Feb 1, 2024 · 1h 11m · in-depth
A customer success masterclass | How to build and scale a CS org | Stephanie Berner (LinkedIn)
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In this masterclass, Stephanie Berner, Global Head of Customer Success for LinkedIn Sales Solutions, shares comprehensive, tactical frameworks for building and scaling a customer success organization from early-stage startup hiring to enterprise maturity.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Brett holds 13.1% of the talking time here. How this is scored →
Brett as informed peer 2.5 Guest teaching 5.5 Guest disagreement 0.1 Brett pushing back 0.1
speaking balance: gold is Brett, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 21:55 Stephanie reframes early process priorities
Stephanie gently pushes back against the premise of prioritizing broad systems building early, stressing that only support intake and onboarding need rigid codification initially.
Hardest push from Brett ▶ 32:15 Brett probes CS alignment with ProductBrett challenges conventional reporting structures by questioning why CS rarely reports to the Chief Product Officer despite strong roadmap dependencies.
Biggest teaching moment ▶ 39:27 Stephanie's tactic for customer churn retrospectivesStephanie provides a masterclass on how to get brutally honest feedback from churning customers by walking in prepared with a checklist of the company's known missteps.
Brett holds their own ▶ 32:15 Brett questions standard CS org placementBrett demonstrates deep organizational design insight by asking why CS is separated from Product leadership despite being the primary channel for feedback loops.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Brett as informed peer | Guest teaching | Guest disagreement | Brett pushing back | Why |
|---|---|---|---|---|---|---|
| Trigger Points and Qualities for First CS Hires | 2 | 5 | 0 | 0 | Brett sets up a hypothetical scenario of an early-stage startup formalizing CS. Stephanie provides a structured breakdown of timing triggers, essential early skills, and hiring sequencing. | |
| Hiring Sequencing: Individual Contributors Versus Managers First | 3 | 5 | 0 | 1 | Brett probes whether to start with ICs or managers and what sequencing to use relative to sales. Stephanie explains why ICs should almost always come first and details early interview loop setup. | |
| Evaluating Candidates with the Morning Crisis Scenario | 2 | 6 | 0 | 0 | Brett asks how to extract candidate behavior in interviews. Stephanie walks through her morning crisis scenario to evaluate composure, cross-functional escalation, and systematic triage. | |
| The Lottery Scenario: System Versus Subsystem Thinking | 2 | 6 | 0 | 0 | Stephanie presents her lottery scenario interview question used for management candidates, explaining how it distinguishes subsystem thinkers from system-level thinkers. | |
| Core Failure Modes in Early Customer Success Hires | 2 | 5 | 0 | 0 | Brett asks about common failure modes of early CSM hires. Stephanie categorizes failures into lack of customer empathy, inability to balance customer vs company needs, and defensiveness to feedback. | |
| Unconventional Backgrounds of High-Performing CSMs | 2 | 5 | 0 | 0 | Brett asks about unconventional profiles of top CSMs. Stephanie shares concrete case studies of an actor, a nonprofit fundraiser, and a tech-curious IC who thrived. | |
| Balancing Firefighting, Systems Building, and Core Processes | 3 | 6 | 1 | 1 | Brett asks whether early CSMs need systems-building aptitude versus pure firefighting. Stephanie reframes the priority, explaining that systems matter later, but support intake and onboarding must be codified early. | |
| Structuring the V1 Onboarding and Value Playbook | 3 | 6 | 0 | 0 | Stephanie details the 10-step V1 onboarding process and highlights early health metrics, emphasizing deployed seat usage over vanity CSAT scores. | |
| Renewals Ownership: Dividing Lines Between CS and Sales | 3 | 6 | 0 | 0 | Brett asks about the division of renewals between CS and sales. Stephanie explains her framework based on transaction complexity and expansion potential. | |
| Customer Success Reporting Structures Across the Organization | 4 | 6 | 0 | 1 | Brett asks why CS rarely reports to product leaders despite tight roadmap ties. Stephanie explains why CS belongs in go-to-market alongside revenue and marketing rather than in product. | |
| Root-Cause Diagnosis of Churn and Account Health | 2 | 5 | 0 | 0 | Brett asks how to differentiate CS execution issues from core product flaws when churn happens. Stephanie outlines a methodical framework bucketing churn reasons into controllable vs non-controllable factors. | |
| Conducting Honest Customer Churn Retrospectives | 2 | 6 | 0 | 0 | Brett asks how to conduct post-churn retrospectives and get honest feedback. Stephanie shares her tactic of presenting known issues upfront to disarm customers and build trust. | |
| Establishing Collaboration Rhythms Between CS and Product | 2 | 5 | 0 | 0 | Stephanie describes the weekly cadence for synchronizing CS and product teams to keep feedback loops tight without over-engineering bureaucracy. | |
| Cultural Rituals: Customer Centricity and Cross-Functional Visibility | 2 | 5 | 0 | 0 | Stephanie shares operational rituals that reinforce customer empathy across company leadership and ensure customer delivery teams receive internal recognition. | |
| Capacity Planning, Staffing Ratios, and Segmentation Models | 2 | 6 | 0 | 0 | Stephanie breaks down specific account-to-CSM ratios across enterprise, mid-market, and SMB segments, explaining how capacity planning evolves with math and qualitative checks. | |
| Designing Compensation Structures and Aligning CS Incentives | 2 | 5 | 0 | 0 | Stephanie explains compensation philosophy for CS, cautioning against heavy commission quotas that distort CSM behavior away from adoption toward aggressive sales tactics. | |
| Structuring CS for Infrastructure and Consumption Business Models | 3 | 5 | 0 | 0 | Brett asks about differences between per-seat and consumption-based CS models. Stephanie highlights that consumption models require a tight focus on rapid feature adoption and enablement. | |
| Managing B2B2C Dynamics and End-User Adoption Strategies | 3 | 5 | 0 | 0 | Stephanie explains the B2B2C nature of SaaS where CS must support both enterprise buyers and end consumers with distinct enablement materials. | |
| Evaluating Value Accrual: End Users Versus Enterprise Buyers | 3 | 5 | 1 | 0 | Brett asks if CS should package end-user value for executive buyers. Stephanie explains that strategy depends on whether value accrues at the buyer or user level, citing Medallia. | |
| Four Scaling Pillars and Common Pitfalls in Customer Success | 2 | 6 | 0 | 0 | Stephanie outlines four core scaling pillars (onboarding, product adoption, data hygiene, and team support) and reflects on key mentors who shaped her leadership approach. |
Statements from this episode (32)
Berner: Formalize CS when problem-solving consumes over half of staff's day
“When you have a meaningful volume of customers, you end up Spending, say, more than half your day just resolving problems or getting them going in your product, then that's the time that it makes sense to consolidate that work into a couple of individuals.”
Berner: Early CS hires must communicate exceptionally to drive product feedback loops
“The second thing you need in those early days is you need people who communicate exceptionally well because they're the ones who are going to be your feedback loop to product, engineering, and even leadership to help you understand what is it that you need to …”
Berner: Startups Should Hire IC Customer Success Managers Before Managers
“I am biased toward hiring ICs first. Ideally, you can find somebody who either has been a manager before, or has aspirations to be a manager, or, you know, if you can assess for leadership qualities in your early interview processes, somebody who has the poten…”
Berner: Early CSM interview loops should include founders, product heads, and GTM leaders
“I think you need at least one of the founders on the loop. I think you need the head of product and or the head of engineering, and you need somebody from a go-to-market function. And I'm assuming that all of these are filled. I bias in the early days, if we'r…”
Berner: Early customer-facing odd jobs reliably signal customer empathy and fit
“And if people continue to opt in to odd jobs or part-time jobs or even career modes that Include a customer oriented experience. Then that tells me that they are a customer oriented person. I've hired people who've never done anything customer facing into cust…”
Berner: CSMs fail when unable to balance customer pain with business interests
“The second is People who have a hard time balancing customer interest with business interest, who get really bogged down in the volume or the pain that's coming in from customers. And one of the big roles that the customer facing teams play is funneling all th…”
Berner: The Jobs-to-Be-Done framework applies equally to customer success
“Oftentimes we talk about jobs to be done in the world of product, but it's very similar in the world of Customer delivery and all the teams in the customer success organization, because there are jobs that we need to build teams to deliver.”
Berner: Customer empathy and commercial mindsets are rarely found together in CSMs
“A very strong commercial mindset, which is hard to find in people who also have some of these other skills around customer curiosity, deep Customer empathy, bias for action, where people who like to help customers build their programs alongside our software, s…”
Berner: Hire a firefighter first in CS, add systems builders by fourth
“The first hire does need to be that firefighter bias for action. I think by about your third or fourth, you need to make sure you have that skill set somewhere in your team.”
Berner: Failing to codify onboarding early obscures what creates customer value
“The second place where you need to start to build some processes with implementation and onboarding. And this is actually a mistake that I see companies make. Is that they don't codify the 10, 15 step process of getting a customer onboarded. If you don't have …”
Berner: Support and implementation are the first CS roles to specialize
“As you start to scale up, you need to think about role specialization. Those are the two places where it makes sense to start specializing your roles, support or implementation, because those are the things that are very high volume and highly repeatable.”
Berner: Product usage is the essential early-stage customer health metric
“The number one most important metric is some measure of customer health. That can be a really complex answer in a late stage business, but in the beginning, it's about product usage. And product usage alone is never sufficient. But it is an, a critically impor…”
Berner: NPS and CSAT are easily gamed and less actionable early on
“In later stages, you can start to look at other metrics like NPS, CSAT, time to launch, and your implementation. Those can be great metrics. Those sometimes can be, you know, easily gamed, so they don't necessarily provide the right insight for leadership or e…”
Berner: Simple renewals belong in CS, expansion renewals belong in Sales
“If renewals are primarily just that, a renewal conversation, where there's a quick, you know, exchange of papers, a quick conversation, if there's a change in price, but there isn't a detailed negotiation or any complexity with that transaction, that renewal p…”
Berner: CS ownership of renewals and leading indicators aligns incentives
“And so if you have accountability for all the leading indicators, things like adoption, customer satisfaction, and accountability for the outcome, which is renewal, then that creates the right combination of incentives for the entire team to be doing the right…”
Berner: CS Reporting Directly to CEO Keeps Leadership Close to Customer Experience
“I am a big fan of, say, the CS organization reporting right into the CEO, because in those cases, the CEO is really close to the customer experience, no matter what phase the business is in, super early or operating at scale.”
Berner: CS Reporting to Product Creates Unnatural Organizational Alignment
“From my perspective, I think that's challenging because customer success is core to the go-to-market motion and aligning CS at minimum to the revenue team and putting it in line with marketing creates a flywheel for your go-to-market team in a way that I think…”
Berner: Nice-to-have software demands different CS journeys than must-have platforms
“If you know that you're a nice-to-have, then that upfront long-term value conversation and those relationships are critical because that is what is going to keep you in play with that business. Versus if you are a must-have platform solution, it's actually a l…”
Berner: Leading with known customer pain points elicits more honest churn feedback
“Rather than saying open-ended, why did you churn? Or why did you not renew? You can say, here are all the things you've told us. What am I missing? And, ok, if I were in your shoes, these are all the things that I was experiencing as a customer. This is the co…”
Berner: Scaling past a dozen CSMs creates product coordination bottlenecks
“As the team grows, you sort of end up with sort of a coordination problem where not every product manager can speak with every CS rep, especially when you know, you have a dozen, maybe 15, you know, reps on the CS side and only a handful of product managers. A…”
Berner: Aaron Levie required every Box business decision to justify its customer impact
“Like an example of this is Aaron Levy at Box. So from the very, very early days, he talked about customers using Box on a weekly basis. Every time the business was making a decision he asked any executive or any IC or any manager, what's in it for the customer…”
Berner: Support and implementation staffing is a straightforward capacity math problem
“So for support, real technical support, which is break-fix, managing high volume tickets or, you know, inquiries and implementations, which is basically repeatable processes, it's a lot easier to figure out how many people you need. That is like, honestly, it'…”
Berner: Baseline CSM ratios range from 5-10 strategic accounts to 80-120 SMBs
“My rule of thumb, like my starting point for thinking about ratios, is in your most strategic accounts, which are usually more than 500 K, you don't want to load up a person more than between five and 10 accounts. For enterprise, it's somewhere around 20 to 25…”
Berner: Tying CS comp to renewal quotas neglects product adoption
“The thing that I think companies get tripped up by is when you put a significant amount of comp against a renewals or expansion quota, that is going to drive behavior. And if you want your teams only focused on getting the renewal across the line, that is wher…”
Berner: Snowflake ships its customer success motion to the sales team
“Sometimes even in those cases, you don't really need a lot from a CSM, like a success motion, and sometimes that success motion gets, gets shipped over to the sales team. Sometimes I've seen that happen, and sometimes that works, like that's how Snowflake does…”
Berner: Consumption models align product adoption better than seat SaaS
“And so I do think that consumption-based businesses are a lot closer to solving that problem because everybody is incentivized on owning and really understanding that adoption path and solving for that up front rather than as an afterthought, which is what I s…”
Berner: Enterprises prefer internal end-user training while smaller companies expect vendor support
“I find that, you know, when we're selling to enterprises, they want to take care of that themselves. They want to write the copy. They want to do the email campaigns. They want to actually run the trainings, but in smaller companies, they actually expect us to…”
Berner: CS must quantify end-user value when product impact accrues to consumers
“If the value is accruing to the end user that is about maybe a better user experience or a better buying experience, then I do think it's important to try and quantify what is the value that your end consumer is getting and how is that different before and aft…”
Berner: Customer value seeds are created in the first 30–60 days
“Most of the value is created, or at least the seeds of value are created in the first 30 to 60 days. Now, if you have an implementation that takes much longer than that, that's understandable, but it's the beginning. It's the implementation and onboarding beca…”
Berner: Many $100M+ companies lack operationalized onboarding functions
“You would be amazed at how many big organizations, like over a hundred million in revenue, That don't have an operationalized onboarding or implementation function.”
Berner: Dedicated implementation specialists outperform generalist CSMs on onboarding
“The problem with that is CSM Brett does an implementation and onboarding process once, maybe twice a year. Because that's how many net new customers you get in your portfolio. Versus if you have a group of implementation specialists, they do it all day, every …”
Berner: CS leaders will not advance without strong data proficiency
“You have to be good at data. Even if you don't like it, you will not progress in your career unless you can go, go deep on the data, understand what metrics matter to your business and how to move those metrics and how to talk to the rest of the organization a…”