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America's Cup skippers like Russell Coutts get paid in the millions of dollars per year. This is the pinnacle of the sport and the most highly paid are the 'afterguard' (i.e the skipper, tactician, navigator etc). It depends on how well you do and also who you are sailing for. On the professional circuit, a pro sailor with an excellent CV (and say America's Cup experience or Volvo) gets paid in the order of 100k to 200k per year (in USD). Jobs are usually found via word of mouth and it's all about 'how you know' as well as how good you are.
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