Here's the data on my paying vs non-paying customers based on team size. I'd love any thoughts on pricing.

Cool mate. So this project is different to the gramreports product listed on your profile?
Feel free to shoot through any messages to me, but not too sure if you can do PM here on IH.

1. Increase the price if you think its undervalued for bigger team, they'll use it anyway.
2. Most of the smaller team will probably not convert even if you lower the price, but one thing you can do is run discounted campaign, like 50%-80% of only for smaller teams (less than 99 people) for next 6 months or a year, that may convert some them and if they use it for at least 6 month or year, they'll continue to use it when the price go back to normal. Also don't fix a end date for campaign and don't mention when its gonna end to the user, that way you can run the campaign as long as you want and end it whenever you'll feel like it and don't have to extend the campaign again and again if it doesn't do well.