Approaches presented herein enable tailoring messages to enhance sharing and resonance based on a community fingerprint and a key influencer. More specifically, a message to be directed to members of an online social community is received. Members of the social community who influence the social community and their likelihood to re-share messages are identified. A re-share fingerprint for the identified influencer is generated that maps the influencer's likelihood to re-share content. A communications fingerprint of the community is also created using an amalgamation of the communication patterns and styles of individual members of the community. The received message is optimized to most effectively target the message to the online social community and to solicit a desired response from the community based on the community communication fingerprint and the re-share fingerprint of the influencer. The optimized message can then be forwarded to the online social community.
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