Strain engineering offers unique control to manipulate the electronic band structure of two-dimensional materials (2DMs) resulting in an effective and continuous tuning of the physical properties. Ad-hoc straining 2D materials has demonstrated novel devices including efficient photodetectors at telecommunication frequencies, enhanced-mobility transistors, and on-chip single photon source, for example. However, in order to gain insights into the underlying mechanism required to enhance the performance of the next-generation devices with strain(op)tronics, it is imperative to understand the nano- and microscopic properties as a function of a strong non-homogeneous strain. Here, we study the strain-induced variation of local conductivity of a few-layer transition-metal-dichalcogenide using a conductive atomic force microscopy. We report a novel strain characterization technique by capturing the electrical conductivity variations induced by local strain originating from surface topography at the nanoscale, which allows overcoming limitations of existing optical spectroscopy techniques. We show that the conductivity variations parallel the strain deviations across the geometry predicted by molecular dynamics simulation. These results substantiate a variation of the effective mass and surface charge density by .026 me/% and .03e/% of uniaxial strain, respectively. Furthermore, we show and quantify how a gradual reduction of the conduction band minima as a function of tensile strain explains the observed reduced effective Schottky barrier height. Such spatially-textured electronic behavior via surface topography induced strain variations in atomistic-layered materials at the nanoscale opens up new opportunities to control fundamental material properties and offers a myriad of design and functional device possibilities for electronics, nanophotonics, flextronics, or smart cloths.