Abstract: A method is provided for optimizing healthcare and retirement benefits for an employee. The method includes receiving information about at least one medical insurance plan and at least one retirement savings account for which the employee is eligible and selecting for the employee a medical insurance plan from the at least one medical insurance plan. The method also includes determining a first amount for the employee to contribute on a pre-tax basis to at least one health care savings account. The first amount is at least equal to an estimated total of eligible expenses not covered by the medical insurance plan. The method further includes determining a second amount for the employee to contribute to the at least one retirement savings account. Selection of the medical insurance plan, the first amount and the second amount optimize the healthcare and retirement benefits for the employee.