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 are borne from the belief (hope?) that there is some consistent, linear set of steps that can be designed and followed to ensure success for every one your accounts.

I know this dream. I’ve held it. I’ve designed plenty of playbooks (on both the Sales and CS side) — all of them some flavor of this:

sample visual of a customer success playbook

I’ve used this type of playbook with the stated goals of:

  • Ensuring success for our customers (follow these steps and success is yours! follow them not and…well); and
  • Making things easier for our reps (just follow the playbook for each account and you’ll never have to think about anything!).

But let’s be honest — these playbooks are really just management hacks. We mostly use them to hold our reps…



Derek Skaletsky

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