This paper explains the first steps of a smart PSS engineering approach, aimed at eliciting stakeholder needs, prototyping the value proposition, representing how the Original Equipment Manufacturer (OEM) will capture value and share it with a collaborative network of stakeholders while identifying and prioritizing risks from the value proposition. The approach addresses two gaps in the field of smart PSS design: (i) the need of visualizing solutions to support the transformation of value propositions for the stakeholders into a contract mechanism supporting value capture by the offering company and (ii) the importance of integrating risk management during the design of Smart PSS value proposition