I need to know more about the type of software you are developing and how big the team will need to get in the long term. A few key rules: 1) Your first 10 people should be the best you can find - alter the organization to meet capabilities of the first 10 employees. 2) Don't hire anyone who is not exactly what you are looking for (Go without until you find the right person) 3) As CEO, stay hyper focused on product management - if you define the wrong product features, your organization no matter how it is structured, will waste its time. Frankly the CEO should probably do Sales/Marketing for a while. 4) For book keeping and such find a mother who's kids are in college. She is great at managing chaos and will compensate for your ADHD (all great entrepreneurs have ADHD). 5) No part time people on core jobs (i.e. development) 6) Don't outsource any part of the product that is close to the customer feedback loop. i.e. don't outsource the iPhone app if that is 90% of how you engage customers. You need a really tight lean update loop on product requirements/product evolution.