My thoughts on “Playbooks” (and why they suck for PLG companies)

Derek Skaletsky
7 min readMar 31, 2020

I recently had a conversation with a top CS leader who was struggling to build and get their “Playbooks” to work.

My suggestion was — forget it. Playbooks suck. She was surprised at my take on this as the idea of Playbooks has been a pretty standard part of the Customer Success function for a long time. And I understand why.

Playbooks — when used in the context of a Sales or CS team — represent lists of “plays” (or actions) that a rep is required to apply against any new lead or customer. They…

Derek Skaletsky

Tech founder (mostly SaaS). Latest — Sherlock (; Boston expat; Hollywood escapee; hack photographer; dad (x2)