For annual plans, should we offer a discount (like two months free) as part of our strategy, or is it better to keep monthly and annual pricing at the same effective rate?

Based on the strategies outlined in our pricing strategy book, Price to Scale, there isn’t a one-size-fits-all answer—instead, it depends on your customer segments, market positioning, and overall pricing objectives. Here are some key takeaways:

• Strategic Discounting:
Our book advises that offering a discount (such as “two months free”) can be an effective tactic to secure longer-term commitment and improve revenue predictability, particularly when you’re targeting customers who value stability and are willing to commit longer. However, such discounts should come with “strings”—for example, additional commitment or tie-ins with add-ons rather than a unilateral price cut—to maintain product value and profitability.

• Customer Segmentation:
The book emphasizes the importance of segmenting your customer base. Some segments might be driven by the incentive of an upfront discount, while others may prefer consistency in pricing. A tailored approach helps in maximizing revenue capture, so aligning the annual discount with specific customer needs or behaviors can be more effective than a blanket discount.

• Maintaining Value Perception:
There is also a consideration of how discounting can impact the perceived value of your product. If annual and monthly plans have the same effective rate, the simplicity can appeal to customers who don’t want to overthink the pricing structure. On the other hand, a modest discount for annual commitment can encourage longer-term engagement without undermining the product’s inherent value—provided it’s managed carefully to avoid “price erosion” in the eyes of the market.

In summary, our book suggests that if you choose to offer an annual discount, it should be part of a broader strategy that considers customer segmentation, commitment level, and overall product value. A well-designed discount can enhance retention and revenue predictability, so long as it’s implemented with clear terms and a strategic intent.

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