What's worked better for me is the "startup scholarship" that a lot of companies are doing now. A year is far enough away that we'll either be out of business or have the cash to pay, and I don't need to worry that I'm getting my money's worth by the time the 60-day trial ends.
I'm a big fan of Posthog right now because they have both a generous free tier & a generous startup scholarship. I've moved a ton of stuff to their platform.
A lot of it probably depends on your product though. If you're solving a very targeted problem then you might not be able to create a reasonable free tier. But a lot of B2B tech stuff is like... sure you can charge a bunch of users $5 apiece, but you risk missing the signup of the one user that was going to pay you $10k. Anything with usage-based pricing is going to have Pareto distributed revenue and you need to do everything you can to make sure you're capturing those customers on the tail.