Planning as Practice: A Masterclass with Adam Gross (Former CEO of Heroku, Vimeo)
Enrich members and select guests gathered for an eye-opening conversation with Adam Gross, former CEO of Heroku and a luminary in the product-led growth (PLG) space. The session was moderated by James, partner at Bloomberg Beta (an investor in Enrich), who introduced Adam as someone who "sees the future more clearly than most" and has "deep conviction about it."
With leadership positions at companies like Heroku, Dropbox, and Vimeo during critical growth periods, Adam provided a masterclass on PLG and driving company alignment.
If you'd been there, here's what you'd still be thinking about:
PLG is hard because it requires a much higher level of cross organizational collaboration and alignment than previous models. Organizations struggle to have the right kind of structure and processes to facilitate alignment when iterating and releasing new features happens much more frequently. This is in contrast to the “software CD era,” when a software CD came out, got passed to sales, and salespeople sold it. Go-to-market approaches have undergone four major transformations: from the traditional "fancy dress people at golf courses" model of the 80s-90s, to the SaaS revolution pioneered by Salesforce, to the PLG era initiated by companies like Dropbox, and now to the emerging PLG+AI model exemplified by companies like OpenAI, Anthropic, and Cursor.
The way to drive alignment is through very thoughtful and intentional planning processes. "If you're viewing it as a tax or administrative, something's wrong." The goal of your intentional planning process is narrative clarity. It should be as satisfying as watching a great movie with three clear acts. The way to get alignment is to tell stories.
Think about organizational planning as a practice. It’s like yoga or exercise, just doing it on a regular cadence is the point.
We also took great notes on avoiding the "enterprise mirage" of early traction, why Adam avoids OKRs and pricing consultants, and how user experience is the differentiator in successful AI products. To get access to the complete notes and attend future Enrich events with incredible experts like Adam Gross...join Enrich!
