Computer-based systems and methods are described for generating personalized, automated contribution strategies for scheduling contributions to a retirement savings plan or other savings plan. Embodiments of the systems and methods provide visual and other educational displays to assist a client in choosing a suitable savings contribution strategy that may take into account at least one of the set consisting of: details of an employer-sponsored savings fund available to the client which may include opportunities for employer matching-funds, acceptable portion of standard-of-living increases derived from salary raises that the client is willing to contribute to a savings plan, client's current savings behavior and value of savings portfolio, effects of the stochastic nature of future investment portfolio value, and changing federal tax regulations. Clients may use the systems for educational and planning purposes and/or may authorize automated triggering of contributions with scheduled increases and/or decreases as specified by the selected plan.