It’s a classic marketing debate: do you push an upsell at the ‘perfect’ moment, even if the offer is just okay, or hold off for a truly compelling offer? For Australian SMEs, we believe offer quality consistently trumps timing, though smart timing certainly amplifies results. Focusing solely on when to ask ignores the fundamental principle of delivering genuine value.

Think about your own experiences as a customer. Have you ever been aggressively upsold something you didn’t need, or that wasn’t a clear improvement on your initial purchase? It feels frustrating, right? That’s because timing without relevance creates a negative experience. A fantastic offer, presented at a slightly less-than-ideal moment, is far more likely to convert because it’s inherently appealing.

Here’s what we’ve observed with our clients:

• Value perception is key: Upsells need to feel like a logical extension or enhancement of the original purchase. A premium version with added features, a complementary product that solves a related problem, or extended support are all examples.
• Customer journey mapping matters: While not strictly ‘timing’, understanding *where* a customer is in their journey informs offer relevance. Someone just making their first purchase needs a different upsell than a long-term, loyal customer.
• Segmentation unlocks potential: Don’t treat all customers the same. Tailor upsells based on purchase history, demographics, or behaviour. A customer buying camping gear might appreciate an offer on hiking boots, while someone buying office supplies won’t.
• Post-purchase is prime time: Immediately after a purchase, customers are already in a ‘yes’ mindset. This is an ideal window, but *only* if the offer is genuinely valuable.

That said, ignoring timing completely is a mistake. We recommend A/B testing different presentation times – immediately after purchase, a few days later via email, or even triggered by specific website behaviour. However, always prioritise a strong, relevant offer. A 10% discount on a truly useful product will outperform a 20% discount on something the customer doesn’t want, regardless of when you present it.

Ultimately, successful upselling is about building value and trust. Start by refining your offers to ensure they’re genuinely beneficial to your customers, then optimise the timing to maximise impact. If you’re unsure where to start, a thorough review of your customer journey and current upsell strategy is a great first step.