13 Tips for Upsells

When it comes to upsells, timing is everything. Knowing when to present an offer to a customer is just as important as knowing what offer to present. Here are 13 things you need to know about making an upsell offer to a customer.

1. Be Clear on What Success Means

You must know what “success” means to the customer in the context of what your product offers, not just at a high-level, but at every phase of the customer lifecycle.

2. Set Goals with Your Customers

Set goals with each customer and come to an agreement on their specific success measurements. If you know their goals, then you know if they are on their way to reaching those goals.

3. Benchmark Where Your Customers Start

Refer back to the benchmark statistics to show customers where they are at relative to where they were and to show them how they are progressing. If a customer is not progressing fast enough toward their stated goals, it may be time to escalate the issue internally.

4. Identify Success Milestones

Use success milestones (like adding capacity, using new add-ons, or buying more seats) to ensure that your customer is on their way to achieving their goals while being successful with your product. Not every milestone will be an upsell opportunity, but some will, and leveraging the relationship between success and upsell will enable you to make offers at the right time for the customer.

5. Ask for the Sale

The number one reason upsells fail to occur is that the vendor fails to ask for them! Since you’ve combined an upsell cadence with your customer’s success milestones, upsell conversations should be non-events that happen without much pushback, resistance or negotiation.


6. Identify Successful and Happy Customers

To ensure you are selling to an audience that’s the most likely to buy, talk to customers that have positive health scores. Conversely, avoid contacting customers with an upsell opportunity if they have a below average health score.

7. Identify Your Most Profitable Customers

If you can identify shared characteristics between your most profitable customers to date (or in some specific time frame, maybe the last 18 months), then you can use those characteristics to identify the existing customers that are the most likely to be profitable in the future. Kick start those customer accounts with an upsell opportunity.

8. Identify Customers with Expansion Potential

Once you’ve identified the shared characteristics among the customers with greater product use, you can use those characteristics to find other existing customers who are more likely to react positively to an upsell opportunity. You can massively improve your chances by targeting customers that look like those who’ve expanded use in the past.

9. Improve Time to First Value & Upsell Faster

The faster you get a customer achieving value – the faster they move through their success milestones – the quicker and more often a congruent upsell opportunity can be presented to them. And, more upsell opportunities in a shorter timeframe will drive up Customer Lifetime Value (CLTV).

10. Mention Upsell Early in Their Lifecycle

Start mentioning upsells early in the customer’s lifecycle and leverage the connection with the salesperson and product marketing. Draw attention to your product’s functionality, features, or adjacent products in the context of their success.

11. Enable Self-Service Where Possible

Even in a high-touch, enterprise sales environment, it can be effective and easy to enable self-service for certain things that do not require human intervention. If you want to make upsells happen seamlessly and without friction, surface them at the right time based on “success milestones,” allow self-service provisioning, and watch your CLTV grow.

12. Use Self-Service Trials and POCs

If a customer achieves a “success milestone” and the upsell opportunity you surface for them is a new module, let the customer provision the new module using either a self-service free trial or a longer-term proof of concept. There may be a way to incorporate self-service with upsell opportunities even if the actual “sale” occurs later in a high-touch situation.

13. Offer Concierge Onboarding

Roll the concierge onboarding cost into the upsell cost; they may be will to pay a professional services fee to make this happen. Alternatively, you may be better off rolling the cost in the cost to serve, knowing that getting them onboard with this new functionality won’t just add new revenue, it will also keep your customers around even longer, growing CLTV.

Learn more at Gainsight.

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