Free trials are a PLG cornerstone that rarely survive contact with enterprise procurement. Security reviews, legal sign-off, and misaligned buyer-user relationships all get in the way. This panel features operators who have designed self-serve motions that actually work inside complex buying processes. Panelists share how they structured trials to clear compliance hurdles, managed tension with sales teams who see self-serve as competition, and identified which enterprise segments are simply not a fit for a self-serve entry point. Attendee takeaways - Trial structures that have cleared enterprise security review without killing the self-serve experience - How to design the handoff between self-serve and enterprise sales so neither undermines the other - Which enterprise segments are genuinely unsuitable for self-serve and how to route them without losing the deal