Objective – to develop and test an integral Digital Maturity Index (DMI) and a “readiness × expected yield” map to prioritize phased implementations. Methods – mixed design: a proxy survey of 50 farms, construction of a five-block DMI (A-connectivity, B-data/accounting, C-processes/automation, D-competencies/organization, E-integration/effects), non-parametric comparisons, and correlation analysis were applied during primary data collection on economic entities under conditions of official statistics deficiency, to reduce heterogeneous indicators into a single comparable assessment of digital competence, identify differences between agricultural business entities by scale and profile, and establish the strength of the connection of individual factors with the final index. Results – heterogeneity in the technological readiness of agricultural enterprises was recorded: infrastructure block A is above the threshold, while blocks B and C, namely data and processes, remain bottlenecks. Enterprise size is positively associated with the DMI, but management practice partially compensates for the scaling effect in small and medium-sized agribusinesses. The priority map highlights “quick wins”: cost accounting, warehouse and inventory, logistics, electronic veterinary and phytosanitary processes, field journals with meteorological data, and, for levels not lower than “medium,” vehicle fleet telemetry and sales analytics. Conclusions – the proposed methodology creates a foundation for 12–18 month management roadmaps and sectoral policy toward enabling information systems to exchange data for coordinated operation. The results can be used in developing regional programs to support AIC digitalization, especially for small and medium-sized agricultural enterprises.