This cross-sectional study was part of a comprehensive workplace health promotion program (WHPP) implemented in the work environment of small- and medium-sized enterprises (SMEs) in Western Slovenia, which included web-based educational campaigns aimed at promoting positive lifestyle changes among workers, including healthy eating habits and physical activity. As part of this program, which included campaigns in the areas of stress management, ergonomics, sleep hygiene, communication, work climate, and absenteeism, we developed and examined the engagement frequency in web-based content on healthy eating and physical activity for the companies included in the WHPP. This part of the project lasted from 2020 to 2022. Prior to the educational campaign, participants voluntarily completed a screening questionnaire. We analyzed the patterns of 370 workers in terms of their job classification (predominantly sedentary, predominantly standing, or predominantly physical), body mass index (BMI), gender, age, and selected indicators of diet and physical activity. Of the 88 companies participating in the WHPP, 26 took part in our web-based educational campaigns on nutrition and physical activity. Through an empirical analysis using descriptive and inferential statistics and a linear regression, we found that, on average, the engagement frequency (i.e., proportion of educational personal e-mails read) was highest among men with sedentary work, with older employees participating more actively than expected. Moreover, workers with good dietary habits and a favorable BMI proved to be the most avid readers of the web-based campaigns. Despite the overall low participant engagement frequency, it is clear that web-based educational campaigns are more appealing to workers with sedentary jobs and good dietary habits. This study provides valuable information on the potential effectiveness of appropriate workplace health promotion campaigns for SMEs and public health practices.