In this article, I consider individual aspects of the economic security of Saint Petersburg and the Leningrad Region amid the geo-economic uncertainty observed since 2014. The object of the study is the economic and technological sustainnability of Saint Petersburg and the Leningrad Region given geo-economic risks and growing challenges to economic security. To evaluate the economic security of Saint Petersburg and the Leningrad Region, I employ some of the parameters proposed in the Strategy for the Economic Security of the Russian Federation until 2030. I also use other parameters pertinent to the evaluation of the state of an economy amid geoeconomic uncertainty, in this case, in the conditions of the crisis of 2014-2016, brought about by both external and internal factors. I employ the concept of the triad of regional economic competitiveness, regional economic security, and sustainable regional socio-economic development. I believe that this triad does not only demonstrate the logic of the current and prospective development of a Russian region but also highlights weaknesses and opportunities for future development. The competitiveness of Saint Petersburg and the Leningrad region amid geo-economic uncertainty is considered through the performance of the regions' key enterprises and emerging technology companies. I analyse the revenue profiles of the regions' leading industrial enterprises in 2014-2015 and emphasise the role of key industrial exporters. This article is a preliminary study without any claim to completeness. Further research will seek to present the findings obtained in more detail.