How do you make sure you're listening to your customers?

Be your customer as much as you can. Try everything you make multiple times in different scenarios. There's a reason companies like Starbucks and DoorDash have programs in place that put their corp staff on the ground - it opens your eyes to things that you might not have otherwise spotted.

I'm also a huge fan having a regular forum for your teams to interact with your customers. In the enterprise setting these can be Early Access Programs that have select customers try out new products ahead of time for unfiltered, early feedback. In a more consumer world you can build the scaffolding for communities of users to come together. For example, when I was working on Google Maps, we had a high touch relationship with some of the top Local Guides that contributed to our map through UGC. Hearing their pain points and wishes helped shape our roadmap.