Solid post. Any advice for a founder on how to start engaging with users after a few years of _not_ doing that? Luckily we've had success despite our inability to get user feedback, but obviously we need to do better.
We did concierge onboarding and set up shared slack channels with many of our early teams. This made it really easy and expected to ask for more feedback and to have users give it proactively.
Community channels are key as you grow. Frankly this is an area where we've underinvested as we've been heads down building/shipping product and is going to be a huge area of focus for us in 2021. The job of the founder is to really to give people who love your product a venue to share their ideas, questions with other users. Customer advisory boards work well too.
If you're SaaS I'd start with sending automated emails to ask for feedback at key points in your customer journey. You might find this article I wrote to be helpful[1]. It covers those key points and also includes examples to make it easy!