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Semester 2, Session 5: Maximize Deal Size by Selling Value

Summary

In this high-impact session, Chris Smith lays out a proven framework for MSPs to Maximize Deal Size by Selling Value from tactical selling. You’ll learn how to present clear, transparent pricing (small, medium, large). You’ll also see how to uncover hidden opportunities through better discovery, and reframe CRM as a business growth engine—not just a tool.

With real-world strategies that drive 10x revenue for MSPs who lead with Dynamics, this session shows how to build trust, justify bigger deals, and differentiate in a crowded market.

Flip the Script to Win Bigger Deals

In this standout moment, Chris Smith shares how ditching the traditional “scope-then-price” model for upfront, transparent packages transformed his deal flow. Instead of losing prospects to sticker shock after weeks of discovery, this approach builds confidence early. It makes it easier for buyers to commit to larger deals.

This clip is a clear example of value-based selling in action—but it’s just the beginning. In the full session, you’ll learn how to design your own tiered offers and apply the strategy behind landing larger, better-aligned customers—faster.

Uncover the Real Opportunity with Better Discovery

This clip explores a subtle but powerful sales skill: asking why. When a prospect says “we need X,” there’s often a bigger opportunity beneath the surface. Chris explains how thoughtful discovery and curiosity can reveal a need for Y, Z, and more—turning a one-off sale into a multi-phase engagement.

If you’re only selling what customers ask for, you’re leaving revenue on the table. Watch the full session to see how great questions lead to great deals—and how to make this a repeatable part of your sales motion.

Transparency Builds Trust—and Bigger Packages

Chris shares a tactical 90-day plan to increase your average deal size. It starts with retrospectives and ends with packaged, outcome-focused offerings. This clip highlights what customers really want—clarity, predictability, and confidence in your process.

Transparency isn’t just ethical—it’s strategic. In the full session, you’ll learn how to create your own “small/medium/large” options that make buying easier, boost close rates, and lay the groundwork for long-term growth.

Sell Outcomes, Not Technology

This direct and essential clip is a reminder of what buyers really want—results, not software. Chris cuts through the noise with a message every MSP needs to hear: people don’t buy CRMs or platforms. They buy business outcomes.

Whether it’s increased revenue, better forecasting, or stronger retention, your pitch should focus on what it delivers—not what it is. The full session dives deeper into how to reframe your offers around impact. And why that shift is the key to unlocking bigger opportunities.

Turn CRM from a Cost Center into a Growth Engine

In this story-driven clip, Chris shares how one conversation changed everything—turning a simple “CRM fix” into a high-value strategic partnership. The key moment? Asking the right business question instead of just reacting to a feature request.

If your deals feel too small or narrow, it might be because you’re staying too tactical. This is a masterclass in elevating the conversation. The full session shows you how to lead discovery that builds trust and unlocks long-term potential.

MSPs Who Lead with Dynamics Win More—A Lot More

Chris delivers a data-backed reality check: MSPs that lead with Dynamics 365 generate 10x more downstream revenue than those leading with security or productivity tools.

Why? Because Dynamics opens the door to deeper advisory services, bundled offerings, and stronger customer relationships. This clip is the spark. But the full session gives you the fuel—how to reposition your value prop, use Microsoft’s internal use rights, and become a true solutions partner, not just a provider.

Don’t Plateau—Be the 10% That Captures the Opportunity

In this powerful call to action, Chris challenges MSPs to take control of their growth trajectory.

Microsoft’s data shows only a small fraction of partners will capture the massive opportunity ahead. Most will stall—held back by weak pricing, unclear offers, or reactive selling. If you’re ready to break through the plateau, this clip is your nudge. The full session is your roadmap.

These clips are just a preview—the real breakthroughs happen in the full session. Submit the form below to unlock the complete recording of Maximizing Deal Size by Selling Value and learn how top-performing MSPs are packaging, pricing, and positioning their way to bigger, better deals.

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