What are you marketing ? To who (be specific) ? What is your vision for your product/company? Budget constraints ( there always are.) How is your competition marketing ? Local ? National ? Global ? There is never one simple answer to such a question. Give it some thought, hopefully you have already. Then lets talk about how I may be able to help.

I would go with promoting the matchups for two reasons, 1) People identify with causes not formats. 2) If the matchups are well paired the natural competition should drive contributions Personally I am intrigued by your concept and will be following how you develop.

Start with where you hope this expert's advice will get you. Be as specific as possible about as many details as possible. Then walk backward during your conversation to where you are now. I'm sure the expert knows a lot of things, about a lot of things. Your challenge in structuring the conversation is to laser focus on those things that will have a practical impact on your organization.

Bear in mind that you can delegate tasks, but not responsibility. As CEO your time is best spent making sure that all these different projects are all heading toward the common mission. Keep the information flowing to from and between the people you have delegated to. All of which is "important" just not the day to day "nuts and bolts" that you may be used to. You also need to remember you are the face of your company. What are you doing to make sure your community, industry etc. know about these exciting new things coming down the pipeline ? Your role as CEO is just as important as that of those you trust to implement your vision, just different.

the other issue with bringing in a tech co-founder is can you find one you can work with at that level and get along with personally. You don't want to solve your technical problem only to generate difference of vision issues down the road. A software development company also brings with it at least two major advantages. !) In many cases they can bring an entire team to build and test your app giving you a range of technical ability which would tend to improve the quality to the end user. 2) They may have existing contacts you can leverage from on the deployment and marketing side that would give you aa leg up there.

It helps to have a good support network. Including people who have started businesses would be great to have, if you have access to any. Friends, Your Spouse, your clergy member are also good candidates. In some ways it can be even better if they are not directly involved in your business that way they can provide some distance. The key things are first of all they need to be people you can trust, and confide in. Second they must be willing and have time to provide a Limited amount of ongoing support. If your business has or can assemble an advisory board, they can also be helpful here. The difference is an advisory board can have a bit of a conflict of interest of sorts advising you on the business, and the emotional ups and downs you are experiencing at the same time. They also cannot provide the prospective of distance as the other people I mentioned above.

Practice your "elevator pitch." for each segment you want to go after. By that I mean creating short, specific descriptions for what your product can do for each audience. Concentrate on BENEFITS to the prospective end user, not FEATURES. Hammer home how your product makes every hour of their day easier and more profitable. After you have done that get your message in front of your targeted professionals anywhere and everywhere you can. Go where THEY are ! This could include online webinars, trade shows chamber of commerce meetings etc.

This question is too vague to answer in any but the most general way. In general the first step is to identify what is the basic unit of business in your company. Is it a dollar of sales ? One Phone call taken ? One unit of your product produced etc. Then you have to decide what about that basic unit you want to measure. sales per day, units produced per hour, hours committed etc. Once these two factors have been determined in detail you can begin to look at what kind of system you need to measure them.

Before you can step away you need to make sure you have a proven system in place for delivering your product at the quality and service level that you expect. Then you have to recruit a sufficient number of key people who both share your passion for the product and where you want the company to go. Last you have to train those key people not only in the steps of your proven plan, but the reasons behind each step. Make sure this training includes how to react when the plan doesn't work as it usually does. You always have to be alert to the unexpected, and your team needs to know how to react when it pounces !