Most customer success enablement programs are built around a flawed assumption. Hire good people, run them through onboarding, hand them a playbook and a platform login and track activity metrics until something improves.
It's a training-department model applied to a strategic function, and to be blunt, that gap explains why enablement so rarely delivers. In fact, 69.5% of teams have no formal enablement function at all.
The customer success (CS) leaders building consistently high-performing teams treat it differently. Not as a one-time event, but as a layered operating model that spans what their people know, how their processes scale, and whether the organization itself believes in what CS is doing.
Three practitioners bring distinct angles to this question:
- At Customer Success Summit Denver 2025, Charlene Styers, Senior Director of Customer Success at BigID, focused on the competencies CSMs need to connect product capability to customer value.
- At Customer Success Festival New York 2023, Christina Parra, Senior Manager of Customer Success at LinkedIn, recalled how she built a repeatable framework for operationalizing success plans at scale.
- At Customer Success Summit New York 2025, Ishana Gupta, Senior Customer Success Director at Darktrace, stood up an entire CS function across three distinct company growth stages – with training design, organizational trust, and stakeholder alignment at the center of each.
Together, they map out three layers of enablement that most organizations treat in isolation, and which only work when they function together.
What CSMs actually need to drive customer value
When a CS team underperforms, the instinct is to reach for technical depth. More product training. A higher hiring bar. Charlene Styers spent the last year and a half navigating exactly this pressure at BigID, caught between an executive team pushing for more technical CSM profiles and her own read of where the real gap lay.
“I found myself at a tension point with my leadership, who were over-rotating on themes they were seeing in customers and saying, ‘Oh my gosh, we need to hire an entirely technical CSM team.’"
Her pushback was deliberate because the issue at hand wasn't her team’s product knowledge; after all, CSMs can’t not have product knowledge. The real problem was use-case expertise:
"You can have somebody know a product all day long and know it inside and out, but if you don't have a team of people that can tie it back to use case and develop use-case expertise, there's no bridge for the customer."
Her framework separates three distinct competencies that often get conflated: product knowledge, use-case expertise and value proposition fluency.
Product knowledge is the baseline – understanding features, functions and limitations well enough to triage conversations, anticipate implementation challenges, and speak credibly about what the product can and can’t do.
It also means being able to bridge technical and non-technical stakeholders in the same room:
"You need to help translate the gap, because often you'll have a combination of technical experts in the room alongside business stakeholders who don't know how to talk to one another."
Use-case expertise is the layer above that. It requires understanding the specific problem the customer bought the product to solve, how acute that pain is and exactly how the product maps to relief. Without it, even technically fluent CSMs end up reciting capabilities that just don't register.
Value proposition fluency is where most enablement programs stop short. Charlene identifies five categories of value a product can deliver:
- Knowledge
- Productivity
- De-risking
- Revenue
- Data
Each carries its own measurement logic. For productivity: how many hours were saved, which manual workflows were replaced? For de-risking: how much exposure was avoided? "Value can't be vague," she reminds us. "Value can mean a lot of things for our customers."
Grace Gupta
Now, the harder challenge is that customers often can't answer these questions themselves. In those cases, Charlene encouraged her team to build hypothetical models rather than abandon the conversation. She described working with one of the largest banks in the US, where the customer contact had no clue how her business leaders measured value.
Rising to the challenge, Charlene offered to “paint some hypotheticals for [them]." Her team backed into it using industry averages – average breach costs in financial services, typical data storage waste – and gave the customer something to refine with their own stakeholders:
“If you can get your customer engaged in a picture and a story – bought into why it's important – everybody wants to win."
The enablement implication is clear: CSMs need structured practice in discovery, in translating technical outputs into business language, and in building value narratives when customers can't yet articulate what value means to them.
That's a different discipline from product training – and conflating the two is what leads CS leaders to solve the wrong problem.
The four components of a customer success plan that actually works
Christina Parra reviewed hundreds of customer success plans across her eight-year tenure at LinkedIn. The patterns of failure are consistent:
"Three things were happening. We perceived that a customer was receiving value, came to the renewal conversation with this deck, and then the customer said, 'That's actually not why we bought the product. That's not what we mean by value.'"
The second failure: customers weren't receiving value because they weren't holding up their side of the partnership. The third: the plan didn't exist in a form anyone could reference.
Her definition of a success plan is precise for a reason:
"A customer touchpoint where you ultimately answer the question with precision – what are the specific things we must achieve, and how will we know we've done so, to secure your renewal year after year?"
The “why”
The why captures the customer's vision, business objectives, and the value they're expecting from the product. Christina is emphatic that this comes first – not because it's the most interesting section, but because it filters everything else.
"The why comes first because what is actually going to be filtered by the why." Get this wrong and the rest of the plan optimizes for the wrong outcome.
The “what”
The what identifies the leading indicators and behavior changes the product needs to drive — shaped by the specific objectives in the why, not by a generic adoption checklist.
"This is really where you want to put the leading indicators that are measurable and trackable, where you want to put the behavior change that you're really driving into documentation."
The “who”
The who maps stakeholders using a decision-making framework she calls RAPID – recommender, agreeer, performer, input, decision-maker.
Of these, she puts most emphasis on two: "The most important thing when creating a success plan is getting clear on the 'P' – who is responsible for making sure this gets implemented and embedded within the organization – and the 'D' – who is the ultimate decision maker on whether to continue investing."
Multi-threading isn't a nice-to-have here. It's what prevents the plan from dying when a key contact leaves.
The “how”
The how pulls it together into milestones, check-in cadences, and integration with the customer's existing workflows. "This is also where when and where fit really nicely. When are we going to check in again to make sure you're seeing the value that you set out to see? And where – how are we going to integrate this into existing forums?"
What distinguishes Christina’s approach as enablement, rather than just planning methodology, is how she thinks about execution at scale.
She links each component to a specific skill set that managers should be coaching against. Discovery for the why. Multi-threading and stakeholder mapping for the who. Project management and commitment-building for the how:
"Coaching comes down to identifying what skills your team needs to actually deliver a strong success plan."
Standardization matters too, though for a counterintuitive reason:
"When I was a CSM, I was spending a lot of time spinning up templates from scratch, versus going deep on the why, the who, the how."
A consistent format removes that friction and redirects CSMs toward what actually moves the needle.
On portfolio pacing, Christina’s instinct is to start with the question of why not every account has a plan and work backward. "If a CSM is managing 60 accounts, that's one per week if you pace it out. I'd start with the question: why not all 60?"
A lightweight, tailored success plan, she argues, is more valuable than a comprehensive one that never gets done: "Delivering something that is custom but super simple is so much more impactful than delivering something that is really long but not custom."
Grace Gupta
How to build the internal credibility that customer success needs to operate strategically
Ishana Gupta's perspective adds a dimension that Christina and Charlene touched on but didn’t fully address: the internal conditions that determine whether any of this actually sticks.
Ishana joined Darktrace over seven years ago, when customer success was a reactive operations function embedded in the sales organization. She has since built and led the strategic team through three distinct phases: pre-IPO unicorn startup, London Stock Exchange listing, and acquisition by a US private equity firm. Each phase came with different enablement priorities.
In the early stage, the most urgent need was basic customer engagement.
Her team was initially staffed by converting account executives who already had product knowledge and existing customer relationships. KPIs were kept deliberately simple: customer meetings held and executive business reviews completed.
But the training program behind those simple KPIs was more sophisticated. Two initiatives stood out.
Customer Success Collective
1. The problem of the “happiness trap”
The first – what Ishana calls the "happiness trap" – trained CSMs to challenge the assumption that silence means satisfaction.
"You can talk to a customer who says, 'No complaints from our team, everything is going well, we don't need a regular cadence.' And then the renewal comes around and you're thinking – what happened?"
A quiet customer who hasn't realised enough value to complain is a churn risk hiding in plain sight.
2. The problem with structured role play
The second was structured role-play. According to Ishana:
“You can arm your CS org with all the right tools, processes, and product knowledge, but when they go out in the field, it's different.
In our role-play, the manager plays the customer – an end user, a decision maker, a stakeholder – and the CSM has to drive the conversation forward, position themselves as a trusted advisor, and offer solutions that don't cost the customer more money."
As Darktrace matured and went public, the model evolved. The team segmented into strategic, enterprise, and SMB tiers. Compensation shifted from qualitative engagement metrics to renewal quotas. External hiring became deliberate, specifically to introduce diversity of thought.
Ishana’s most distinctive contribution is her argument about internal stakeholder alignment. She advocates for running quarterly internal reviews – with product, sales, and leadership – using the same rigor applied to customer account reviews.
"We always think about our customers and how they measure success,” she notes. “But internally, what does that mean for these stakeholders? How can we help them do their job better and align our goals?"
The reasoning is structural. When leadership changes, as it did significantly at Darktrace through both IPO and acquisition, a CS team that has consistently positioned itself as the organization's powerhouse of customer knowledge becomes a stabilizing force:
"No matter what changed – in sales, solutions engineering, at the executive level – we had established ourselves as a critical resource with trusted customer relationships and deep institutional knowledge."
Her fifth and final takeaway is worth stating plainly: "The answer to your problem is not another tool." Automation matters, operational efficiency matters, but Darktrace ran on a deliberately thin toolset for years. "It's the mindset of being gritty and creative with solutions ultimately," she notes.
Where the three perspectives converge
Three leaders. Three companies. Three growth stages. And a set of shared convictions worth making explicit.
All three treat the customer's definition of value as foundational – not as a given, but as something CSMs must actively uncover and validate.
Charlene builds her entire competency model around it. Christina makes it the first section of every success plan. Ishana trains her team to resist the assumption that the absence of complaints equals delivered value.
In each case, the enablement priority is the same: ensure CSMs can surface what value actually means for each customer, rather than assuming they already know.
All three locate enablement responsibility with leadershipthe , not with a training function. Christina’s coaching framework puts managers at the center of skill development, linking each component of the success plan to a distinct set of behaviors managers should be coaching against.
Ishana’s role-play programme requires managers to actively participate as customer personas. Charlene was candid about pushing back on her executive team when their instinct was to hire differently rather than enable better.
And none of them position tools as the starting point. Ishana says it directly. Christina’s framework is deliberately tool-agnostic. Charlene mentions building a value one-pager and ROI calculator, but frames them as outputs of a well-enabled team – not substitutes for one.
How to audit your enablement across all three layers
The practical test is to audit all three layers, not just the one most visible in your organization.
On capability
Can your CSMs articulate the specific business problem each customer bought the product to solve? Can they build a value narrative when the customer can't give them numbers? If not, the gap probably isn't product training – it's use-case expertise and value fluency. Adding more technical knowledge to a team that can't bridge it to customer outcomes won't move the needle.
On process
Does every account have a success plan both sides can reference? Is it structured around the customer's objectives, or is it a generic checklist mapped to your product features?
Are managers coaching against specific components of the plan, or giving feedback in the abstract? Christina's point about standardization is worth taking seriously: if your CSMs are rebuilding templates from scratch for every customer, they're spending their time on the wrong problem.
On organizational trust: do your internal stakeholders – product, sales, finance, senior leadership – treat CS as a source of customer intelligence? Or is CS still making the case for its own relevance in every cross-functional meeting? If the latter, Ishana’s suggestion of a quarterly internal stakeholder review, using the same structure you'd apply to a customer account review, is worth trying.
The question to ask each stakeholder is a simple one: what does success look like for you, and how can CS help you get there?
Most CS functions are strong in one of these layers, developing in a second and, admittedly, largely ignoring the third. Training a CSM to hold a great customer conversation is necessary, but largely insufficient if there's no process to scale it and no organizational trust to sustain it.
Editor's note: This article synthesizes perspectives shared by Charlene Styers at Customer Success Summit Denver 2025, Christina Parra at Customer Success Summit New York 2023, and Ishana Gupta at Customer Success Summit New York 2025. Details, including job titles and companies, reflect each speaker's role at the time of their presentation.
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