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CRO Better Ep #01: The Future of Customer Success and Revenue Leadership
In this inaugural episode of of CRO Better, RevPartners CEO Brendan Tolleson sits down with HubSpot's SVP of Customer Success, Jon Dick, to discuss Jon’s journey from marketing to customer success, the evolving role of customer success and sales outreach in the age of AI, the importance of clean infrastructure, and how targeted messaging can improve engagement.
Check it out! 👇
5 Minute Rundown:
Deliver > Delight: The New CS Mindset
Jon: “In 2025, deliver is the new delight. You’ve got to deliver value—that’s the best way to delight a customer today.”
Customer Success is no longer about simply making users happy. It’s about consistently delivering real, measurable value. It’s not enough to delight customers with friendly service or helpful tips; what matters is whether they’re actually seeing results.
The focus now is on driving adoption, stopping downgrades, and preventing cancellations. If customers aren’t seeing tangible value, they’ll leave, and in today’s fast-paced market, they’ll do it quickly.
AI: The Secret Weapon for Smarter CS
Jon: “I can actually create a fully customized email for you that analyzes your usage of the product and makes recommendations.”
AI has become the ultimate sidekick for Customer Success teams. It bridges the gap between scale and personalization, using data to craft unique customer experiences that would be impossible for humans to manage alone.
From analyzing product usage to recommending specific next steps, AI empowers CS teams to focus on high-value conversations while still maintaining a personal touch. Automation handles the heavy lifting, freeing up time for deeper, more meaningful interactions.
Forget Platform Lock-In. It’s About Value Lock-In
Jon: “The only real lock-in now is delivering so much value that people don’t want to switch.”
The era of platform lock-in is over. AI has made switching software easier than ever, cutting down migration costs and simplifying the entire process. That means the old reliance on complex setups and high switching barriers no longer works.
The only way to truly retain customers now is by delivering constant, undeniable value. If the product keeps solving problems and driving results, customers won’t want to leave, even if it’s easy to do so.
Everboarding: CS Doesn’t Stop After Setup
Jon: “We think about everboarding more than onboarding now… you’ve got to keep driving value.”
Onboarding isn’t the end goal anymore, it’s just the beginning. Success teams need to focus on “everboarding,” a continuous process of educating and engaging customers long after they’ve gone live.
It’s about helping users get deeper into the product, adopt new features, and consistently unlock more value. Continuous guidance ensures that customers don’t just start strong but stay strong, reducing churn and driving long-term growth.
CS + Product > CS + Sales
Jon: “We’ve spent more time aligning CS with our product partners than our sales team—because better products create better customer outcomes.”
Traditional models tie Customer Success closely to sales, but a stronger approach aligns CS directly with product teams. When CS teams have direct insight into product roadmaps and updates, they’re better equipped to help customers maximize value and deepen adoption.
Instead of focusing on upsells, the priority shifts to helping customers succeed within the platform, naturally leading to growth and retention without the hard sell.
Deliver Value. Drive Growth. Keep Customers.
Retention isn’t luck, it’s strategy. The BowTie Model shows you how to focus on what actually delivers value and pulls the right levers for sustainable growth.