This paper describes the design, development, calibration and validation of a novel soil–structure contact stress sensor. The new sensor design combines a novel operating principle, fibre Bragg grating (FBG) strain sensing and data-driven mapping techniques to create a multi-axis contact stress sensor that is both economical and suitably robust for deployment in underground construction applications. The instrumentation process is informed using a ‘virtual twin’ of the sensor in which synthetic data is generated by extracting and interpolating virtual FBG strains obtained from a large number of 3D finite-element calculations. A physical prototype is subsequently developed to demonstrate proof of concept. Results from laboratory validation tests give confidence in the sensor's ability to provide accurate contact stress measurements in typical soil–structure interface shear applications. In particular, the novel sensor structure and operating principle was shown to achieve excellent measurement of effective normal stress. The new sensor design harnesses many of the inherent benefits of FBGs including immunity to electromagnetic noise and water ingress, and the use a single lightweight cable and connector, which significantly simplifies installation on site compared to electrical multi-axis sensors.