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Escaping the Wilderness Period and finally crossing the Penny Gap, requires clearly reverse-engineering your buyer and concisely answering the following questions about your product:

- Who exactly is the buyer?

- What immediate pain do you solve?

Find the lowest person on the org chart who might have all four attributes of the end user, business owner, technology owner, and budget owner. Sacks describes this as the “lowest atomic unit in the enterprise”. Then, sell to that person.

- Generating repeatable and non-associated revenue (e.g. “crossing the penny gap”)

- How does the team and its belief system need to evolve?

- Taking a consumer approach to enterprise

- Product positioning through category-creation

“A decade ago there was a really sharp divide between consumer and enterprise, these spaces were highly compartmentalized. We brought a lot of consumer thinking and consumer tactics to enterprise...Gradually over the last decade or so, the barriers have really come down, to the point where I think most founders see this consumerized approach as pro... See more