According to some embodiments, a workers' compensation insurance premium may be calculated for a workers' compensation insurance policy covering a group of employees employed by an employer. Moreover, supplemental bundled insurance premiums may be calculated for each employee to provide individual, supplemental bundled insurance policies. The supplemental bundled insurance premiums may be contingent upon the employer's agreement to pay the workers' compensation insurance premium. By way of examples, the supplemental bundled insurance policies might be associated with one or more of short term disability insurance, long term disability insurance, accidental death insurance, accidental disability insurance and/or hospital accident insurance.