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Unveiling Opportunities: The Art of Upselling in B2B Sales

Many sellers leave money on the table by not activating for upsells and expansion. Here are three tips to uncover more opportunities.

An AI-generated version of the author is pensive while sitting at a computer in a lavender field.

In the B2B sales world, we spend most of our time talking about getting more leads and closing more deals. We need those things! But there’s a massive opportunity with your customers after that first deal closes, and most teams barely scratch the surface. 

Did you know 77% of B2B revenue comes from existing customers?

Also, the top 10% of customers spend three times more money than the rest. That first deal is just the beginning.

However, you need a strategy to realize the potential of your customer relationships. Renewals are great, and the real gold is in upsells. Don’t just maintain the relationship; expand the relationship. 

If you’re like a lot of B2B sales orgs, your process looks something like this: 

  • Generic discovery or qualification call
  • Demo and negotiation focused on getting to the “decision maker.”
  • Generic onboarding and training with the CS team 

All the strategic conversations are happening at the beginning of the relationship. So, as time passes, the circle of people you’re connected with at the customer org gets smaller, leaving you with very few options at renewal time. 

You’re leaving a lot of money on the table because you’re not getting in front of more people at the company who can use your product. 

Ready for a different approach? Here are three things to build into your process at all stages to uncover more opportunities: 

1. Account Mapping 

Understand the people, process, and potential of each account.

  • People: Who do you know, and who do you want to know?
  • Process: How does the company make decisions? Who has authority and influence?
  • Potential: What are the other teams, use cases, and divisions you could serve?

2. Track Triggers

Look for changes that might affect you. 

  • Intel from your contacts: New hires, organizational changes, OKRs, new tools
  • Company news: Social posts, 10K filings, press, podcasts 
  • Product upgrades: What do your customers still need to learn you can do?
  • Usage changes: Are they using a feature way more or less than usual? More people logging in? Higher usage from some people?

3. Multithread

Multithreading is not a stage! ABNF (Always Be Making New Friends).

  • Identify who you should be talking to.
  • Make a plan: Who do you need to build a relationship with? How can you do that?
  • Offer value: What can you offer to each person? Information, resources, insights, opportunities? 

Easy, right? 

One more thing to think about — timing! We already know a few obvious times to ask for an upsell (renewal, QBRs, significant changes on the customer side, when your company introduces a new product). 

Elite sellers know that opportunities don’t just present themselves once a quarter — if you see a need, go for it. 

That being said, here are a few times you might want to hold off: 

  • When the customer has made it clear they only have a certain budget.
  • If there is a very specific/narrow use case (this is rare).
  • Right after they’ve experienced a win with your product. 
  • Before they’ve seen tangible value. 
  • When things are not going well (unless what you’re proposing will fix it).

Happy selling!