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Women’s labor force participation has increased steadily in Germany over the last decades. Nowadays, half of all employees are women making them a central part of the German labor force and an indispensable group for German firms. Nevertheless, women are still primarily responsible for household and family work—especially after a child is born, and therefore increasingly face the challenge of reconciling career and family. This leads to a growing need for firms to offer family-friendly working conditions that relieve their (female) employees, which is observable at last in rise of organizational family-friendly arrangements. Yet, the effect of these arrangements has hardly been studied. We address this research gap and analyze how specific organizational family-friendly measures affect a sticking point in women’s career: the employment interruption after childbirth. Using linked employer-employee data, we investigate whether the observed arrangements can support a faster re-entry after childbirth. Based on time-specific piecewise constant models, our results reveal that organizational family-friendly measures have a positive effect on the reconciliation of family and working life leading to faster re-entries of women after childbirth and hence pay off for both, the firm, and the employees. However, the effects of the measures are determined by the structural context and vary according to the phase after childbirth.