The Portuguese and Dutch merchant empires had a similar geographic distribution with outposts all around the Indian Ocean, which they controlled and manned. Both empires faced the same problem of monitoring their agents in remote corners of the world. Each, however, arrived at a different solution to the monitoring problem. I use a principal-agent model to link different monitoring options to the different organizational structures of the two empires. I further investigate the implications of the model with archival data on labor compensation for Portuguese and Dutch workers overseas.