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.
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Most sales are lost to inertia, not rejection. Implement a specific, escalating follow-up sequence (30 mins, 60 mins, next day) after sending an offer. This disciplined approach isn't pushy; it helps busy prospects make a decision while their interest is at its peak.
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.
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.
Don't just solve the problem a customer tells you about. Research their public strategic objectives for the year and identify where they are failing. Frame your solution as the critical tool to close that specific, high-level performance gap, creating urgency and executive buy-in.
The moment a customer buys, they signal maximum trust. This is the optimal time for a salesperson to be assertive with upsells, cross-sells, or referral requests. Many reps mistakenly push too hard at the beginning of the sale when trust has not yet been established.
Don't pitch features. The salesperson's role is to use questions to widen the gap between a prospect's current painful reality and their aspirational future. The tension created in this 'buying zone' is what motivates a purchase, not a list of your product's capabilities.
Move beyond selling products or solutions. The highest level of selling is articulating the customer's problem so well, and expanding on its implications, that they see you as the only one who truly understands and can solve it.
Contrary to the 'value first, pitch last' model, present the full offer before your launch event even begins. Then, create urgency by offering a new, valuable bonus each day that expires within 24 hours. This strategy leverages peak attendance on day one and frames the purchase as an opportunity to gain extra value rather than a hard sell.
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.
Deals are lost when salespeople fail to spend enough time in discovery to understand the customer's true need. They must identify the 'moment of demand'—when the customer both recognizes their problem and is ready to decide—rather than rushing to the close with the wrong solution.