My assumption from your question is that a company would buy this for their managers to use. If that is the case, building a freemium version would not guarantee that the company would actually turn around and purchase the product (or premium version) in the future. If you have pilots with companies that are well established names, that should be enough to start trying to get new customers and generate revenue. The surest way to know if your product is good enough is to ask people to pay for it. The fact that you could use some money at this point, only reinforces the decision.