ABSTRACT Objectives: to validate the content and usability of the Retire with Health web software. Methods: a methodological study. The content validation was carried out by seven experts in the aging subject, using an instrument that evaluated the objectives, contents, relevance, and the environment of the web software. Usability was validated by seven experts in software development, referring to ergonomics, functionality, usability, and efficiency. The data were submitted to statistical analysis, described by calculating the Content Validity Index. Results: the global Content Validity Index found 0.97 for the usability aspects and 1.00 for the content. After incorporating all the experts’ suggestions, the Retire with Health web software was made available on the internet (www.aposentarsecomsaude.com.br). Conclusions: content validation and usability showed that the web software meets the objective of supporting reflection on retirement, with a high level of agreement among experts.