The Cost of Poorly Led Customer Success Execution in SaaS

In my work with SaaS companies, one pattern is painfully clear: great sales can’t save broken Customer Success. In the subscription-based SaaS world, customer retention isn’t just a metric – it’s the lifeblood of sustainable growth. When Customer Success (CS) is executed poorly, the impacts on retention and Annual Recurring Revenue (ARR) are profound. High churn rates drain revenue and stifle growth, forcing companies to replace lost ARR just to stand still. In contrast, strong customer success practices boost retention, expansion, and profitability. This analysis reflects what I’ve seen firsthand working with many SaaS organizations trying to bridge the gap between value-based selling and Customer Success. Flawed CS execution – whether due to inadequate frameworks, weak leadership, or inexperienced talent – doesn’t just damage relationships, it undermines your revenue model. I’ve watched great products underperform because the CS strategy was reactive, misaligned, or underfunded. And I’ve also seen companies reverse serious churn problems simply by investing in the right people and process to make Customer Success a core business driver.

Why Seasoned CS Leadership Matters

Seasoned Customer Success (CS) leadership at the CCO, SVP, or VP level can make or break key SaaS outcomes. Poor leadership in this role often has dire consequences for customer retention, expansion, and ultimately ARR. On the flip side, an experienced CS leader can unlock efficient growth through expansions and cross-sales. I’ve worked with companies on both ends of this spectrum – those with mature, data-driven CS leaders who orchestrate growth through intelligent plays, and others where CS is still treated as a reactive support layer.

Poor leadership increases churn and stunts growth: Weak or inexperienced CS heads often default to reactive “firefighting” rather than strategic customer programs. This leads to preventable churn and missed expansion opportunities. I’ve seen teams burn out from running save plays at the eleventh hour because they lacked early warning systems or clear success plans. It doesn’t take long for this to erode trust internally and with customers. Just a 1% drop in retention can significantly damage company value (and inversely, a 1% improvement boosts it). One company I consulted with lost 5% of ARR from a single surprise churn – the impact was felt across finance, product, and sales. In contrast, I’ve helped organizations stabilize and grow NRR just by redesigning their segmentation and engagement model. The delta? Strong, accountable leadership at the top.

The right CS leader: internal promotion vs. external hire: There’s a real decision point here, and I’ve advised executives on both paths. Internal candidates often bring the trust and tribal knowledge needed to navigate complexity. But when you’re trying to scale or transform CS into a proactive function, you sometimes need fresh DNA. The best external CS leaders I’ve seen come in with operating rigor – they’ve owned NRR before, they’ve built from $10M to $100M, and they know how to build repeatable motion across teams. The worst? People who mistake “being great with customers” for being a strategic operator. The truth is, effective CS leaders today are commercial, data-savvy, and deeply cross-functional. They don’t just advocate for the customer – they advocate for the business through the customer.

Driving upsells, cross-sells, and efficient growth: This is where the best CS organizations shine. The cost to acquire new customers is only going up – CAC is up 60%+ over the last five years. But CS teams have a lever that’s 4–5x more efficient: expansion. I’ve helped teams rewire their onboarding and success planning to set up expansion plays from day one. When CS and Sales align on customer value – not just usage or activity, but real business impact – cross-sell and upsell become a natural next step, not a surprise pitch. One client I worked with increased expansion ARR by 30% within two quarters, simply by enabling their CS team to lead strategic roadmap reviews and surface unmet needs. But again, this requires CS leaders who think like GTM execs, not just service leads.

Each of these points underscores why having an experienced CS leader is vital. Poor leadership at the top of Customer Success leads to churn, missed revenue, and erosion of ARR, whereas strong experienced leadership secures renewals and unlocks growth in a cost-efficient way. In a SaaS business where, as one SaaS veteran put it, “customer success is where 90% of the revenue is,” investing in seasoned CS leadership isn’t a luxury – it’s a necessity for retention and long-term growth.

It's worth recognizing that while Customer Success was seen by some as a 'made-up' job family when it first emerged 15 years ago, it has now proven to be every bit as essential as traditional functions like Finance, Accounting, or Operations. From my seat as a consultant, I see the best CS professionals exhibit the same rigor and strategic thinking you’d expect from a CFO or COO. They don’t just keep customers happy – they understand the cost structure, the segmentation model, and the levers to pull for scale.

High-performing CS professionals exhibit a mix of analytical rigor, commercial acumen, and cross-functional leadership. But with Customer Success gaining so much traction, it’s also a space that’s getting noisy. Not every CS leader who claims success has the depth or repeatability to back it up. I always advise clients to carefully vet backgrounds — look beyond the buzzwords and dig into what measurable results they've actually delivered. Have they consistently moved NRR? Scaled a team? Navigated complex segments? It's easy to talk customer-centricity; it’s harder to prove it with outcomes. The most effective CSMs and CS leaders I’ve partnered with typically come from sales, consulting, analytics, or product. They marry those disciplines with a deep customer-first mindset. No number of degrees can replace this. They’re fluent in metrics like NRR, understand how to segment and prioritize accounts, and can communicate value in a boardroom as easily as they can troubleshoot with a frontline user.

As the CS function has matured, it's also become clear that these professionals drive impact beyond churn mitigation. They reduce the cost of selling by driving expansion from within the customer base — an inherently more efficient growth motion than net-new acquisition. Studies consistently show that it's 60–70% easier to sell to an existing customer than to acquire a new one, and top CS teams enable this by surfacing insights, building trust, and timing conversations around real customer outcomes.

Customer Success has earned its place not just alongside, but embedded within the strategic core of a SaaS company. One reason it’s so unique—and so complex—is that CS isn’t confined to a single swim lane. Unlike many traditional functions that operate in a defined vertical, CS has to work laterally across the organization. That means aligning with Sales on handoffs and upsells, with Product on roadmap gaps and feature usage, with Marketing on customer advocacy, with Finance on forecasting retention and NRR, and with Support on reactive coverage. The best CS leaders I've worked with can influence all of these teams without formal authority. It's one of the only roles that must orchestrate success across silos. That complexity isn’t always visible on paper—but it’s a huge part of why Customer Success, done well, changes the entire trajectory of a SaaS business.

As Leonardo da Vinci once said, “Realize that everything connects to everything else.”— Leonardo da Vinci. This perfectly captures the CS mandate—unifying teams, data, and outcomes across the organization to ensure the customer wins, and the business grows because of it. It is no longer a side function—it’s a force multiplier across revenue, product, and customer loyalty. The most successful SaaS companies know this and build accordingly. And in my experience, those who don’t? They end up trying to solve revenue problems too late—because they ignored the product, support or post-sale motion until it broke.

If you're building or rethinking your CS org and want perspective on what works—and what to avoid—I'm always open to a conversation. Successful growth is a passion of mine avoid the noise.