Deal Playbook logo

Deal Playbook

CommunityPopular
jeremylongshore
deal-playbook

Write sales playbooks — outbound sequences, discovery call guides, objection handling scripts, and demo frameworks. Use when asked to "write a sales playbook", "build an outbound sequence", "help me handle objections", or "design a discovery call".

Overview

Publisherjeremylongshore
Repositorytons-of-skills-marketplace
Skill namedeal-playbook
Stars
2.8K
Forks
409
Bundled files
Instructions only
LicenseMIT
Links
  • Markdown instructions

    A SKILL.md file the model loads on demand, so it only costs tokens when a request actually matches.

  • Works with any LLM

    AI skills are plain Markdown, not provider-specific code, so this works with GPT, Claude, Gemini, Grok, or a local model.

  • Self-contained

    Everything the model needs lives in the instructions — no extra files to sync.

  • Open source

    Published by jeremylongshore on GitHub. Read the source before you install it.

Installation

Install the Deal Playbook AI skill in TypingMind to use it with any LLM, or drop it into another agent that reads SKILL.md.

1

Install in TypingMind

TypingMind installs a skill straight from its GitHub folder — it reads SKILL.md, bundles the resource files, and stores the result locally.

  1. Open the app and go to Plugins → Skills.
  2. Choose "Install from GitHub".
  3. Paste the skill folder URL below and confirm.
    https://github.com/jeremylongshore/tons-of-skills-marketplace/tree/main/plugins/ai-agency/tonone/skills/deal-playbook
  4. Enable the skill in any chat where you want it available.
Plugins → Skills → Add skill → From GitHub URL, then paste the folder URL and press Continue.
2

Install in another agent

Any agent that reads the Agent Skills format can use this skill — copy the folder into that agent's skills directory.

Claude Code — .claude/skills
git clone --depth 1 https://github.com/jeremylongshore/tons-of-skills-marketplace.git /tmp/tons-of-skills-marketplace
mkdir -p .claude/skills
cp -r /tmp/tons-of-skills-marketplace/plugins/ai-agency/tonone/skills/deal-playbook .claude/skills/deal-playbook
Restart Claude Code after copying so it picks up the new skill.

Use it in TypingMind

Enable Deal Playbook in any TypingMind chat and the model takes it from there. Its name and description sit in the system prompt, and the moment a request matches, the model loads the full instructions itself — you never invoke it by hand, and it costs no tokens until it is actually used.

The model loads Deal Playbook on its own as soon as a request matches it.

Works with any AI model

AI skills are plain Markdown instructions rather than provider-specific code, so Deal Playbook is not tied to the model it was written for. Install it once in TypingMind and use it with GPT-5, Claude, Gemini, Grok, DeepSeek, Mistral, Llama, or a local model you run yourself — all on your own API keys.

  • Loaded only when it is needed

    The system prompt carries just the name and description. The instructions are fetched on the first matching request, so an idle skill costs nothing.

  • Switch models mid-chat

    Because the skill is instructions rather than code, changing model does not break it — the next model reads the same SKILL.md.

Skill instructions

This is the SKILL.md content the model loads. Read it before installing — a skill is instructions your model will follow.

Sales Playbook

You are Deal — the revenue & sales engineer on the Product Team. Write the specific playbook artifact requested.

Follow the output format defined in docs/output-kit.md — 40-line CLI max, box-drawing skeleton, unified severity indicators, compressed prose.

Steps

Step 0: Identify Playbook Type

Determine which playbook artifact is needed:

  • A) Outbound sequence — Cold email or LinkedIn sequence to generate meetings
  • B) Discovery call guide — Questions and flow for first sales conversation
  • C) Demo framework — Structure for product demo that converts to next step
  • D) Objection handling — Responses to the 5-10 most common objections
  • E) Proposal template — Structure and content for written proposals

Ask if not clear from context.

Step 1: Gather ICP Context

Before writing any playbook, capture:

  • Target role/persona (e.g., "VP Engineering at 50-500 person SaaS company")
  • Trigger event or buying signal (e.g., "just raised Series A", "team grew past 20 engineers")
  • Primary pain (buyer-level, not user-level — what does THIS persona lose sleep over?)
  • What they currently do instead (the status quo alternative)
  • One concrete outcome customers have achieved (proof point)

Step 2: Produce the Playbook

A) Outbound sequence (5-touch, 2 weeks):

Touch 1 (Day 1) — Email: Specific trigger + one-line value + soft CTA
Subject: [specific to trigger event]
Body: [2-3 sentences max. Prove you did research. One clear ask.]

Touch 2 (Day 3) — Email: Different angle, same pain
Touch 3 (Day 5) — LinkedIn connection request + note
Touch 4 (Day 8) — Email: Proof point (customer outcome)
Touch 5 (Day 12) — Email: Breakup (explicit close)

Personalization variables to fill per prospect:

  • [TRIGGER_EVENT]: specific reason for reaching out
  • [SPECIFIC_PAIN]: their exact problem
  • [OUTCOME]: one concrete customer result

B) Discovery call guide:

Pre-call (2 min): Confirm agenda. "I have 30 minutes — is that still good?"

Opening (5 min):
- "Tell me what's going on with [problem area] right now"
- Let them talk. Don't pitch.

Discovery (15 min):
- "How long has this been an issue?"
- "What have you tried? Why didn't it work?"
- "What happens if you don't solve this in the next 6 months?"
- "Who else cares about this problem?"
- "What would solving it mean for you personally?"

Value hypothesis (5 min):
- "Based on what you've said, here's what I think we can do..."
- One specific outcome, not feature list

Next step (5 min):
- Never end without a committed next step. Date + time.
- "Who else needs to be in the next conversation?"

C) Demo framework (30-min demo):

Setup (5 min): "Before I show you anything, tell me your one biggest goal for [use case]"
Demo (15 min): Show only the 3 features that address stated goal. Nothing else.
Proof (5 min): One customer story in 60 seconds. Same role, same pain, measurable outcome.
Next step (5 min): "What would it take for you to move forward?" Then close on specific date.

D) Objection handling:

For each objection, produce:

Objection: [exact words prospect uses]
What they really mean: [underlying concern]
Response: [2-3 sentence response that validates + reframes]
Probe question: [question that moves conversation forward]

E) Proposal template:

markdown
# [Customer Name] — [Product] Proposal

## Your Situation

[2 sentences summarizing what they told you in discovery. Prove you listened.]

## What We're Solving

[Specific outcome, not features. Quantified if possible.]

## Our Recommendation

[1-2 recommended options, not 5]

## Investment

[Clear pricing. No surprises.]

## What Happens Next

[3 steps, each with owner and date]

## Why Now

[Stakes of not acting. Specific to their timeline.]

Step 3: Calibrate for Stage

  • Stage 1 (founder selling): playbook is informal guide. Focus on discovery quality.
  • Stage 2 (first reps): playbook is strict script. Rep deviation is the problem. Make it repeatable.
  • Stage 3 (sales org): playbook is enablement asset. Must survive onboarding of 20 reps.

Delivery

Produce the complete playbook artifact as a markdown document, ready to drop into Notion, Confluence, or a sales playbook system. Include a one-line "when to use this" header. If output exceeds 40 lines, delegate to /atlas-report.

Frequently asked questions

What does the Deal Playbook AI skill do?

Write sales playbooks — outbound sequences, discovery call guides, objection handling scripts, and demo frameworks. Use when asked to "write a sales playbook", "build an outbound sequence", "help me handle objections", or "design a discovery call".

Why use Deal Playbook on TypingMind?

Because you install it once and use it with any model. Deal Playbook is plain Markdown rather than provider-specific code, so the same skill runs on GPT-5, Claude, Gemini, Grok, or a local model — and you can switch model mid-chat without it breaking. TypingMind runs on your own API keys, so you pay providers directly instead of a per-seat subscription, and your skills and chats stay in your own storage.

How do I install Deal Playbook in TypingMind?

Open Plugins → Skills → Install from GitHub in TypingMind and paste https://github.com/jeremylongshore/tons-of-skills-marketplace/tree/main/plugins/ai-agency/tonone/skills/deal-playbook. TypingMind reads its SKILL.md and installs it as a skill you can enable per chat.

Which AI models can use Deal Playbook?

Any model you connect in TypingMind. AI skills are plain Markdown instructions rather than provider-specific code, so GPT, Claude, Gemini, Grok, and local models can all load this skill when a request matches it.

How many AI models can I use with Deal Playbook?

As many as you like. As long as a model supports skills, you can use Deal Playbook with it — GPT, Claude, Gemini, Grok, DeepSeek, Mistral, Llama and more — all on TypingMind with your own API keys.

Is the Deal Playbook AI skill free?

Yes. It is published on GitHub by jeremylongshore under the MIT license. You only pay your own AI provider for the tokens you use.

What are AI skills?

An AI skill is a reusable instruction bundle that teaches an AI model how to do one specific task. It follows the open Agent Skills format: a SKILL.md file with a name and description, plus any scripts, templates or reference files the model may need. The model reads the instructions only when your request matches the skill, so an installed skill costs nothing until it is used.

How are AI skills different from plugins or MCP servers?

A plugin or MCP server gives a model new tools to call — code that runs somewhere and returns a result. An AI skill gives the model knowledge and process instead: how to approach a task, which steps to follow, what good output looks like. Skills are plain Markdown, so they need no server, no API key and no runtime, and they work with any model.

View all

Set up your own AI workspace now

Get notified about new features and future giveaways by subscribing to our newsletter 👇