If we plan to move upmarket to enterprise later on, should we design our pricing now with that future in mind, or focus on our current SMB customers and adjust as we go?

Based on the guidance shared in Price to Scale, it’s wise to design your pricing with a degree of flexibility that addresses both your current SMB customers and a potential future enterprise market. Here’s what our pricing strategy book suggests:

• Focus on your current segment: For immediate traction, particularly in the SMB or mid-market space, use approaches like the “Good-Better-Best” model, which groups features into clear packages that resonate with the segment’s needs. This approach emphasizes simplicity and fast deal velocity, which is key for growth at this stage (see Chapter 2 and Chapter 3 of Price to Scale).

• Build in flexibility for future upmarket expansion: Even if your primary focus is on SMB customers, consider a modular pricing design or flexible package architecture that can later be adapted for enterprise clients. Our book explains that while enterprise customers may eventually value a margin-maximizing model or highly tailored packages, you can start by “designing for expansion” – such as treating enterprise-readiness as a series of mini-projects within your broader pricing strategy (refer to the sections on package design and modular approaches).

In summary, Price to Scale recommends a balanced approach: prioritize the needs of your current customers while ensuring your pricing structure can be iterated or expanded as you move upmarket. This way you’ll capture immediate revenue and build the foundation for future growth into enterprise markets.