Due to the COVID-19 pandemic necessitating social distancing, organizations and government agencies have had to resort to remote work, leading to an increased reliance on various internet-enabled software. However, this heightened dependence on cyberspace exposes these entities to a greater risk of cyber threats and crimes, potentially impacting their performance. Consequently, organizations must proactively manage their cyber risks by ensuring robust software security measures. In response to these challenges, we have developed and assessed the usability of a prototype tool known as SSRIDEX (Software Security Readiness Index tool). This tool, designed to run on mobile devices, aims to gauge the level of software security readiness among remote workers. Particularly relevant during the COVID-19 pandemic when a significant portion of the workforce is operating remotely, our SSRINDEX tool is found to be effective in measuring readiness levels. The evaluation results demonstrate that our prototype tool is capable of assessing readiness and also proves useful in assisting employees and organizations in enhancing their software security measures. © 2024 IEEE.