We'll definitely give pricing some thought, you're right that it's probably time to revisit.
Re: the video, actually now that I look back we used a company called xp-studios.com - we just provided the script. I believe it was around $3k but this was back in 2013.
I came to suggest the same. The prices feel way too low. If you haven't experimented a lot with these, I'd recommend trying it. If you have paying customers now, I suspect you could increase new monthly revenue by several multiples.
You mentioned wanting to play with paid ads. I think you'll quickly find that your current LTV is way too low to justify any campaigns (unless your enterprise plan is converting like crazy?)
(Unpopular opinion) Also consider experimenting with killing your free plan if your goal is to increase revenue. I'm not saying you definitely should kill it long-term - just experiment with removing the option in an A/B test and see how it impacts conversions on paid plans. Freemium normally benefits products with network effects. It's not totally obvious to me how your product might benefit from that.
Re: the video, actually now that I look back we used a company called xp-studios.com - we just provided the script. I believe it was around $3k but this was back in 2013.