Direct outreach on
LinkedIn completely flopped. Part of the problem, I think, is that I was looking in the wrong place.
LinkedIn mostly seems to be a place where businesses that have already "made it" show off their success, and the founders on there are pretty set in the way that they do things and the tools they use. I also think that
LinkedIn users, especially business owners, are numb to being pitched ideas and products in their DMs, so it's easy for them to disregard your message if they even see it at all.
What has worked the best, by far, has been direct outreach and personal conversations through
Facebook. There are tons of groups where my exact type of customer meets and asks for help. One post in the group saying "I need help managing my invoices" is worth a hundred cold emails or DMs on
LinkedIn.
I've found that it's important to be genuine when interacting with group members, and recognize that not every comment or message needs to be a sales pitch. Sometimes providing genuine advice is worthwhile to make a connection that leads somewhere down the road.