Your guide to sales enablement for upselling 

Estimated reading time
4 minutes
1st December 2020
Author: Natasha Keary
Posted in: Sales

If you’re like most businesses out there, your sales enablement material aims to help your teams do two things: 

  1. Increase win rates for potential deals 
  2. Boost account acquisition  

According to the latest CSO Insights Report, these were the two most common sales enablement goals across companies last year. However, it turns out that new deals and accounts only makeup 20-30% of the average company’s annual revenue. The remaining 70-80% comes from somewhere much closer to home: your existing customer base. 

Upselling and customer expansion are vital sales opportunities that account for a large proportion of company revenue. But creating sales enablement for upselling and expansion isn’t merely a case of repurposing acquisition materials. Instead, upselling resources need to address a different set of scenarios. Let’s look at the four questions you need to answer to build a winning sales enablement strategy for upselling and growth. 

woman texting and using a laptop outside in the city.

1. What has your customer already gained from your solution? 

Everyone is under pressure to prove ROI. Your customer is probably tasked with proving ROI across various functions, businesses, and solutions at once. Providing materials that showcase your solution’s value saves them from doing the legwork and is the first step to securing a renewal or upsell. 

Your ROI reminder could be in the form of a regular progress report. It could be a monthly check-in email from a member of your team or a simple ‘here’s what you did last week’ digest. The important thing is to remind your customer of your solution’s consistent value and provide a tangible way of proving ROI to the wider business. 

The secret to this resource material – as with all sales enablement material – is making your content as personal as possible. This isn’t an excuse to repurpose your generic sales resources but to showcase your understanding of the customer’s specific use case. Is there a particular business goal they’ve achieved with the help of your solution? How does your offering align with their business objectives? 

Materials that invite customers to engage with your solution more thoroughly can also help here. Regular comms, webinars, and product guides remind your customers to utilize your solution’s full offering. Ultimately, the more engaged with your solution your customers are, the more value they can derive from it. 

woman working on laptop

2. What more can your customer gain from your solution?

You’ve identified the ways your customer is using your solution; now spot the gaps. Are there ways that your solution could fill a hole in operations or streamline a notoriously lengthy process?

Your sales enablement for upselling should also consider the wider business: are there other departments in your customer’s organization that would benefit from your solution? Could using your solution business-wide result in a more consistent workflow? 

Marketing materials like case studies and reviews are valuable here. Showing a customer how a similar company upgraded and reaped the benefits is the easiest way to provide social proof – and supply reason for significant FOMO. 

You’ll want to arm Customer Success with these resources, and give your team support and training on upselling in the right way. Unlike acquisition, sales enablement for upselling builds on existing relationships you have with a customer, so it’s important to keep those relationships productive and trusting. 

people in meeting

3. Why should your customer stick with you?

The largest difference between acquisition and upselling? This time you don’t have to contend with status quo bias.

Status quo bias is what makes us humans want to stick with what’s familiar and comfortable. This is a rational-emotional response that makes selling a new solution to a prospect a real challenge. If a potential customer feels comfortable with their current solutions, convincing them to try something new requires more than rationality. 

Your sales enablement for upselling should emphasize that you’re already the status quo. Time is tight for most of us – and finding, implementing, and learning a new solution is costly on this front. There are also associated risks with trying out a different offering – regret and blame are at the forefront of our minds when we even consider a new approach. Your materials should prioritize the fact that you’re a trusty and reliable company who have already built up a relationship with your customer – and you’ll stay the same in the future.

Naturally, there are occasions where mistakes happen, and a good approach (and apology) should be part of your sales enablement for upselling kit. Which leads to…

4. What happens if your customer wants to leave? 

A customer wanting to end their contract isn’t – and shouldn’t be – a reason to bring back out your sales pitch deck. But equipping your Customer Success and Support teams with resources for this scenario can help steer the conversation towards solutions instead of terminations.

A good response to ‘I don’t want to renew my contract’ is a persuasive set of comms and evidence of the potential value ahead. A great response to ‘I don’t want to renew my contract’ is an empathetic and persuasive set of comms, and a personalized summary of what you’ve already achieved, and could go on to achieve, together. 

As with apologies, your responses to customer dissatisfaction should be honest, direct, and responsible. If in doubt, don’t forget that a better term for sales enablement is ‘customer enablement’ – if your materials aren’t consistently focused on better solutions for your customers, think again.

Want to make sure your sales enablement content strategy is in good shape for the year ahead? Check out our handy guide below:

Content strategy for sales enablement cover page

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