I don’t think this is a “web and email” problem. It’s a “we can cut costs by leaning on cloudflare/AWS’s competence so we don’t need any competence in house” problem. If you have 100+ employees, you should be self-hosting much of your infra (or multi-cloud’ing it if you really don’t care about data security) and have redundant CDNs you can switch between if cloudflare is down.