If your product started as a self-serve tool and later you moved upmarket to enterprise sales, how did you adjust your pricing strategy? Did you remove pricing from the website and go to custom quotes, or keep some level of transparency?

Based on the insights from our pricing strategy book, Price to Scale, the adjustment from a self-serve model to serving enterprise customers typically requires a more flexible, tailored approach:

• When your self-serve product was aimed at a broad, homogeneous audience, full pricing transparency online helped scale quickly. However, enterprise markets are often smaller, more heterogeneous (e.g., different industries like retail, pharma, or airlines), and demand tailored offers.

• As discussed in Price to Scale (see Fig. 11: Deciding on Price Transparency), many companies transitioning into the enterprise space choose to remove—or at least limit—their public pricing. This allows sales teams to craft customized quotes that extract the maximum value from each prospect, rather than forcing one-size-fits-all packages.

• Some companies may strike a balance by retaining a degree of transparency for lower-tier offerings or self-serve segments, while clearly signaling that enterprise pricing requires a direct conversation. This hybrid approach can help maintain clarity for existing customers while also allowing the flexibility needed for high-value, custom deals.

In summary, when moving upmarket from self-serve to enterprise sales, our book recommends tailoring your pricing strategy to the nature of your market—often by moving away from full public pricing towards a model that supports custom quotes and individualized value extraction.

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