How do I run an upsell conversation without sounding like I am shaking them down?
Earn it first. If you cannot show the customer a result they got in the last quarter, you have not bought the right to ask for more money, and they can feel that. When you can, frame the upsell as the next problem rather than the next tier: here is what you achieved, here is the thing blocking you from doing it for the rest of the team, here is what that costs. Bring the new stakeholder into the conversation early instead of asking your champion to sell internally alone. And be willing to say not yet, because one badly timed ask costs you more than the deal was worth.
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5 resources, 5 link-checked.
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A seven-step method for building relationships beyond one contact. It is written for new deals but the mechanics are identical for protecting and expanding a renewal.
Nine chapters covering the QBR structure, the common mistakes (generic content, dwelling on the negative) and how to keep quality when you have too many customers for one per account.
McKinsey found B2B customers with strong executive engagement are 2.5 times more likely to renew.
87 percent of business buyers want their rep to act as a trusted advisor, not a vendor.
Keep a QBR under an hour, and lead with outcomes rather than a data dump (72 percent of senior decision-makers say information overload delays decisions).
The Gainsight CEO on why CS should own an NDR number rather than just a churn number, including the idea of giving every CSM their own book of MRR to grow from 100 to 115.
The cleanest definition of expansion MRR with the formula and the benchmark that matters: top companies get up to 40 percent of new ARR from existing customers.
It takes the exact fear in this question seriously, that asking for more money makes you sound like you are shaking the customer down, and gives language that keeps the conversation about their outcome.
