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If you have an enforceable contract, the client is obligated to pay for the services received. As a business owner, I would be very concerned if a SAAS was demanding upfront payment for 2 years.

I hate to be the bearer of bad news, but generally, these are not the types of businesses that venture capital pursues. Due to the risk they are taking, VCs generally want to see a large market (meaning $1B potential) and a significant return on their money (10 times return). However, you can look for an Angel investor. These are generally individuals who are not looking for as large market or a return.Here are some places to start. Best of success to you! http://www.forbes.com/sites/tanyaprive/2013/12/16/20-most-active-angel-investors/ http://www.cbinsights.com/blog/top-angel-investors/

Source: I founded www.buyads.com and www.isocket.com, which powers the direct ad sales for the web's best sites (like TechCrunch, AOL, Microsoft, etc) We hand invited the publishers that join our market because, as your question suggests, there is some threshold between who should and should not try direct sales. There are no hard rules, just guidelines. The superseding one is this: Do you have inventory (audience) an advertiser would take the time to specifically work with you for? If you open a "store" and starting selling this stuff, do people want to buy it? One measure is traffic, but that's not enough. In general we like to look for sites with 100,000 page views a month or more. But it can depend on the content and vertical. For example, we power a website that gets 25k hits a month but is the only site covering the voice over talent industry in Hollywood - so its super nichey and there is a market for those advertisers. Other examples of small but successful premium properties include some hyperlocal ones (www.queensmamas.com, www.brooklynheightsblog.com, www.brokelyn.com, etc), the largest blog for truckers, largest blog for prison wardens, etc. The conflicting examples are sites with large traffic but bad audiences/verticals. We reject a lot of "tech blog" also-rans that just copy and paste content from TechCrunch but get a lot of SEO traffic from it. Or even if it's a legit site, it can be in a bad brand-advertiser vertical like home finance / mortgages (which is mostly lead gen advertisers)

You would want to hinge the purchase on a key feature that gives you a competitive advantage - and that is not fully incorporated in the trial version. I have advised SAAS Product Managers and your dilemma is certainly a shared one - getting customers to pick a) paid over free/basic/trial and b) getting them to pick the most lucrative package of the paid ones. If as you say, the software is complex, then we need some interface-based simplicity: try explainer videos for starters. http://www.powtoon.com/ So in sum - a friendly interface, and feature-based price marketing are two good places to start. Happy to have a conversation with you for further details.

You need leverage. The objection "you might not be around in awhile" is semi-valid but not a deal-killer. Something else was missed. "So are you saying you would NEVER, under any circumstances, work with a company less than a year old?" I'd go back to prospects who have turned you down and ask for open, honest feedback. Tell them it doesn't matter now, since they said no anyway, meaning it's not going to hurt your ego and you really want to know the real reason. In future presentations, don't bring up the age of your firm. Have a proven industry spokesperson endorse you. Develop a ton of content that shows you are in the field, are known by other people in it, and are at the forefront of whatever it is you do. And make sure your SaaS really does solve a HUGE problem for your market. Why does your marketplace--not YOU--say they need it? Remember that your customers survived to this point without it. Why should they change? There are many other sales process factors that we cannot see from the outside here.