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The Customer Success Guide to Upselling

Matt March 26, 2026

The Customer Success Guide to Upselling

Protect your trusted advisor status while driving expansion revenue.

Watch the Replay
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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.

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"Matt is the go-to professional for elevating sales strategy in education. His trainings are engaging and results-driven. In my twenty years in the business, he's the best I've worked with."

John Kline

Head of Sales, SAM Labs
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"I asked my team to rate Matt's training. The lowest rating was 4.5, and one of my most experienced reps said, '5.5! I’m going to start using this Monday!'"

Allison Duquette

CRO, CampusLogic
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"We're already seeing an impact... He's authentic, he's brilliant, and I would recommend him to anyone who seeks to take their sales skills to the next level."

Tamara Bousquet

EVP Sales, Carnegie Learning

About your trainer.

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As a leading sales trainer for the education technology industry, Matt Gambino partners with edtech sales and marketing leaders to build high-performing teams and scalable sales processes. Rooted in decades of direct experience, his strategies help organizations from startups to market leaders shorten sales cycles and drive revenue. Matt's practical, no-nonsense workshops provide the specific frameworks and language your team needs to win in today's complex edtech market.

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Account ManagementB2B SalesBudget ConversationCSMDiscoveryEdtech SalesLand and ExpandObjection HandlingSales FrameworkSales MindsetSales StrategyValue Selling

My mission is to elevate the edtech industry. I empower sales teams to sell with integrity and impact, and I provide a dedicated haven for teachers navigating their own career journey.

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