Palm oil has been one of the major renewable sources for the production of energy, food, and chemicals. Despite the huge demand and production rate, the majority of the stakeholders consist of small and medium enterprise company, especially at the plantation site. Due to this, revolution of industry 4.0 in palm oil industry, especially the upstream process is a very challenging issue. Stakeholders are reluctant to move toward the new technology due to the lack of understanding of the potential features and advantages, as well as hesitate to invest in new technology. This paper proposed a novel mathematical model to evaluate potential Industry Revolution 4.0 features based on existing technologies and optimised implementation strategy for each stakeholder. Each potential feature was evaluated based on its potential impact, estimated investment cost and non-implement penalty cost. The model covers a long-term operation to consider the inflation rate and dynamic maturity of each feature. A case study focusing on cybersecurity features is discussed and the result shows that only 7 out of 16 features that are feasible to implement in oil palm industry, where blockchain and smart contract are the most promising features to be implemented. All the features are recommended to be implemented at a later stage due to the increasing maturity of the Industry 4.0 technologies and cheaper cost.