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To uncover upsell opportunities, use the "Apologist Pitch." Approach existing customers and say, "Our bad, we've done a poor job communicating everything we offer." This reframes a sales pitch as a helpful service, making customers receptive and often leading to immediate deals without aggressive selling.
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Don't wait for a formal QBR to discuss expansion. The immediate post-sale period is a golden window for additional sales. The customer's excitement and trust are at their peak. With their most urgent need solved, they are highly receptive to addressing other business challenges.
When a customer expresses dissatisfaction or feels they need more support, position a higher-tier service as the specific solution to their problem. This turns a potential churn risk into a revenue expansion event.
Sell an initial package with a guaranteed outcome. Mid-delivery, celebrate the customer's success and reframe it as completing only "Phase 1" of a larger mastery journey. This positions the upsell not as a new sale, but as the logical continuation of their initial successful commitment.
A blanket price increase is a mistake. Instead, segment your customers. For those deriving high value, use the increase as a trigger for an upsell conversation to a better product. For price-sensitive customers, consider deferring the hike while you work to better demonstrate your value.
To increase average deal size, introduce a new, much higher-priced package (e.g., $100k) and pitch it as your primary offer. Commit to selling it hard. For clients who object, you can then downsell to your original core offer (now priced at $35k), which appears incredibly reasonable by comparison. This captures whales and boosts conversions on your main offer.
Don't wait for customers to ask about your value. Assume they view you and your competitors as commodities. It's your job to proactively explain why you're different and what additional value they receive for your price, effectively telling 'the rest of the story' beyond the basic product features.
Most people mistakenly try to upsell after a customer has received value. The correct timing is when their need is at its peak. You sell two steaks when the customer is starving, not after they've finished the first one, by amplifying their perceived lack before they've had their first bite.
Gage Donovan increased his sales opportunities from 10% to 90% by changing his pitch from asking "Can I wash your windshield?" to stating "As a courtesy, we're washing everybody's windshields." This removes the customer's feeling of obligation and positions the offer as a given value, leading to higher acceptance.
When a customer buys, they implicitly trust you to offer other relevant solutions. If they discover a helpful product you never mentioned, you've broken that trust, causing lasting damage that's more significant than the missed revenue.
Acquiring net new customers is expensive and resource-intensive. A more efficient growth strategy is to focus on expanding business within your existing customer base, treating these upsell and cross-sell opportunities with the same strategic importance as new logo acquisition.
