My main problem is that I didn't know how to find the exact type of person I'm looking for, so I cast a much wider net than I should have. I was told by an experienced salesperson that I should aim for ~100 emails per week, and then send followup emails to those same email addresses a couple days later, even if they don't respond to the first one, meaning I contacted ~400 people over the course of June. Part of the advice I received was that contacting the wrong person is okay, as they might forward me to the right person.

By the way, Apollo.io is a YC backed company, which was a huge part of my thought process. "YC? Based out of SF? Okay this must be how people do things these days." So against my better judgment, I gave it a shot.

It was definitely the wrong approach, but as someone with zero experience or knowledge of sales and cold outreach, there's no way I could have known that without trying first, especially with experienced salespeople telling me it's just what people do.