The Customer Success Guide to Upselling
Protect your trusted advisor status while driving expansion revenue.

Turn your routine client check-ins into natural revenue drivers.
You’ve built incredible, trusting relationships with your clients. But lately, expectations have shifted. You're no longer just responsible for putting out fires and securing renewals—you're expected to actively upsell and cross-sell.
The problem? Your clients can be forgiven for viewing you as a customer support rep rather than a strategic partner. When you try to introduce a new product or service, you immediately hit walls like "we don't have the budget" or "it's not a required need". Worse, your main contact is often reluctant to introduce you to the actual decision-makers in the central office. You want to hit your numbers, but the thought of deploying a "hard sell" feels like it will destroy the relationship you've worked so hard to build.
Stop pushing products and start providing undeniable insight.
Key frameworks and takeaways
In this free on-demand session, I’ll teach you how to flip the script. You will learn how to step into a new mindset where you care less about "selling" and care much more about the value of your advice. You will learn:
- The Identity Shift: Why you must mentally rebrand yourself from a reactive "Customer Success Manager" to an objective, indispensable "Research and Advisory Professional".
- The Third Agenda Item: A highly effective, low-pressure way to introduce industry insights into your standard check-ins, seamlessly opening the door for mini-discovery.
- The Capability Matrix: Why you need to stop socializing product features and start focusing on "capabilities"—empowering a specific person to take a specific action at a specific point in time.
- The Numbers Quadrant: How to comfortably ask the right questions to help your clients quantify the massive financial cost of their problems (like teacher turnover or lost funding).
- The "Cost of Proof" Trade-Off: A professional, entirely fair method to finally secure that introduction to leadership (like the Provost or Assistant Superintendent) by offering them a customized deep dive into your solution.
You will leave this session with a repeatable framework to protect your hard-earned relationships while confidently navigating discovery. You'll know exactly how to guide your next client meeting so that your customers naturally recognize the financial value of your expansion solutions.
Feedback from industry leaders.

John Kline

Allison Duquette

Tamara Bousquet
About your trainer.

