Moving from a traditional one-time software license & maintenance price model to a subscription fee model

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.

Are you the manufacturer or reseller? If you are the reseller, typically about 40-50% above cost. Use the MSRP as an indicator.

I started a large SaaS Company for B2B where perfection in code is as importante as it gets. So here is my advice, DON'T CODE until you know what the Saas Really is. First start understanding what the problem REALLY is. Interview people and actually spend 100% of your time doing Customer Discovery. (This sounds easy but it is a skill you'll have to develop far more important than coding). Once you understand what the problem is, come up with a value proposition. Still no code. Then make a sell. If you can actually find things already existing that you can Hack and put it together then use that. Then make another sell. If you can sell it to at least 50 people if you are B2C, or if you are B2B you should have at least 1 customer. Once you do that then start automating some parts of the solution that you have hacked and so on. But THE most important thing is to be in constant conversations with your customers and hot leads. Remember you are a customer making machine not a coding machine, the first one is where the money is. Hope this helped you, if you want to talk more about customer discovery and customer development, just give me a call.

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.

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.