AI Coach: find and fix deal issues before they result in closed-lost using AI


Upsell Strategies: When Should You Upsell?

4 min
Average Score

Alexander Berman

Founder of

Watch Session

In this comprehensive session, we will explore the art of upselling and how sales representatives can leverage this technique to boost their revenue. Upselling to current customers can be a game-changer for sales professionals, and we'll provide you with valuable insights on when and how to upsell effectively. 

Upselling to your existing customer base can be the quickest route to increased revenue. Customers who have already made a purchase from you trust your brand, making them more likely to make additional purchases. Alex Berman, an experienced sales strategist, shares a success story where one client generated $100,000 through upselling to their current customers.

What is the best time to Upsell

Knowing when to upsell is vital. If your company has failed to deliver on a previous promise, it's essential to rectify the situation before considering an upsell. Upselling should only occur when the client is satisfied with your service. Three key periods of maximum hype for upselling include:


   - Right before a deal is signed.

   - Immediately after a deal is signed.

   - You can find out the third moment in the video session

Identifying these moments of heightened enthusiasm in your client can significantly increase your chances of a successful upsell. To make a compelling upsell pitch, follow these steps:

Step 1: Summarize Achievements

   Start by summarizing the successes you've achieved together. For instance, you might say, "We're really excelling with the Anderson project."

Step 2: Lean into Excitement

   Gauge their excitement and agreement with your accomplishments. If they acknowledge your success, it's a positive sign that they're receptive to an upsell.

Step 3 and 4: Find Out in the Video!

By following this approach, you can seamlessly guide your client towards an upsell opportunity.

Upselling is a powerful tool in a sales rep's arsenal, offering a quick and efficient way to increase revenue. By understanding the right timing, crafting persuasive pitches, and identifying moments of maximum client enthusiasm, you can become a master at upselling.

For an in-depth exploration of these upselling strategies and additional insights from top agency salespeople, watch Alex Berman's session. Discover the multi-million dollar secrets that can help you crush your sales quota. Start your journey towards becoming a top-performing sales representative today.

If you want to learn more about upselling skills, watch this other session.

How Triple Session works

Training, Testing, & Feedback

Triple Session's proven formula accelerates your sales performance through consistent, organized practice, backed by measurable results.

Watch a session

Bite-Sized Knowledge

Our expert-led video sessions simplify complex sales concepts into easy-to-digest 5-15 minute videos for better retention.

Test your understanding

Test Your Understanding

After each session, there will be a quiz to test your understanding and help you improve on any areas that need more attention.

Evaluate and Grow

Evaluate and Grow

Get progress snapshots after each quiz to track your improvements and achieve your sales mastery goals.