The Sales Evangelist

Cross Selling, Upselling ,Drift Startup, The Sales Evangelist Podcast Today’s episode is all about the idea cross-selling and upselling to your current customers and we have Kevin Karner on the show today to give us more insights into how this can be done effectively.

Kevin works at Drift that offers live chat upgrades for new businesses where they take chats onto your website with more accessibility and as a sales tool. Kevin runs the Customer Growth department to find customers and get them on board. Kevin previously worked at HubSpot. Listen in as he offers tons of great information about the importance of cross-selling and talking to your customers.

Here are the highlights of my conversation with Kevin:

Why people do not cross-sell:

  • Not knowing how
  • Fear of doing it

Finding good customers to upgrade:

  1. Track what kind of content they’re looking at on the site.

Flag them on the CRM for follow up and engage with these users.

  1. Ask people.

Put in different calls to action inside the product. You can put it directly or through in-app engagement every once in awhile.

How you can appear more human:

  • Customer support comes from the same person every time.
  • The same person follows up with you.

Effective ways to start engaging with the customers:

  1. Get people into a trial.

Get people directly into your product.

  1. Cut down the trial time to 14 days or 7 days, for instance, and it would make people actually use it.

Scaling an upgrade without adding more people:

  1. Create a task, role, or a position focused on driving upgrades using a consultative sales approach.

Results of upselling:

10-20% increase potential every month

Focus on problem solving

Numbers are crucial but at the end of the day, it’s about solving people’s problems.

Kevin’s Major Takeaway:

Talk to your customers. Just get on the phone with prospects. What are they looking for? What do you not have that they want? How can you make it so that they would want to buy your product? Get verbal feedback.

Episode Resources:

Visit or connect with Kevin at

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The Sales Evangelist, Donald Kelly, Donald C. Kelly

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