Customer success doesn't start at kickoff. It starts the moment a prospect raises their hand.
The conventional wisdom in SaaS is that customer success begins at kickoff — the moment a contract is signed and the handoff from sales happens. But that thinking creates one of the most damaging gaps in the entire customer lifecycle: the expectation chasm. When CS teams aren't involved until after the deal closes, they inherit promises they didn't make, commitments they didn't set, and customers who are already measuring the relationship against a standard that may be impossible to meet.
The pursue stage — the period when a prospect is evaluating your product, running a proof of concept, or negotiating terms — is actually the most formative window in the entire customer journey. The conversations that happen here establish the emotional baseline. Prospects decide whether they trust you, whether you understand their business, and whether your team has the operational depth to back up what sales is promising.
CS involvement in pre-sales isn't a "nice to have" in modern enterprise software. It's a structural advantage. When CSMs participate in discovery calls, POC design sessions, and executive briefings, they close a feedback loop that benefits the entire organization: sales closes better deals, CS inherits healthier accounts, and the customer gets a team that actually knows what they signed up for.
Misaligned expectations at the close of a deal don't just create awkward kickoff calls — they cost companies real money. Research consistently shows that the number one driver of early churn isn't product deficiency; it's expectation mismatch. When a customer signs a contract believing your product will solve a problem it was never designed to solve, no amount of post-sale effort will save the relationship.
The misalignment usually isn't malicious. Sales teams are under pressure to close, and they want to paint the most compelling picture possible. But without a CS partner in the room to reality-check commitments, certain promises start creeping in: unrealistic timelines, overstated integrations, implied support levels that don't exist. By the time the customer meets their CSM, the damage is already done.
The financial impact compounds quickly. At-risk accounts require disproportionate CSM time. They escalate more. They churn sooner. And when they do churn, they leave reviews that poison future pipeline. The best time to prevent a bad churn story is before the deal ever closes — and that means getting CS in the room during the pursue stage.
In most organizations, the pursue stage is entirely owned by sales. AEs lead discovery, SEs run technical demos, and a deal desk negotiates the contract. CS waits by the phone for the Closed Won notification. Changing this pattern requires both process redesign and cultural buy-in — and it starts with defining what CS actually does during pursuit.
At a minimum, CS should be introduced to the prospect during the late stages of evaluation. This introduction signals organizational maturity: the customer isn't just getting a salesperson who will disappear after signing — they're meeting the team that will own their success. It also allows the CSM to begin building relationship equity before the ink dries.
More advanced organizations bring CS in even earlier — during POC design and discovery. The CSM participates not to close the deal, but to understand the customer's true operational environment: who owns the tool internally, what their existing processes look like, where the political landmines are, and what "success" means to different stakeholders. This intelligence becomes the foundation for everything that follows.
A proof of concept is more than a technical exercise. It's the first real test of what the working relationship will feel like. Customers pay attention to how you design the POC as much as whether the technology works. A chaotic, poorly scoped POC — even one where the product performs perfectly — signals to the buyer that the post-sale experience will be similarly disorganized.
A CS-led POC framework starts with clarity of scope. Before a single environment is configured, the CS team should help facilitate a conversation that answers four questions: What business outcome are we trying to demonstrate? Who will be evaluating success? What does "pass" look like, and what does "fail" look like? And what's the timeline? When these questions go unanswered, POCs become open-ended exercises that exhaust everyone and rarely lead to confident decisions.
The CSM's role during the POC isn't to run the technical implementation — that's typically a SE or implementation specialist. The CSM facilitates the business conversation, ensures stakeholder alignment on success criteria, and begins building the relationships with champions and economic buyers that will become critical during onboarding. Done right, the POC becomes the first chapter of the customer success story.
One of the most powerful things a CS team can do during the pursue stage is help the customer articulate what success looks like in concrete, measurable terms. This sounds simple, but it's surprisingly rare. Most buyers have a vague sense that the product should "improve efficiency" or "reduce churn" — but they haven't translated those aspirations into specific metrics with owners and deadlines.
The CSM's job is to push on that vagueness — not aggressively, but with genuine curiosity and professional structure. Questions like "How are you measuring that today?" and "What would a 20% improvement in that metric mean for your business?" and "Who in your organization cares most about that number?" transform fuzzy aspirations into the kind of specific success criteria that can actually be tracked and celebrated.
This process also surfaces misalignment. When the VP of Sales says "I want to reduce customer churn" and the Director of IT says "I want to consolidate our tool stack," those may point toward very different implementations. The earlier the CSM surfaces that gap, the better — because resolving it pre-sale is infinitely easier than resolving it six months into a stalled deployment.
Enterprise deals involve multiple stakeholders, but the most important relationship in the pursue stage isn't with the champion — it's with the economic buyer. This is typically an executive who controls budget and ultimately decides whether the contract gets renewed. If this person doesn't understand what they're buying, why it matters, and how success will be measured, the relationship is fragile from day one.
CS teams can play a critical role in facilitating executive alignment during the pursue stage. An executive briefing gives the CSM an opportunity to speak the language of business outcomes rather than product features. Rather than walking through the product roadmap, the conversation centers on: Here's what we've seen work for customers in similar situations. Here's what the first 90 days would look like. Here's how we'll measure and report on value.
This conversation also serves a critical intelligence function. It reveals the executive's real priorities, their risk tolerance, their internal pressures, and their appetite for change. All of this becomes invaluable context as the CSM builds the post-sale success plan.
One of the most impactful tools a modern CS organization can deploy in the pursue stage is the customer charter: a structured document that captures the goals, success criteria, stakeholders, and mutual commitments agreed upon before the contract is signed. Think of it as the operating agreement for the customer relationship — the shared source of truth that everyone can point to when questions arise.
A well-built charter typically includes: the customer's stated business outcomes; the specific metrics that will be used to measure success; the key stakeholders on both sides with their roles and responsibilities; the high-level implementation timeline; and any known constraints or dependencies that could affect outcomes. It's formally acknowledged by both parties before the deal closes.
Charters serve a powerful dual function. First, they force clarity: if you can't fill out a charter, you don't yet understand the deal well enough to close it confidently. Second, they create accountability: when the customer is unhappy six months later, the charter is the document that grounds the conversation in what was actually promised — and what was actually delivered.
Even CS teams that are philosophically committed to pre-sales involvement make predictable mistakes. The first is showing up too late — getting introduced in the final week of negotiation rather than during evaluation. By that point, the customer's mental model of the product is already fixed, the champion relationships are already formed, and the CSM is playing catch-up from day one.
The second mistake is treating the POC as a technical exercise rather than a relationship-building opportunity. Technical POCs where the CSM is absent miss the chance to establish trust, gather context, and start building the human connections that carry the relationship through difficult moments in the post-sale period.
The third — and perhaps most damaging — mistake is allowing sales to set commitments the CS team can't keep. CS teams need a voice at the table to flag when commitments are unrealistic, when timelines are aggressive, or when the customer's use case falls outside what the product actually does well. That voice has to be present and empowered to push back — politely, professionally, but firmly.
How do you know if your pursue stage is healthy? A few key metrics offer visibility. First, track CSM introduction rate: what percentage of deals above a certain ACV threshold include a formal CSM introduction before close? If that number is below 80%, you have a structural problem worth addressing immediately.
Second, track expectation alignment scores. Some organizations implement a brief internal survey at handoff — where the CSM rates how well the customer's expectations match what the product can actually deliver. Accounts that score low on alignment at handoff should immediately trigger a pre-onboarding alignment meeting rather than proceeding directly to kickoff.
Third, track early churn correlation. Do accounts where CS was involved in pre-sales have lower 6-month churn rates than those where CS was not involved? In almost every organization that measures this, the answer is yes — often dramatically so. This data is your business case for investing in pursue-stage CS involvement.
The pursue stage sets the tone for everything that follows. It is where trust is either built or eroded, where expectations are either calibrated or inflated, and where the customer either begins to see you as a long-term partner or as a vendor they'll replace the moment something better comes along.
Organizations that treat the pursue stage as purely a sales problem are leaving one of their greatest retention levers untouched. The customers who renew most reliably, expand most aggressively, and advocate most vocally are almost always the ones who felt understood before they ever signed — where the post-sale team was present and engaged from the very beginning.
Customer success in the pursue stage isn't about closing the deal. It's about making sure the deal that gets closed is one that can actually succeed. That discipline — the willingness to walk away from bad fits and shape good ones — is what separates great CS organizations from everyone else.
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