My VP Sales Playbook

aiming to lay down the foundations of my VP Sales playbook

Relevant note to check: !b2b-sales/setting-up-sales

👷🏼‍♂️ WORK IN PROGRESS 👷🏼‍♂️

04 Nov 2022


When starting in a (Sale) leadership position and to maximise success, I think DYR & DIY are critical.

DYR - Do Your Research

Always DYR (Do Your Research) when starting in a new VP Sales role.

No matter past experience, each company, product & context (eg target audience) is different, even within the same industry.

Research as much as you can before, at start and still intensively for months into your new role.


DIY - Do It Yourself

Do It Yourself.

Nothing beats learning by doing.

Hearsay, second-hand knowledge & data in spreadsheets or fancy dashboards are not enough.

Do the tasks yourself, and learn from your own experience.

You are in a unique position, with your past experience & different skillset you bring to the table, to identify:

  • what could be done better
  • what could be done differently
  • what doesn't need to be done
  • what can be automated
  • what kind of profile you need to hire for that role (a set of tasks)

Target audience & how to sell to it


VP Sales has 2 levers:

  • quota-carrying reps
  • productivity per rep



Define ideal rep profile - for assessment & hiring.

Hire for:

  • people with something to prove (to others, or themselves)
  • growth mindset (eg open to feedback, willing to change, etc..)


  • do the right thing for the business even if not in the person’s benefit (selfless vs selfish) / leadership trait. Hard to gauge pre-hiring though.

Past success does not guarantee future success.
Hiring from BigCo. in a Startup rarely works.

Build a repeateable hiring process.

Keep the bar high. A C-Player hire will be like cancer in the team.


Don't be a glorified scorekeeper.

Be in the moment with your reps.

Understand strengths and weaknesses of each rep.
Make alignments accordingly (territory, role scope, training, coaching, etc..).


Have a 1:1 with each new hire every week for the first 3 months at least.


  • formal training outsourced
  • in-house
  • self-training
  • peer training from best colleagues



Get a v1 playbook in place before scaling your hiring efforts.

Assign an experienced rep to each new hire.

Get new reps to listen to call recordings - better than shadowing calls (can be weird for all involved).
And provide notes on what they took away from each, and what they would have done differently.

Sales playbook

Gather the team and list all discovery questions that work best.
Incentivise for contributions to the playbook - leverage effect.

Bonus for providing outstanding documentation before leaving when letting go of a rep.

Define ICP as clearly as possible - laser focus on the #1 tiers.

Sales process

Define common vocabulary.

Build a repeatable Sales process. !b2b-sales/process


3:1 pipeline coverage ratio.


80% of reps hit at least 80% of quota.

Misc / CRO playbook

CAC < 12 months.