It reminds me of https://startplaying.games/ which matches DMs/GMs with people that want to play dungeons and dragons and other TTRPG games online. Pricing is per person per session. Some of the DMs might be able to hit that $350 price point but it'd be for a 3+ hour session and their value add is very very obvious with number of games/hours they've DMd and reviews from players at their tables.
There's also a bar trivia company in Denver that's been hosting bar trivia over zoom - I think pricing is per team with some fun prizes. They support many more people than what you are offering too though. I have participated in a bar pre-covid and on Zoom and both experiences were fun.