Mike, Lane is right on. If you don't have someone who knows what they are doing in Sales then hiring a sales rep is a waste of capital. Salespeople sell. They don't create strategy, develop lead programs Train themselves, or hold their own feet to the fire. That's what sales managers do. If you did find a salesperson who does all those things chances are you couldn't afford him or know one when you see one. And he would probably insist on straight commission because nobody can pay him what he is worth.
The average startup (and most sales depts. in mature companies) do the same thing you did because they can't evaluate salespeople on an interview either. One of the things we do here at JPM Partners is to recruit salespeople using a proprietary software to separate the performers from the talkers, and then we go one step further and tell our clients where the salesperson is strong and needs more training in the sales process. Guess who 95% of our customers are? Sitting down? Other recruiting firms who specialize in tech, education, healthcare, etc. Because sales in so specialized that they know what they don't know! Also because they've already made enough mistakes hiring the wrong peopleand spent enough money on the costly trial and error process.
After 25 years of running sales organization for corporate turnarounds and startups I can talk about this all day. Make that all week! LOL There are other options open to you and if you contact me offline I will share with you what they are - some of which are risk free and perfect for a budding startup like yours. Email me at email@example.com
All the Best,
What Rob said.
Mike you haven't talked about how you have structured your compensation schemes and what winning a typical deal will get a sales person. I've only had a peripheral involvement in technology sales to Schools and SDs but what I remember from that is that the sales cycles are simultaneously long and compressed -
ie you often have a long cycle engagement with multiple clients and then suddenly in the space of a few months, 75% of the good prospects want to close. This has to do with how the budget cycles work in SDs. So you may have unrealistic expectations of the sales reps and similarly your sales reps may have unrealistic expectations of the process.
Frankly though, if you are not willing to get involved in a weekly engagement with your sales teams, and to use your passion to close the "borderline deals" - then I'm not sure you have what it takes to be an entrepreneur. Either you are "all in" or you are not.
Think of it this way - lets say you DO become "that guy".
Frankly at the stage you seem to be at, I would expect your sales folks to be 100% commission based, no salary with a solid quota set on a monthly or quarterly basis with an expectation of hitting the quota 3 out of 4 quarters or 10 out of 12 months.
And if after a year (assuming a sales cycle under a year long) they haven't met that- then you find a replacement. You are not in the position of having the cashflow to spend on sales evaluation or training programs.
What you do need is at least a monthly meeting with your Sales Reps to discuss what is working, what isn't, and what their sales pipeline looks like (that's another thing that its hard to help you with. You are simply saying you don't think you are selling enough. But you haven't told us where in the sales pipeline things are falling down - I wonder if you even know)
Tradeshows can be a good source of sales - but more ideally they are a source of qualified leads for your sales team to go after. And you should be following up with every customer to gauge their level of satisfaction.
Then with the satisified ones you need to either ask for references or ask for case studies to take into future sales engagements