What happens when leadership doesn't understand the fundamental differences between customer success and sales? Dillon Young, founder of Lifetime Value Media and host of the Daily Stand-Up podcast, shares hard-won wisdom from 15 years in customer success on this revealing episode of Customer Unsuccess.
At the heart of many CS struggles is a critical misunderstanding: sales operates in the realm of expectations while customer success deals with experiences. As Dillon explains, "In sales, it's all about expectations. You can sell a dream because customers have no basis for understanding what you can actually deliver." But when renewal time approaches, customers have accumulated a year of real experiences with your product, making empty promises worthless.
This disconnect creates painful scenarios where CS teams are left managing disappointed clients who realize they're not getting what they were sold. Dillon shares a powerful story about confronting leadership over a top-performing salesperson who consistently sold "vaporware" - wasting implementation resources and guaranteeing eventual churn. Despite the obvious damage to the company's reputation and customer retention, leadership hesitated to address the issue because of short-term revenue targets driven by investor demands.
The conversation explores practical strategies for success despite these challenges. Both hosts advocate for a "default to action" approach - starting with small, imperfect solutions rather than attempting to build comprehensive systems from scratch. As Dillon suggests, "If replacing a tool later would be relatively simple, don't spend more than 30 minutes deciding which one to implement." This philosophy prevents analysis paralysis and keeps teams moving forward through experimentation.
Ready to transform your approach to customer success? Subscribe to Customer Unsuccess for more candid conversations about what doesn't work in CS—and how to turn those failures into your greatest opportunities for growth.

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