In recent decades, several countries have implemented paid parental leave for parents. This paper discusses the correlation between paid parental leave—which in Austria corresponds with receiving childcare benefits—and changing gender role attitudes in different-gender parent couples. It draws on evidence from 42 semi-structured couple interviews (n = 42, 2021–2022) in which couples were asked how they arranged childcare, employment, and household chores and how they reached agreements with employers. The empirical data were first analyzed based on content and then by applying constructivist-informed grounded theory to investigate whether and how gender affected couples’ efforts to reconcile childcare, employment, and household chores and how employers responded to parental arrangements that challenged traditional gender role attitudes. Compared to other countries, Austria offers rather generous childcare benefits, including long leave periods. In addition, Austria has introduced a partnership bonus for parents who share childcare benefits 50:50 or 60:40. However, the number of couples who take advantage of these benefits is still low. In the presented research, parents who succeeded in sharing these childcare benefits were interviewed. All interviewees had taken at least five months of paid parental leave. The data were analyzed using a content-oriented approach and by applying informed grounded theory. The results show that a substantial number of fathers continued working in minor employment while receiving childcare benefits, in line with the prevailing assumption among employers that the man is the main family breadwinner. By contrast, mothers had to strongly insist that they could continue working during the early transition to parenthood. However, on an individual level and in specific domains, Austrian parents were able to successfully overcome traditional gender inequalities in reconciling work and family with the support of the newly implemented childcare benefits. The observation that in Austria, the share of fathers who take the income-related form of parental leave is higher than that of fathers who claim other forms of childcare benefits points to the importance of all parents having access to well-compensated parental leave, regardless of their income level before the birth of a child.