Has anyone increased SaaS subscription pricing by 100% and lived to tell the tale?

Most Software as a service vendors generally don't book annual deals except in highly specialized cases. Most customers prefer to be able to cancel/change anytime they choose. Also, deals done "offline" end up actually often being more trouble than they are worth to administrate especially for a $2988 ticket. Generally, companies don't view prepaying for SaaS products a year in advance as a "convenience" (to them) so if the debate is internal (not customer driven), I'd set this debate aside until it's requested by the customer. Most customers will request a discount to pre-pay annual service. Happy to talk this through with you in a call, to work through the specifics of your situation in more detail.

there is Balanced, Dwolla, Braintree but none of them seem to work in India yet.

It depends on a number of factors but I'd boil it down to two key things to start: 1) What is your real cost to provide a free plan or trial? 2) Who exactly is your customer and what are they used to paying and who and how do they pay today? When you say "online workforce marketplace" it sounds as though you're placing virtual workers. If that's the case, or if you're paying for the supply side of the marketplace, the question is how much can you subsidize demand? Depending on where you're at in the process, I'd also question how much you can learn about the viability of your marketplace by offering a free version, assuming again, that free is actually a real cost to you. I was part of a SaaS project that started charging people for early access based mostly on just a good landing page (we clearly stated they were pre-paying) and were amazed at the response. I've also run a SaaS product that offered free trials and realized that the support costs and hand-holding and selling required to convert from free trial to paid wasn't worth it, this despite the product's significant average ARR. You might be better off providing a "more information" sign-up form (to capture more leads) and let them ask for a free trial while only showing your paid options. I've been amazed at the lead capture potential from a simple "have questions? Click here and we'll contact you" This is all the generalized advice I can offer based on the limited information I have, but happy to dive-in further if you'd like on a call.

I'm a product developer, startup veteran, and advisor to SaaS companies. Hopefully you've been already developing this new product with input from your existing customers, letting them beta test it and give feedback. (If not, my advice is to STOP immediately and get enough pilot customers involved to be sure that you're delivering something really valuable to them, that works the way they expect it to work, is easy to understand and get started with, etc.. The last thing you want is to do a big splashy launch of a product that is D.O.A. because you built what you assumed the customers wanted instead of they actually demonstrated that they wanted.) OK, so let's assume that you've got customers in the loop. Interview the heck out of them. Really understand how they use the product, why they use the product, what makes it valuable to them, what they can do with it that they couldn't do before, etc. If the product's not done enough for them to be best testing it yet and getting results, at least get some insights into how they see themselves getting results from it. How does it/will it change their lives? As you do this, be on the lookout for things that really resonate. Emotional language, for example. "It's such a relief that I don't have to worry about sending invoices manually anymore." (or whatever pain it is that your software solves) Also look for (and try to elicit) specific result statements: "This new software saves me [or is going to save me] 15 hours a week. Now I can spend that time where I really want to, with my kids ( ... my cat ... my golf buddies ... )" You're doing this for three reasons: 1) This stuff makes for phenomenal testimonials; 2) it helps you come up with great ideas for pre-launch content; and 3) it generates *PURE SOLD GOLD* you'll use in writing the copy for your launch offer. OK, launch mechanics. There are people who teach huge long expensive courses on this stuff. I'll give you the Cliff's notes. While I haven't personally run a major product launch, I have been trained in the strategy and am very familiar with it. - Plan your launch period in advance. You might want to do a pre-launch sequence that lasts 1, 2, even 3 months depending on the magnitude of your product and how much effort you're willing to put into creating content for the launch. - Create some teaser content of interest to your customers who might want to buy this product. Offer to teach them something, or offer to give them a sneak-peak behind-the-scenes of your new product. - Send an enticing offer for this content out to your list. Get people who are interested in this content to sign up for it. This creates your launch email list. - Send your launch list weekly updates: development milestones, sneak-peak screenshots, videos, educational material, interviews with/testimonials from beta users, and so on. - You're not trying to sell here yet (not hard sell at least). Drop some hints that there is going to be a special offer when the product launches, just for special loyal customers like them. - Create at least three videos on topics that are really, really interesting to your prospective customers... not necessarily about your new product itself, but teach them about what they can achieve with it, or what others have achieved with it already. As you publish these videos, send the link out to your launch list. - Also send out an offer to see these videos to your main list, to entice more people to sign up for your launch list. - As you get closer to launch time, keep sending frequent updates to the pre-launch list, and send another email out to your main list to let them know that the product is launching soon, and that if they're interested in the special one-time-only launch pricing, they need to sign up for the "early bird list" (your launch list). - Send out a 24-hour notice that the launch is going to happen soon, and the launch pricing will only be available for a limited time (potentially, to a limited number of customers ... to increase scarcity and urgency). - I recommend that even if you plan to open the product up to all your customers that at launch time you limit it to a smaller number. This makes the inevitable post-launch gremlins less painful to deal with because you have fewer customers, and it motivates people to buy because they fear that they'll lose the opportunity to do so. You can open the product up to more people later... the delay will result in pent-up demand and easier sales. - Start the launch. Tell your early-bird launch list a few hours early, then tell your main list. Direct them to a web page with a video and long-form sales copy of your launch offer. - Send out 2-day, 1-day, 12-hour, etc. notices that the launch is ending soon and reminding people what they're missing out on if they don't act now. If you're offering a limited number of spots, tell people what percentage has already sold out. Remind people that if they're "on the fence" about this, that this is the time to make a decision. - Send out an email letting people know that the launch is over and thanking them for their support and their vote of confidence. Tell the people who didn't buy (or didn't get in) that you'll let them know that the product will be opening up for new registrations some time in the future. (You may get people sending you emails begging to be let in at this point, if your product is desirable and your marketing was executed well.) And, of course, you don't just have to promote your launch content to your existing customer list ... you can post it to social media (and encourage your customers to do so) to attract brand new customers into your world. If you'd like to go into more detail about launch planning for your specific product and market, I'd be happy to jump on a call and talk about ways to make this work for you.

For me personally, no. However, what you really need is a larger data set. Gumroad just did a post on prices ending in "9": http://blog.gumroad.com/post/64417917582/a-penny-saved-psychological-pricing 37signals started with prices that ended in 9: http://37signals.com/svn/posts/1287-ask-37signals-how-did-you-come-up-with-pricing-for-your-products ... but they later did research and found it didn't matter (for them). The answer for YOU will likely be to test these things for yourself on your SaaS app.