How do you approach enterprise demand gen differently at an organization that historically relied more on free trials and word of mouth?

This will require a mindset shift across the organization, so you'll want to be mindful of how it is communicated. Here is a high-level approach to the steps I would recommend:

1. Document your target audience: What is the ideal customer profile (ICP)? What has worked and what hasn't worked well from the perspective of reaching this audience?
2. Craft a demand generation strategy: Develop a target account list in partnership with the sales team. Think through the digital layers of outreach and the complementary touchpoints.
3. Develop sales enablement materials: It's critical to develop a relationship with the sales team. Agree on the assets that the sales team needs to set them up for success (e.g., battle cards).

This is largely dependent on stakeholder management and getting alignment across the team. Speak to the benefits of scaling past free trials and word of mouth and further filling the pipeline. This will enable you to capture a larger yet still targeted audience.