The Customer Success Guide to Upselling
Your role is expanding. But you shouldn't have to become a pushy vendor.
If you’re in edtech Customer Success right now, you know the reality on the ground. Institutions are facing budget cuts. Companies are scrambling to hit revenue targets. And increasingly, leadership is looking at you to bridge the gap. You are being asked to cross-sell, upsell, and drive revenue—skills that likely fall completely outside of what you were hired to do.
You shouldn't have to navigate this transition by trial and error.
This training removes the pressure of the hard sell. It focuses on discovery. It is about proving you can uncover new opportunities—not with "20 questions" but by leveraging your talent as a credible problem-solver. In this session, I am going to teach you how to pivot your existing meetings, protect your trusted advisor status, and turn your routine check-ins into natural revenue drivers.
Key frameworks and takeaways
The QBR Pivot
How to seamlessly transition from a standard check-in or Quarterly Business Review into a strategic discovery conversation without making it feel forced.
A Research & Advisory Mindset
How to protect your status as a genuine partner and advocate for the institution while actively identifying and qualifying new revenue opportunities.
Managing the Fiscal Reality
Specific techniques for handling the immediate objection of "we have no budget," and how to reframe your upsell as the solution to their most pressing education challenges.
Graceful Handoffs
The exact framework for smoothly handing off the opportunity to an AE, or closing it yourself, without ever resorting to a hard sell or awkward closing tactic.
This training is for...
Customer Success Managers:
Account Managers:
Enablement Leaders:

