Upsell conversations that don't feel pushy

We have covered how to defend a renewal and how to put through a price increase in articles of their own. This is the third conversation with an existing customer, the one about more, and the one reps most often put off until the customer gets in touch first. The figures usually wheeled out to justify the call concern how much more a new customer costs to win than an existing one costs to keep, and how much likelier a sale to an existing customer is than to a new one. Neither claim has a traceable primary source, so we do not use them. What can be verified is plenty.

The numbers that hold up

The 2016 Pacific Crest SaaS survey, covering 336 companies, measured what a dollar of new annual contract value cost to win: a median 1.13 dollars from a new customer, 0.27 dollars from upsells, 0.20 dollars from expansion of existing plans and 0.13 dollars from renewals. Paddle's benchmark data from ProfitWell shows why that matters for growth: companies with a lifetime value to acquisition cost ratio of 3 to 5 drew a median of just under 20 percent of revenue from expansion, and the top 40 percent of growth companies at least around 20 percent and as much as 40 percent. HubSpot's survey of sales professionals has 91 percent of them upselling, with upsells bringing in an average of 21 percent of company revenue. So upselling is not a bonus. It is a quarter of the revenue at a quarter of the cost.

What the research says about tone

Corporate Visions ran a test in 2018 with Nick Lee of Warwick Business School and 426 participants to find out which message works best when upselling existing customers. A pure 'why change' message, the kind you would use on a new customer, lost. A pure 'why stay' message lost as well. The winner was a hybrid: first confirm why the customer's earlier decision was right, then show what has changed and why the next step follows from it. The same company's earlier studies, in 2016 with Stanford's Zakary Tormala and in 2017 with Lee, found that a provocative message aimed at existing customers lowered renewal intentions. The Swedish norm of long-term customer care says the same thing without the statistics: pressure a happy customer and you lose the relationship, and the relationship was the whole point.

Four moments to wait for

Upselling is a matter of timing, not pitching. Gainsight's customer health model lists the signals to watch: how many people use the product relative to the licences held, whether the features actually get used, whether the customer turns up to review meetings and does what was agreed, whether there is an executive sponsor, and whether the customer can point to business results. Four moments fall out of those signals.

1. Usage hits the ceiling: the customer is using 90 percent of its licences, or another department asks for access. The conversation is about not putting the brakes on something that works.
2. A result the customer has mentioned: 'we saved two days per quote' is the opening for the question 'where are the next two days?'.
3. A change on the customer's side: a new manager, a new company in the group, a new market. The old contract was sized for the old company.
4. Three months before a renewal window: the expansion is folded into a renewal that has to be negotiated anyway, rather than becoming a separate decision.

The conversation in four steps

Results first: 'When we started in March the goal was to shorten quote time. You are now at four days, down from nine. Does that match how it feels on your side?' The customer confirms, or corrects, and either way the conversation starts in the customer's reality. The next problem: 'What takes time now, when the quote does not?' This is where the upsell surfaces on its own, if there is one. The third step is the link: 'What you are describing is what the add-on module solves for three of our other customers in your industry. Do you want me to show you how, or is the timing wrong?' The timing question is not politeness, it is what stops the customer from feeling sold to. The fourth step is a next step with a date, as in any deal.

Missing from the structure, on purpose: the price list, the word 'upgrade' and a discount that runs out on Friday. The Corporate Visions hybrid depends on the customer first being told their old decision was right. A discount deadline says the opposite: the old decision was too small, and the customer needs correcting, fast.

The Swedish tone

In Swedish, the line between customer care and selling is thinner than in American scripts. 'I'm calling to see how it's going' is customer care. 'I'm calling because I saw you are hitting the ceiling and wanted to ask whether it is slowing you down' is customer care with a question attached. 'I'm calling to offer you an upgrade' is selling, and the customer hears the difference in the first sentence. Stick to the first two and let the customer be the one who asks for more.

What makes the conversation hard to practise in real life is that each customer only gives you one shot, with a three-month wait until the next. In Salesprep's Follow-up module you describe the context, for instance a happy customer hitting the licence ceiling three months before renewal, and practise the call against an AI buyer who is satisfied but on a tight budget. Every call is scored on seven metrics with a written comment per score. Follow-up is available on Pro and up, and three free calls in the Cold call module come with the account, no card required.