How do you develop a value proposition for a startup that has two offerings that serve two unique customer segments?

This depends on how different your two offerings are! Ideally, you want a corporate value prop that speaks to the core value of your product portfolio as a whole, and then you want to tailor that for different audiences.

One of the best ways of doing that is by being clear on your core use cases and then creating different flavors of your use cases for each of your segments. For instance, Quickbase’s core value prop is our ability to help companies see, connect, and control complex work. Our top use cases are project management, resource management, process orchestration, etc. That remains true across any segment… but for construction that work might have a different meaning and language compared to healthcare for instance.

The way you position this to an SMB will slightly differ from the way you position it to an Enterprise company, but the core problem and use cases you solve for should remain consistent.

TLDR; create core use cases and a value prop that remains consistent, and tailor that slightly to each audience.