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Dear Abby Hammer: When Are Customers Ready for an Upsell

By Abby Hammer posted 01-14-2021 12:33 PM



Dear Abby Hammer,

My company is less experienced when it comes to driving expansion sales. Our CSMs sometimes feel timid asking customers for money. That said, we know that in order to grow, Customer Success (and expansion selling!) is key.

We worry about striking a balance between fostering and encouraging upsells to increase sales, and risking hurting a customer relationship by unnecessarily pushing investments.

How can I tell my team that now is the right timing for expansions? How can I get my team more comfortable with selling?

 -Striking a Balance Between Success and Selling


Dear Striking a Balance Between Success and Selling,

It’s not surprising to hear your team is cautious when it comes to expansion opportunities. For those of us without a Sales background, it can be uncomfortable to ask for money! As Customer Success is all about driving customer value, it’s reasonable that some team members feel conflicted.

As you stated, expansion selling as a function of CS is a key element to corporate growth. As your business grows, more revenue will be generated from your existing customers. This really plays into the essence of what CS is about.

Check out these notes on how to identify a customer that’s ripe for an upsell as well as how CSMs can become more comfortable with selling.

When Should Customers be Approached for Expansion Sales?

Customer Success teams should take a consultive approach to expansion sales. You should look at both upsells and cross-sells as an extension of the value your team provides everyday. Ask yourself – how does this tool of expansion sales fit into my client’s end goals?

When trying to determine if a customer should be approached for an expansion opportunity, consider the following points:

  • Which product plan is your customer currently using?
    • Are they close to outgrowing their current solution (licenses, etc.)? Are they potentially missing out on key features they could be accessing at other product levels.
  • Why did they originally invest?
    • Why did the customer originally invest in your solution? Do metrics indicate they have met their goals? Or do they need extra help?
  • Upcoming Projects or Initiatives?
    • Does the customer have any major upcoming projects or initiatives? Could specific product add-ons or investments help them meet these goals?
  • Who else can we help?
    • Could other teams within our customer organization find value in our tool?

By asking yourself these questions, you should be able to determine which customers are best positioned for an upsell or cross-sell. Above all avoid pitching customers who won’t see additional value. While  you may get a sale in the short-term, you’ll risk damaging your long-term relationship as a trusted advisor.

Getting CSMs Comfortable with Selling

One of my favorite parts about working in CS is seeing the types of backgrounds that excel in the role. Oftentimes some of the best CSMs come from non-customer facing career paths. The downside however is that not all CSMs come from a strong sales background.

When getting your Customer Success team comfortable with expansion sells, remember the following:

1. (Worthy) Expansion Sales play into the goal of CS – delivering ongoing customer value

  • Use the above criteria to ensure you are serving the right upsell/crossell opportunities to the right customers.
  • By determining your offering adds value and helps your customer reach their goals, you’ll avoid pushing un-helpful add-ons that can damage your relationship as a trusted advisor.

2. As a CSM, you are in tune with customer needs and wants

  • Unlike sales teams, CSMs are along with their accounts each step of the way. You see your clients grow and evolve into your product. You understand their goals and reason for investment. This provides excellent visibility into what expansion opportunities will deliver value.

3. Above all else, you’re a trusted advisor

  • When problems arise, your customer seeks you out as their trusted advisor. They look to you for support and advice each step along their customer journey. Since their success is at the heart of what you do this advice shouldn’t just be reactionary. If a particular tool or add on would help the customer reach their goals, you as their CSM should suggest what investments will help them.

I hope these points bring your team comfort as tackle expansion sale opportunities. By asking these questions and understanding your role as a trusted advisor, you should feel confident in engaging customers for upsell opportunities.

-Abby Hammer