Systems and methods for machine learning and adaptive optimization are provided herein. A method includes continually receiving input that is indicative of client events, including client behaviors and respective outcomes of software trials of a product maintained in a database, continually segmenting open opportunities using the client behaviors and respective outcomes, continually scoring and prioritizing the open opportunities using the client behaviors and respective outcomes for targeting and re-targeting, continually adjusting targeted proposals to open opportunities and sourcing in prospects based on a targeting scheme, continually presenting targeted offers to create expansion opportunities and updating a product roadmap of the product using the open opportunities, the product roadmap including technical specifications for the product.
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