Challenges Faced by Customer Success Leaders

The average tenure of a VP of Customer Success? 18 months. Ask a CS leader why, and they'll tell you: unrealistic expectations. Ask a CEO, and they’ll say: failure to meet expectations. Who's right? Both. CEOs set aggressive goals but don’t always understand what it actually takes to achieve them. CS leaders want to rise to the challenge but often fail to educate and manage up. The result? A giant game of misalignment and unmet expectations. But here’s the thing—both sides want the same outcome: 🟢 Customers who stay. 🟢 Customers who grow. Having been on both sides of this, I’ve seen it done right—and painfully wrong. If I were stepping into a CS leadership role today, here’s how I’d bridge the gap: 1️⃣ Get Clear on the Goals Before running full speed ahead, sit down with the CEO (or senior exec). Look at the data and align on goals. But—newsflash—where you’re starting from matters. You can’t promise to hit a 130% NRR when retention is tanking at 85%. Aligning on the baseline ensures you’re setting a strategy, not a fantasy. 2️⃣ Analyze the Data You can’t fix what you don’t understand. Before you start building a 42-step CS strategy, figure out: ❓ What’s actually driving churn? ❓ Where are the biggest risks? ❓ What will move the needle fastest? If adoption is the biggest issue—your focus isn’t just “more QBRs.” It’s training, enablement, and change management. Solve the right problem. 3️⃣ Keep It SIMPLE CS leaders love to overcomplicate things. (Guilty.) But here’s the truth: Good today > Perfect six months from now. Start small. Run a pilot. Test and learn. Execution beats perfection every time. 4️⃣ Align on Leading Indicators NRR and GRR are great—except they’re lagging indicators. If you wait for those numbers to move, it’s already too late. Instead, track: ✔️ Expansion pipeline growth ✔️ Health score trends ✔️ Early-stage adoption signals Catch issues early. Pivot fast. 5️⃣ Iterate or Pivot As Needed If something isn’t working, fix it fast. There’s no trophy for sticking with a bad plan just because you wrote it down. Make data-driven decisions. If the signs are there, adapt before it’s too late. 6️⃣ Communicate (Early & Often) Execs don’t need every little detail. But if you’re not proactively sharing progress, they’ll make up their own story. ✔️ Weekly or bi-weekly updates ✔️ Regular check-ins ✔️ A clear, consistent narrative When there’s silence, assumptions win. And assumptions are rarely in your favor. CS isn’t like Sales, Marketing, or Finance—it’s still a black box for many execs. Your job is to demystify it. Set expectations. Educate. Show impact. Manage up. This won’t solve everything—but it will make things a lot better. _________________ 📣 If you liked my post, you’ll love my newsletter. Every week I share learnings, advice and strategies from my experience going from CSM to CCO. Join 12k+ subscribers of The Journey and turn insights into action. Sign up on my profile.

Customer success has a problem. According to Bain’s Customer Success Practitioner Survey 2024, 60% of B2B SaaS companies have a customer success team within their organizations. And yet, net revenue retention is dropping like a led balloon. According to the survey, two thirds of customers believe their needs are only *moderately* being met, or worse. And to make matters worse, there’s a disconnect between what vendors think customers want and what they say they need. Just look at the graphic below. Customers’ TOP priority is technical assistance implementing the product. When asked, companies prioritize the same need LAST. How can this be? How can companies be so disconnected from the voice of their customers? Here are the fundamentals you need for customer success: 1/ Specialized implementation and onboarding  Dedicate people to every customer or build onboarding into the product. 2/ Fantastic support This is the "dial tone" of customer success. Always on, always reliable, always fast and helpful for customers. Yes, we need to engage with customers proactively but don't underestimate the power of a quick, high-quality response when a customer has an acute need. 3/ Intuitive products The Bain article address it, but software products—especially enterprise software—needs to be better. Better fit to purpose. Better usability. Easier to implement and configure. And not only the physical product, the documentation, self-serve resources, support, and services around it. The *whole* product. Product development must pursue customer success goals, not just blindly ship feature after feature. 4/ Account management Implement proactive account management with a bent toward customer success. Teach these folks how to do value creation plans and business reviews, but also give them commercial responsibility for growing accounts. The best account management teams have always done these things. In 2024 these expectations aren’t too high. I’ve seen so many companies build huge customer success teams to fill the gaps in the product and give a high-touch experience to top customers. It doesn’t work because human knowledge doesn’t scale unless it’s written down, or better yet, built into the product. If you’ve followed me for any time, you know I’m an advocate of customer success—the OUTCOME. But many customer success *teams* need a major makeover. Generic, high-level, jack-of-alll-trades CSMs just won’t cut it anymore, and it's a drag on your P&L. The data in the Bain report tells the story. How are you addressing this in your company? — 📨 Jeff and I publish a weekly newsletter (free) for Chief Customer Officers and those who aspire to the role. We address issues like this which threaten to limit the success of SaaS companies. Details ⬇️ #customersuccess #saas #sales #product Jay Nathan GrowthCurve

I’ve lost count of the number of CS leaders that let me know they’ve been fired for poor retention. At the same time, I can’t remember the last time a product or engineering leader was fired for the same reason. Or a CEO. Critical board-level business metrics (ARR, NRR, GRR) are not delivered solely by one person or team. A CS leader can only control what they can control. 1) They can’t control if their competitors have better products.  2) They can’t control if the market thinks their product is a nice-to-have.  3) They can’t control if their budget has been shrunk in half by the CFO and are now barely scraping by w/ headcount to implement a technical & complex product with long time-to-value. 4) They can’t control if the product is buggy and unreliable.  5) They can't control if the customer shouldn't have been sold in the first place and was outside core ICP. What can they control? ♦️ Understanding customer-required outcomes in the sales to CS handoff process and understanding how they evolve throughout the Customer Maturity Model (aka customer goals change quarterly along with where they are in your value realization journey). ♦️ Delivering on those outcomes unique to the customer persona (a BTL individual contributor has different outcomes than an ATL decision maker) ♦️ Delivering multi-channel campaigns to each customer persona and A/B testing delivery & conversion. (aka, stop sending the same cookie-cutter emails that people don’t even read) ♦️ Tracking if the plays they are running are actually working or not. ♦️ Tracking customer health in a way that aligns with forecast methodology. Real health is not solely defined by usage and NPS alone. The reality is that the feature they are using... can be used somewhere else. Usage must be explicitly correlated to the decision maker's quarterly OKR. You must be solving real business problems if you want to be 'sticky.' An important pressure test question to ask yourself: What does my customer's CFO think about the product positioning and value messaging? Are my CSMs and content/messaging programs aligned to that? If they tried today, could they replicate your value somewhere else, cheaper? If so, there is major risk here awaiting you. ♦️ Recording CSM calls and training them on a weekly basis. Ensuring CSM teams are leveling up in Command of the Message, negotiation techniques, happy ears, give/get, deep discovery, etc. ♦️ Running proper renewal inspection with rigor and process. (aka not using next steps fields that are outdated).   If the VP of CS is not doing the above, then perhaps it’s time to replace them.  If the VP of CS is doing the above.. then you don't have a CS problem. You have a business problem. #sales #customersuccess #ceo