At this level, I wouldn't call anyone. In my experience, the best publicity is news stories written by other people. Many years ago, when I was the best ram per dollar deal around, a blogger's benchmark that made the reddit and hn front pages took my business from almost nothing to "I can quit my dayjob" money in a very short period of time. I bet if the OpenSSL folks announced this soonish, the sales work would be done by the media. In fact, I think this is the big advantage of the low-dollar small-business accounts. You can say "here is the deal, take it or leave it" and wait for people to take it. For the big corporate deals, you have to meet and call and actually sell.
And for invoicing at this scale, use cashflow accounting. The sale closes when you receive payment. There will be some work matching up checks to logos, but at $1000 a pop, the 5% of customers who don't write the account identifier on the check are worth tracking down.
You do need to do accounting, but you need to do accounting at the current $2000/year level, too. I don't think they are committing themselves to all that much extra work if they only get a few buyers.
I have... intimate experience with the "I got too many customers before I had sufficient automation" problem... and yeah, it is a problem when you have $50/yr customers. It is not a problem, I think, when your smallest customers are $1000/yr.
And for invoicing at this scale, use cashflow accounting. The sale closes when you receive payment. There will be some work matching up checks to logos, but at $1000 a pop, the 5% of customers who don't write the account identifier on the check are worth tracking down.
You do need to do accounting, but you need to do accounting at the current $2000/year level, too. I don't think they are committing themselves to all that much extra work if they only get a few buyers.
I have... intimate experience with the "I got too many customers before I had sufficient automation" problem... and yeah, it is a problem when you have $50/yr customers. It is not a problem, I think, when your smallest customers are $1000/yr.