I think you go freemium if the market is large enough to support the idea that if you just convert a small percentage of customers, you'll still be a successful

I think you go freemium if the market is large enough to support the idea that if you just convert a small percentage of customers, you'll still be a successful company. If the answer is yes it's large enough, then whatever strategy gets your software in the hands of the most number of users should be the path you follow. Now, as a startup, I wouldn't start by competing head to head with OpenTable's salesforce going after their customers. That sounds expensive. Also, getting people to switch providers is always way more difficult. Plus, I think people value OT not because of their features but because of the network effect they bring. Don't get me wrong, you'll definitely still be going one-by-one and converting users, but I don't think you should start with those using your competition. Instead start with new restaurants or those not using anything. To them, you'll feel like a miracle. The reason you want to maximize distribution of software and engagement (having something that even the free plan is worth talking to people about) is because going freemium is not unlike investing in startups or building up a portfolio. You invest in your customers in mass (with free features not money) and you hope a small grouping of them will make back that investment many fold. Like investing, freemium works best as a long term strategy. So when you look at your upgrade triggers, be sure not to cripple that free plan so much that you're optimizing for conversion rate for users as SOON as possible. Convert them when they've grown to be successful. So they can say you were a key part of their success. I think MailChimp thinks about this really well if you haven't read their ideas already: http://blog.mailchimp.com/going-freemium-one-year-later/ http://blog.mailchimp.com/going-freemium-one-year-later/ Good luck!