one stage to the next in a given quarter. He said this gives a clear mandate for measuring progress. He contrasted it with counting whether a QBR happened or how often the customer was talked to, and said the measure is actual adoption metrics.

“So our CSMS actually have targets for their book of business to say on a given quarter, I want, I want to see them advance their book of business a certain number of percent of customers from one stage to the next.”

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Pradeep says Microsoft defines its top-level customer success KPI as what percentage of customers who have committed to move to Azure or deploy a project are completed or deployed on time with full value. He says this metric is tracked weekly, monthly, by country, by workload and by every other slice. He calls it the key metric the business is run on.

“That is the job. One metric is a what is the commit to consume percentage for this week, this month, by country, by workload, by by all of the slices.”

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Another board-level question London uses asks whether the customer has gotten an email from finance, the day before a board meeting, asking for a bullet point for a slide. He says customers recognize the situation strongly, which lets you ask what their bullet point would be about. He stresses that the scene must be the customer's scene, not one that leads toward the vendor, such as asking when they'd love to use a new feature.

“have you ever gotten an email from finance saying they need a bullet point for a slide for the board pre the next board meeting”

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London says all his questions include a word that signals to the customer that the question is about their world. Board meetings happen in the customer's world. Competitor outreach does too: customers often start their answer with 'just happened yesterday', because they get calls, sit on email lists and attend webinars. He says this approach 'breaks open' a lot of insight.

“All the questions have a word in them that trigger something in the customer's brain that says, that question's about my world, not the vendor's world”

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Josh Schachter says the board question works because it puts customers in the room mentally rather than asking a generic priorities question. He adds that it raises their status: a director feels that the vendor thinks they have insight into what the board is discussing. London agrees and says it isn't manipulative, because the intent is to see the customer as a whole person.

“You're not just saying, what are the top priorities of the company right now?”

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London anticipates the objection that many customer contacts don't sit in on board meetings. He says it doesn't matter, because the question asks for their view of what's being discussed. In his experience they generally give a relevant, insightful answer that can then be brought down to their own area.

“I know there are people listening who will say, my customer doesn't sit in on the board meeting. It doesn't matter. You're asking them what they think I would hear if I snuck in.”

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London's sequence is simple: the board-level priority, then 'what's difficult about your job in achieving that, what's in the way for you?', then 'how do we fit into your equation?'. To make it personal, he also suggests asking how the company-level priority has changed what the customer needs to deliver in the next six months.

“And then the next Question would be, what's difficult about your job in achieving that? Like, what's in the way for you? And then how do we fit into your equation? 1, 2, 3.”

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London's opening question asks what topic would dominate the customer's next or last board or executive leadership meeting: a priority, challenge, mission or goal. He says it does two things. It disarms customers because they aren't being walked through adoption stats, and it sets you apart from other CSMs, sellers and vendors. The answer becomes 'the first dot' to connect to the value the customer needs you to deliver.

“If I could sneak into your next board meeting or your last board meeting or executive leadership meeting, what do you think would be the big topic of conversation that's being discussed?”

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Adnan credits Bob London's UBR method, which he says trained the team on pointed and disruptive discovery questions. The board question asks the customer to imagine stepping into a board meeting and name the one thing being discussed. He presents it as a question the team still uses.

“I think the team really likes asking about, you know, what their board is talking about.”

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Kellie Woodin said Notion is not a point solution, so her book spans many industries, setups and workflows. Because she has so many customers, she can usually point a customer to a similar industry, size or setup she has worked with. Ariel Risman added that customers often want to learn from an adjacent vertical. His example was a facilities team learning from how a construction management firm uses agents to manage physical assets.

“they want to learn what maybe not someone in financial services is doing, but what's the construction management firm doing?”

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Christina Meng said champions in the network rarely ask product how-to questions. Instead, they want to hear from peers and help each other, and she said everyone is learning together because AI is new and few people in organizations lead these efforts.

“The number one question is I just want to hear from other people how they're doing it and they're helping each other”

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Christina Meng said she kicks off roundtables with a couple of questions and picks topics from insights she hears from champions. She brings in OpenAI colleagues, such as a CSM on measuring value, but keeps their content to roughly half the conversation because the peer discussion is where the value comes from.

“I try to keep the content to Max like half of the, the conversation because there's just so much discussion that happens.”

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Christine says a user supporting one of Conga's largest customers still wants to know the roadmap and how peers are solving similar problems. She uses this to argue that community resources should not be limited to long-tail customers. She says this is part of why she enjoys leading the community team.

“Like a user who is supporting some of our largest customers also wants to know what are the new things that are happening in our road map?”

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The plans keep the usual success-plan elements: business objectives, pain points and success metrics. They add a walkthrough of the AI maturity model to diagnose where the customer is and where they want to go. That feeds a mutual action plan listing the workflows to build together, plus recommended workflows based on the customer's objectives. The speaker said the growing library of best-in-class customer workflows lets the team be prescriptive, which customers are asking for. Some customers still get them labelled as success plans.

“We diagnose where they are and we have a conversation about like where do you want to go and how can we help you get there. And so then we pull together a mutual action plan.”

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He said that many success plans are built to get the deal closed, but the better ones focus on the post-sale work of helping the customer start using the product and eventually buy more. He framed success plans as part of the buyer's narrative, because buyers often purchase software only once and need to understand how to make it work.

“the better ones are action plans of like, how do we help the customer after that?”

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Mark Vovsi said the AI reviews conversational data, support cases and risk signals to draft plans with tight objectives and milestones, rather than bullet points. Plans load directly into the CSP, and for large customers with many products, each product gets its own adoption and risk focus. He said the goal is to create objectives people would not otherwise have thought of, and that it saves hours.

“we want to automatically load success plans for every single customer if they don't have one, or based on certain criteria, every quarter refresh it.”

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He contrasted this with the motherhood-and-apple-pie success plans and support ticket chasing he sees at other vendors. He gave the example of telling a customer they are not using a significant component of their entitlement and what peers are doing with it. He added that the message has to be contextual and feel personalised.

“something that challenges the customer that says, hey, we can see that you're not using a significant component of your subscription.”

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London's renewal-stage alternative: 'If you got a call or outreach from one of our competitors tomorrow, on a scale of 1 to 10, how would you react?' A 1 means ignoring or deleting it; a 10 means making a point of getting back to them for any reason. The customer only has to give a number, and you don't name a specific competitor. London says he came up with the question by accident and that numerous CS leaders have told him it is the best risk predictor they have. He also says the answers have more to do with candor than with competition.

“Let's just say you got a call or an outreach from one of our competitors tomorrow, on A scale of 1 to 10, how would you react? A 1 is you would ignore it, delete the message.”

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Adnan says the competitor question helped the team get past their fear of asking about renewal. He ties it to the team's shift toward having more direct renewal conversations. He presents it as one of the disruptive questions from the UBR training.

“If a competitor called you right now, you know, would you answer and what would you say?”

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The speaker said workflows are anchored to the business outcome agreed from the start with the solutions partners. Their example: if a customer's goal for the next three quarters is releasing five new products, the outcomes architect sets up workflows that improve collaboration between engineering and GTM so they ship faster. Because the work is tied to that objective, value follows without a separate re-justification.

“There isn't like a re -justification because we're really tied and anchored to that business objective.”

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He recounted that when he joined Unit4 over three years earlier, customers said they had not seen an update, had not spoken to anyone and only heard from the vendor around renewal. He said this is how you create churn rather than manage churn risk.

“This is not how you build churn risk management. This is how you create churn.”

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Chael says that when value is tied to the customer and reinforced continuously by the technical account and customer success teams, there is no need to talk about procurement three months before renewal. He says a renewal conversation like that becomes a price negotiation, whereas Okta has support inside the customer that is not only contractual. He says the customer continues because the value is evident.

“what you're not doing is selling and then talking to them three months before renewal”

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Adnan describes CS teams stuck in a reactive cycle of monitoring health scores, chasing red accounts and running QBRs that feel like product demos. In his account, customers renew out of momentum rather than a clear understanding of value. He says the value framework gives CS teams a structured way to tie each customer interaction to measurable business outcomes.

“Customers can't really articulate the value they're getting, right?”

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Carsten describes how his previous company, once it had more customers, moved from one pool of generalist CSMs to team leads and specialist roles. He says customer success engineers were there from the beginning, and CS Ops was added later, which helped develop and mature the organisation.

“So not everyone can be a CSM. Not everyone can be the generalist.”

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Richmond described a CSM at a small company doing an annual business review, then a deep technical troubleshooting call, then an onboarding conversation, because people are still proving themselves in the market. He said that as Smartling moved to an enterprise localization play, that model had to give way to specialized roles.

“you got to be willing to do everything right.”

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Richmond said he does not want CSMs to be generalists and wants them to be excellent at what directly affects core metrics. Smartling's model has an onboarding team focused on getting customers to value quickly, a tech team that knows the platform and resolves issues, and a value team focused on commercials, renewals and economic buyers.

“the only real way to get operational leverage is is to specialize those roles.”

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She said that for individual CSMs the main factor is on-time renewals, and that this means being ahead of the customer. She gave examples such as checking the customer's leave and procurement timing, for instance whether procurement takes three weeks off at year end, and asking what could go wrong.

“it's honestly coming down to on time renewals and this is when you need to be ahead of your customers”

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He says that because of the IT freeze the team usually has about 8 working weeks, so onboarding or a major milestone should be completed before the end of November. Where renewals or expansions are at stake, the team should work closely with sales to close them. He calls this old school and straightforward, but says it helps people focus.

“let's be more focused on what we need to achieve and think that we have instead of 12 weeks, we have 8-9 to 10 weeks and let's plan accordingly.”

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Adnan says the conversations have moved up a level and now function as business reviews covering strategic items. He describes customers as feeling the relationship has evolved into a more strategic one. He gives no numbers for executive attendance.

“And their conversations of up level, they're getting the executives to attend the meeting, right?”

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Adnan says the team usually refers to these meetings as joint success plans and stresses the word joint. He contrasts them with QBRs that felt more like product demos. He says the meetings are now strategic rather than tactical status calls.

“We usually mention we talk about joint success plans.”

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Carsten advises CSMs to change perspective when booking meetings such as QBRs. He points out that the customer is not hearing from just one CSM, so the request needs to justify the customer's time.

“So the customer you're talking to, you're not the only CSM, right?”

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Carsten says that when he is asked what makes a great QBR, his answer is to consider whether the customer feels the time was well spent. He says that feeling is what leads customers to agree to another meeting.

“if the customer gets out of it and thinks, OK, that was so I invested my time and that was value me, that is when they will agree to have another meeting.”

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Collins said data is a starting point, and teams need standardized KPIs with triggers that define what good looks like for each KPI. The triggers should bring issues to the CSM so they do not slip through the cracks. The playbook then sets out what to actually do about the issue.

“data is a starting point, but then you have to develop standardized ways of KPIs with triggers.”

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He said teams should not pat themselves on the back for reporting on an artifact and then go home. He said every individual contributor should look at the model and think about their business through all of its lenses, which is how the team is actually run day to day.

“So the key behind this is it cannot be busy work. It has to be actionable.”

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