In this paper, we examine the visual variability of objects across different ad categories, i.e. what causes an advertisement to be visually persuasive. We focus on modeling and generating faces which appear to come from different types of ads. For example, if faces in beauty ads tend to be women wearing lipstick, a generative model should portray this distinct visual appearance. Training generative models which capture such category-specific differences is challenging because of the highly diverse appearance of faces in ads and the relatively limited amount of available training data. To address these problems, we propose a conditional variational autoencoder which makes use of predicted semantic attributes and facial expressions as a supervisory signal when training. We show how our model can be used to produce visually distinct faces which appear to be from a fixed ad topic category. Our human studies and quantitative and qualitative experiments confirm that our method greatly outperforms a variety of baselines, including two variations of a state-of-the-art generative adversarial network, for transforming faces to be more ad-category appropriate. Finally, we show preliminary generation results for other types of objects, conditioned on an ad topic.