In this chapter, we examine strategic technology management through the lens of the Quintuple Innovation Helix plus AI (QIH + AI) and the prospective retrospective methodology. We show the validity and relevance of this methodology amid various dynamic socio-economic, socio-political, and socio-technical transformations, including digitalization, and the circular economy, alongside the growing multipolarity in geopolitical, geo-economic, and geo-technological contexts. We propose the QIH + AI methodology as a powerful tool for strategic technology road mapping, particularly in times of transformation and complexity.