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

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.

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

Here is a link to a basic model - http://monetizepros.com/tools/template-library/subscription-revenue-model-spreadsheet/ Depending on the purpose of the model you could get much much more elaborate or simpler. This base model will help you to understand size of the prize. But if you want to develop an end to end profitability model (Revenue, Gross Margin, Selling & General Administrative Costs, Taxes) I would suggest working with financial analyst. You biggest drivers (inputs) on a SaaS model will be CAC (Customer Acquisition Cost, Average Selling Price / Monthly Plan Cost, Customer Churn(How many people cancel their plans month to month), & Cost to serve If you can nail down them with solid backup data on your assumption that will make thing a lot simpler. Let me know if you need any help. I spent 7 years at a Fortune 100 company as a Sr. Financial Analyst.

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.

Whenever you assign them a task, break down the task into small chunks. Make the chunks as small as you can (within reason, and to the extent that your knowledge allows), and tell your devs that if any chunks seem large, that they should further break those chunks down into bite size pieces. For instance, for the overall task of making a new webpage, _you_ might break it down as follows: 1) Set up a database 2) Make a form that takes user email, name, and phone number and adds them to database 3) Have our site send an email to everyone above the age of 50 each week When your devs take a look at it, _they_ might further break down the third step into: A) Set up an email service B) Connect it to the client database C) Figure out how to query the database for certain users D) Have it send emails to users over 50 You can keep using Asana, or you could use something like Trello which might make more sense for a small company, and might be easier to understand and track by yourself. In Trello you'd set up 4 columns titled, "To Do", "Doing", "Ready for Review", "Approved" (or combine the last two into "Done") You might want to tell them to only have tasks in the "Doing" column if they/re actually sitting at their desk working on it. For instance: not to leave a task in "Doing" overnight after work. That way you can actually see what they're working on and how long it takes, but that might be overly micro-manager-y At the end of each day / week when you review the tasks completed, look for ones that took a longer time than average (since, on average, all the tasks should be broken down into sub-tasks of approximately the same difficulty). Ask them about those tasks and why they took longer to do. It may be because they neglected to further break it down into chunks as you had asked (in which case you ask them to do that next time), or it may be that some unexpected snag came up, or it may be a hard task that can't be further broken down. In any case, listen to their explanation and you should be able to tell if it sounds reasonable, and if it sounds fishy, google the problem they say they encountered. You'll be able to get a better feel of their work ethic and honesty by how they answer the question, without worrying as much about what their actual words are. Make sure that when you ask for more details about why a task took longer, you don't do it in a probing way. Make sure they understand that you're doing it for your own learning and to help predict and properly plan future timelines.