> 5. Reach out to the most senior person with a relevant role at each company with a personalized 1-on-1 email.
So, spam them, basically?
I'm not even "the most senior person" and I get tons of e-mails along these lines all the time. I am the asshole mail server admin who blacklists each one of them and submits their spam messages, though. At the least, I can prevent their messages from making it through to other people.
If you work for a SaaS company your CEO, your Head of Sales, your VP of Business Development are "spamming" other companies too in order to put food on your table. Read the history of famous startups and what tactics they used to get their first customers. "Naaaah they are just selling services and we're making the world a better place", right?
And my advice to other freelancers: This is why you never ever ever ever ever ever ever ever contact a tech person first if you want to offer your services to a company. Go to business people and decision makers. Avoid gatekeepers.
I completely agree, but often, the gatekeepers and decision makers end up being the same person. For example, it looks like if I were selling managed-email-servers-as-a-service, jlgaddis would be the person I want to talk to.
So, spam them, basically?
I'm not even "the most senior person" and I get tons of e-mails along these lines all the time. I am the asshole mail server admin who blacklists each one of them and submits their spam messages, though. At the least, I can prevent their messages from making it through to other people.