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You wouldn’t propose on the second date. (Unless you’re on a Netflix reality show – in which case, congrats, and I’m watching.)
So why are we still treating Customer Success like a string of random check-ins, awkward upgrade pitches, and last-minute “please don’t churn” Hail Marys?
Let’s call it:
Most CS motions in 2025 are still running on hope, habit, and a handful of vanity metrics.
This isn’t scale. It isn’t strategy. It’s survival mode with a fresh coat of branding.
The fix? A motion that’s always-on, outcome-first, and impossible to ignore – where expansion is planned, renewals are earned, and every touchpoint moves the customer toward their goals.
Here’s the playbook.
Too many Customer Success teams treat expansion as a one-off event, something you “bring up” at the end of a Quarterly Business Review or, worse, as a last-minute upsell during renewal negotiations. This approach almost always feels awkward to the customer and puts you in a defensive position.
Expansion isn’t a pleasant surprise you spring on a customer. It’s not a quick add-on to close out the quarter. It’s a strategic step in a long-term relationship, more like a marriage than a casual date. For an expansion to feel natural, it must be the culmination of trust, value, and shared goals established over time.
That means changing the approach from opportunistic to embedded.
Here’s how to make expansion an organic part of the customer journey:
When expansion is treated as a continuous thread – woven into every interaction and milestone – it stops feeling like a “big ask” and instead becomes the obvious next step in a successful relationship.
In many Customer Success teams, “low touch” has become a polite way of saying, we disappear for most of the year and hope the customer renews.
It’s an easy trap to fall into, especially when teams are under pressure to cover large account volumes or operate “efficiently.” But the reality is that this approach isn’t efficient at all. It’s reactive account management disguised as scale.
When you only show up as the renewal date approaches, you’ve already missed most of your opportunities to reinforce value, deepen relationships, and influence the outcome. At that point, your renewal conversations become high-stakes negotiations rather than low-stress affirmations of a healthy partnership.
The best-performing CS teams take a completely different approach: they build a steady, proactive presence into the customer experience. That doesn’t mean overwhelming the customer with unnecessary meetings or flooding their inbox. It means showing up at the right moments, with the right insights, to drive progress toward their goals.
Practical ways to replace ghosting with meaningful engagement:
Staying visible and valuable throughout the lifecycle doesn’t just protect renewals — it creates the conditions for consistent expansion. Customers who feel seen and supported are far more likely to grow with you, rather than shop for alternatives.
For years, Customer Success teams have relied on red–yellow–green health scores to gauge account risk. On the surface, it feels logical: Green means all is well, yellow means caution, and red means trouble. The problem? Reality rarely matches the colors.
You’ve probably seen it yourself:
That’s because most traditional health scores are decorative, not predictive. They’re often based on superficial activity metrics – like logins, email opens, or NPS scores – rather than a true measure of whether the customer is achieving meaningful outcomes.
If you want a health score that actually helps you retain and grow customers, it needs to be tied to the things that truly signal long-term success.
What to focus on instead:
When your health score is tied to impact rather than activity, you stop guessing at which customers are truly at risk, and you give your team a reliable tool to prioritize their time where it will make the biggest difference.
The Quarterly Business Review is a staple in most Customer Success playbooks, but in many cases, it’s a ritual that delivers more fatigue than value. Too often, QBRs become a glorified product update: a slide deck of usage graphs, feature release notes, and recaps of things the customer already knows.
When that happens, you’re asking senior stakeholders to give you an hour of their time without giving them anything meaningful in return. That’s not just a wasted opportunity — it’s a slow erosion of your credibility.
A QBR should be one of the most strategic touchpoints in your relationship. It’s your chance to:
If your QBR isn’t doing that, you’re better off replacing it with a short, targeted update that frees up the customer’s calendar.
How to turn QBRs into high-value conversations:
When your QBR delivers actionable insight, proves value, and moves the customer closer to their goals, it becomes a growth engine rather than a calendar obligation. And if it doesn’t? Cancel it — and spend that time delivering results they’ll notice without a meeting invite.
Most customer journey maps look impressive in a slide deck – neat rows of touchpoints, stage names, and colorful arrows pointing from “Onboarding” to “Adoption” to “Renewal.”
The problem? These diagrams often reflect how your company wishes the relationship would unfold, not the reality your customers actually experience.
In practice, customer journeys are rarely linear. They’re full of detours, slowdowns, skipped steps, and moments where value is either accelerated or lost altogether. When your strategy is based on the idealized version rather than the lived experience, you risk missing the real opportunities and threats that shape retention and expansion.
A better approach: Create a reality map, one that reflects what customers are actually doing, feeling, and trying to accomplish at each stage, even if it doesn’t match your neat process flow.
How to shift from fantasy to reality:
When you manage the reality instead of the ideal, you gain a far more accurate view of risk, a better sense of where to focus your resources, and more opportunities to deliver unexpected wins, the kind that build loyalty and open doors to growth.
One of the least effective habits in Customer Success is the “just checking in” email. It’s vague, low-value, and puts the burden on the customer to decide whether there’s anything worth discussing. Over time, it also conditions them to see your outreach as optional, or worse, interruptive.
Your role as a CS professional isn’t to be a friendly presence in their inbox. It’s to be a strategic partner who consistently moves them closer to their goals. Every interaction you initiate should have a clear purpose, tied to a meaningful customer outcome.
The mindset shift is simple: stop thinking in terms of check-ins and start creating checkpoints – intentional moments where you review progress, resolve friction, and introduce the next step forward.
How to make the switch:
When you frame outreach as a value delivery moment rather than a courtesy call, customers see you as indispensable, not just during onboarding or renewal season, but throughout the entire relationship.
The era of reactive, ritual-driven Customer Success is over. Customers don’t renew or expand because you showed up at the right calendar interval. They do it because you’ve consistently proven that your product – and your partnership – drives their success.
In 2025, that means:
This isn’t about adding more meetings, more reports, or more noise. It’s about building a motion that is always on, always valuable, and always aligned to what the customer is trying to achieve.
When you operate this way, renewal stops being a cliff-edge moment. Expansion becomes a natural next step. And your CS team shifts from being a cost center to a revenue driver, without the Hail Marys, the guesswork, or the ghosting.
Stop hoping customers will stay. Build the motion that makes staying – and growing – the obvious choice.
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About the author:
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Stijn Smet is the Head of Customer Success at Whale and one of the industry’s most recognized CS voices. As the host of the Customer Success Hotline and We Fucked Up So You Don’t Have To podcasts, he’s known for his bold, practical take on onboarding, retention, and revenue growth. With years of hands-on experience across global CS roles, Stijn is passionate about elevating the profession and helping teams deliver real, measurable customer impact.
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