1) I agree with your assessment - responding to "blind" pricing requests over email are unproductive. Before I provide that information, I always ask for a 10 minute introductory call, determine real buying intent, establish an initial relationship and connecting on LinkedIn is a more productive step.
2) Correct, I think what you are trying to do is create some urgency for the buyer. That strategy can work if there is a compelling event on their side, otherwise it is arbitrary and diminishes your position.
3) Agree, I always develop my pricing proposal (with input from the client/prospect) and I present it - I never email it 1st. Other people may have different approaches but to me, if you've put time and effort into a pricing proposal it needs to be properly presented.
4) Buyers are more educated and risk averse. You certainly can incorporate a "proof step" into the licensing phase.
5) Marketing - I would need to understand more about the point your making. In my opinion Marketing drives you brand, Sales drives your pipeline.
Please reach out to me if I can help.
Your observations reflect a wealth of experience for someone who is not a salesperson. There are many salespeople out there who don't understand those symptoms, let alone know how to make the necessary adjustments. I see some good interpretations and advice in these responses too. To add to the conversation:
1. If someone is visiting your site and asking about your service (and price), they either have a problem they think you can solve or they are a potential competitor. Email is terrible for dialog so if someone randomly emails you, ask for a call. Someone who is truly interested will take that call. I am assuming your service is customizable? If so, you need to assess the project and then you can give them a quote. Before you go into selling your service ask, "What are you looking for in terms of text intelligence and tell me how you resolve that today?". As they answer, resist selling your solution, keep wearing your therapist hat and keep asking open-ended questions like why, how and who, etc. You should uncover what is important to them and then you can focus your sales pitch on how it benefits them. The benefits are always more compelling to the buyer than are your product features.
2. Qualify each prospect for time, need and money. If they don't have anyone of those 3, they won't buy, not even with a discount. If you do discount, it needs to have an equal benefit to you (longer contract, bigger purchase, etc.) and only at the end of the negotiation... this assumes your product is not a commodity. If your product or service has unique attributes and it is the best fit for their problem, they will buy it at a fair value. Good buyers negotiate on price. Good sellers negotiate on value. To get to value, this assumes you have that good therapy/discovery session upfront.
3. You have a few different paths you can take and this will set the foundation for your sales model. 1. A different price = a different solution. Are there levels to your solution that you can upgrade/downgrade based on the price? 2. Have your entry price and know your bottom line. When you've reached that bottom line, say, "that's my best offer, can you move forward at that price?". 3. Do not negotiate your price at all. It is what it is, you've taken all this into consideration when you came up with the price and if you believe you have good value for money, you can say, "Your success depends upon my success. I need customers who are vested in me, that can grow with me and I can grow with them. A cheaper price for all my customers will force me to cut corners. You nor I want to compromise on quality and this price helps me reinvest back into improving the service. Can you move forward at that price?" If the price remains an issue, then maybe you are too high.
4. I think there is more to this observation - like how do I get repeat business or how do I get them to commit after the trial period. People typically want to do a trial to a) share it with others (get other influencers or buyers involved), b) see if it really works or c) see all the different ways it will benefit them. It's one of the reasons you need to have that therapy/discovery session upfront. It gives you more feedback on how the service benefits different customer types. It also helps you prioritize future improvements to the service.
5. There are various marketing channels that help drive inbound interest and drum up sales leads. Blogging is one of them and Jessica makes a great point about Hubspot's model. Generating fresh and relevant content is challenging, let alone placing it in the right trade press, business press, and other digital outlets. Having someone manage content development and placement could benefit the business.
As for other sales pointers, it sounds like you may be at an early stage where you need to drive awareness of either the problem that no one realizes they have or that a solution exists to this chronic problem affecting all your potential customers. Depending on whether you have broad applications or niche ones, you may be looking for a marketing person to help drive education & demand and/or a salesperson to drive demand and convert it into signed contracts. That will free up your time to improve the product and get on important client calls.
Other advice... If you demo your product (instead of doing trials), keep it short and to the point. Don't overwhelm them with all the different features and benefits, hoping they will figure it out. Assess what you think are the three most relevant points to the buyer. Show it and then be quiet, ask for their feedback. Then ask for the next steps...
All the best,