Oh, the classic demo sign-up leak - it's like watching water slip through your fingers. Most of the drop-off between signup and demo is just lazy scheduling. Send a damn calendar link the second they hit submit, not three hours later. And a reminder 24 hours out plus another one hour before? Slashes no-shows by about half. It's not rocket science, it's basic courtesy.
Post-demo vanish is nearly always a qualification fail. You're demoing to people who aren't ready to buy, so they ghost. A pre-demo qualification call fixes this, but it cuts demo volume, which scares the bejesus out of teams who'd rather just demo everyone and pray.
Trial-to-paid crashes when the "aha moment" doesn't happen in session one. Find the one action that correlates with paid conversion - the single thing that makes someone go "I need this" - and obsess over getting them there. Everything else is downstream of that.
Free trial to paid is just the final chapter of those three mess-ups. Fix the leaky pipeline, not the bottom of the funnel.