Avoid These 5 Common Mistakes in Upsell and Expansion Opportunities

expansion upsell mistakes to avoid

Editor’s Note: The following is a guest post from Front. Interested in contributing content to the Drift blog? Email Molly Sloan at msloan@drift.com.

Once someone has tasted your bakery’s tasty glazed donuts and coffee, they’re more likely to want to stop in for breakfast again.

That idea applies to businesses of all kinds, too — not just those selling sweet treats. It’s much easier to sell to an existing customer than a new one. While you have a 5 to 20 percent likelihood of selling to a new prospect, you’ve got a 60 to 70 percent likelihood of selling to an existing customer.

Since customer success teams have a deep understanding of customers and what they need, they’re uniquely suited to focus on upsell and expansion. But when the customer sees you as a trusted partner for support and growth, transitioning the conversation into sales can feel awkward for both of you.

Avoid these 5 upsell and expansion mistakes to make it easy for your customer success team to lead sales conversations that feel natural.

1. Divorcing commercial conversations from customer success

It’s a controversial question in the world of customer success: Should CS teams be involved in upsell and expansion conversations?

The reality is, the responsibilities of the customer success team are going to vary from company to company, so the level of selling that’s expected will vary, too. Rather than taking a set framework and applying it to your CS team, you have to look at your company’s unique customer journey and growth goals to determine what’s going to work best. Sometimes, CS will take full ownership over upsell and expansion. Other times, those conversations will be shared or fully passed to the sales team.

That said, the best CSMs are the ones with a bit of sales acumen and the best salespeople can empathize and learn the product and process of getting a customer live. If you’re here to make your customer successful, you have to be comfortable with having conversations about expansion and upsell.

2. Treating customers as numbers

Three out of four people have spent more with a company because of a history of positive experiences. But that’s tough to do when you’re saying “Hello, Ticket #40983!”

That kind of impersonal experience is why old school account management falls flat — it treated customers like numbers. It was focused on renewal and expansion from the company’s perspective, instead of thinking about it from the customer’s viewpoint, too. Traditional account management ignores the customers’ goals while being hyper-focused on personal targets.

So get to know your customers’ names, and use them often. Empathize with their company and career goals. Shift the dialogue and become more personable. It will pay dividends for your psyche and organization.

3. Assuming all customers will see the same value in the same amount of time

Whether it’s feature adoption, plan upgrade, or an increase in licenses, every team has milestones they expect customers to reach along their journey. It’s great to have these expectations set up so that your CSMs have a benchmark when they’re guiding customers. But will all of your customers fit into this timeline? Probably not.

No matter how narrowly-defined your customer base is, assuming each customer will find value in the same way in the same amount of time is antiquated.

Always remind your team that every customer is different, and while you can help them understand how expansion could help them, you can’t force them into a timeline that doesn’t make sense for their business. By keeping this top of mind when setting goals for your team, you’re setting yourself up for success.

4. Approaching the opportunity as a sure thing

“Ask questions. Don’t make assumptions.” Former Burberry CEO and SVP, Apple Retail Angela Ahrendts offered this advice on starting a new role, but her ideas apply for customer success, too. “Questions invite conversations, stimulate thinking, break down barriers, create positive energy and show your willingness to understand and learn.”

Even if the customer has something baked into their contract upon renewal or a year from now, never assume the situation has stayed the same. Continue to ask questions and confirm your contract throughout the customer journey. Then when it comes time to renew, you’re not going to be hit with a surprise, and your customers will appreciate your willingness to stay in the loop.

5. Selling a vision without being clear there are additional costs

No one appreciates a sneaky upsell. When your customer agrees to a new service or feature, they should always understand what it will cost.

Similar to over promising on the  product side, avoid promising something from a higher priced plan when you know the customer will be moving forward with a lower tier that doesn’t include those features. Instead, use that as an upsell opportunity later on in the sales process.

Before a customer even reaches the CS team, they should have a solid understanding of how your business works. This means having a strong and transparent relationship with your sales team.

  • What does the customer success process look like?
  • Who do I speak to, how often, and when do I use success vs support?
  • Do you have a freemium model, and/or tiered pricing? Add-ons?

You can use this Sales to Customer Success Introduction Checklist for more information to gather when you’re transitioning customers from sales to CS.

The bottom line is, being transparent about additional costs will help you gain the trust of your customer, which always pays off in the long run.

Thinking of upsell and expansion from the customer perspective

Upsell and expansion are growth opportunities for both you and your customers — but keep the focus on your customers. This will foster a culture of humility on your CS team. Encourage CSMs to ask themselves, “Will this help the customer grow? Will this make it easier for them to get work done? Will this add more value than they’re already receiving?”

With the customer’s viewpoint in mind, CS becomes a trusted partner, not a pesky email or a pushy sales call that customers dread answering.

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