# Sales Enablement

> Use this skill when the user needs sales-facing materials, founder-led sales process design, or call-execution artifacts — pitch decks, one-pagers, demo scripts, sales FAQs, battlecards, objection handlers, discovery questions, proposal templates, or stage-by-stage sales process. Triggers include any mention of 'pitch deck', 'sales deck', 'one-pager', 'demo script', 'sales FAQ', 'battlecard', 'objection handling', 'sales call', 'discovery call', 'proposal', 'founder sales', 'sales process', 'pipeline stages', 'closing process', 'sales motion', or 'help me prep for a [sales/demo/discovery] call'. Reads `pmm-context.md` and (if available) positioning, persona, and outreach artifacts first. Outputs founder-grade materials — short, specific, defensible — not enterprise SaaS templates. Do NOT use for outbound prospecting messages (use `outreach`), for marketing/lifecycle content (different category), or for adapting messaging to competitive moves (use `adaptive-messaging`).

- Skill: `dirknicol/sales-enablement` (Agent Skill, multi-file: 2 files)
- Install (CLI): `npx skillmds@latest add dirknicol/sales-enablement`
- Raw SKILL.md: https://api.skillmd.com/api/skills/dirknicol/sales-enablement/raw
- Safety review: pending
- Works with: Claude Code, Claude.ai, OpenAI Codex
- Category: Product & Planning
- License: MIT
- Author: dirknicol (https://skillmd.com/u/dirknicol)
- Updated: 2026-09-17
- Page: https://skillmd.com/skills/dirknicol/sales-enablement

---


# Sales Enablement

## What this skill does

The materials and process you need once someone says yes to a call. Pitch decks (multiple lengths), one-pagers, demo scripts, sales FAQ, objection battlecards, discovery question sets, proposal templates, and the stage-by-stage sales process to thread them together.

Built specifically for **founder-led sales** — solo or small teams running their own deals. Not for SDR-driven enterprise sales motions where these materials get handed off through a long chain.

The implicit assumption: the founder is the salesperson, the demo-er, and the closer. Materials must be tight, defensible, and credible at every stage.

## When to invoke

- User just booked a discovery or demo call and needs to prep
- User is going into a sales sprint and needs the artifact set
- User is improvising sales materials each call and wants to standardize
- User got a specific objection and needs a structured response
- User needs a proposal template they can adapt to specific deals
- User is hiring their first salesperson and needs to document what they've been doing intuitively

## Prerequisites

1. **Read `pmm-context.md` first when available.** Pull voice, positioning, proof points, and claim boundaries. If it is missing, offer to run `pmm-context`. If unavailable or declined, collect a minimum brief covering offer, persona, sales stage, proof, pricing or commercial model, constraints, and voice. Mark assumptions and continue.
2. **Read positioning and persona artifacts if available.** Pitch and demo should be specific to the persona; battlecards depend on positioning.
3. Ask what the user actually needs:
   - Specific call to prep for? (Discovery vs. demo vs. closing — totally different prep)
   - Full artifact set, or one specific piece?
   - Which persona is this for? (Agency vs. RIA vs. enterprise — different decks)
   - What stage of sales motion are they in? (First demo, repeat motion, hiring their first AE)

## Core principles

These shape every output:

1. **Founder-grade, not enterprise-template.** A founder pitching their own product should never use a 60-slide McKinsey deck. 5-15 slides, specific claims, real customers, founder energy. The deck should feel like the founder talking, not a corporate brochure.

2. **Discovery > demo > pitch.** Spend most of the conversation understanding the buyer, then show only the capabilities relevant to what you learned. Keep the generic pitch brief.

3. **One proof point per claim.** Every claim in any sales material needs a specific proof point — customer name, metric, evidence tier, or credible source. Unbacked claims kill credibility.

4. **No language we don't use.** Sales materials must match the voice in `pmm-context.md`. If founder doesn't say "leverage cutting-edge AI," neither does the deck.

5. **Stage discipline.** A discovery call doesn't end in a quote. A demo doesn't end with a contract. Each stage has a clear exit criterion — what has to be true to move to the next stage.

6. **Objections are signals, not obstacles.** A real objection means the prospect is engaged. Handle them honestly and specifically. Generic objection scripts ("I hear that a lot, but...") destroy trust.

7. **The deal is in the follow-up.** Most deals close (or die) between meetings, not in meetings. Sales materials must include what to send when.

## Workflow

### Step 1 — Scope what the user needs

Don't generate everything. Ask: what's the specific artifact or moment they need help with?

If user says "help me with sales" — too vague. Push to specific:
- Prepping a call (which stage?)
- Building a deck
- Drafting a proposal
- Building a battlecard
- Designing the overall sales motion

### Step 2 — Pull the right context

Use `pmm-context.md` when available; otherwise use the task-specific brief gathered in Step 1.

Then conditionally:
- For pitch deck → positioning + personas
- For demo script → personas + the specific product capabilities
- For battlecard → positioning + competitive analysis (if it exists)
- For proposal → positioning + pricing decisions
- For discovery prep → personas + `customer-research` skill's interview guide patterns

### Step 3 — Generate the artifact(s)

Specific patterns by artifact in the sections below.

### Step 4 — Define the call flow (if relevant)

For prep on a specific call, include not just the materials but the call flow: minute-by-minute structure, what to ask, what to show, what to skip.

### Step 5 — Define the post-call follow-up

What gets sent within 24 hours of the call. This is where most deals progress or die.

## Artifact patterns

### A. Pitch deck (5 / 10 / 15-slide variants)

**5-slide version** (for warm conversations, founders, peer pitches):

| Slide | Content |
|---|---|
| 1. Hook | The problem stated in the buyer's language. One sentence. |
| 2. Why now | The market shift making this urgent now. One concrete data point. |
| 3. What we do | The category + the one-sentence value prop. |
| 4. Proof | One customer story or specific outcome. |
| 5. Ask | What you want from them, specifically. |

**10-slide version** (for prospects, agency principals, demo opens):

Adds: persona context, before/after, differentiator vs. alternatives, founder credibility, pricing or commercial model.

**15-slide version** (for warm prospects, late-stage demos):

Adds: 2-3 use cases, deeper differentiator content, customer-by-segment validation, roadmap teaser, FAQ.

Specific guidance:
- Every slide title should make a defensible claim, not describe a topic. ❌ "The Market" ✅ "Buyers are adding AI assistants to product discovery"
- Every claim slide should be backed by one specific source on the slide
- No "About Us" slide. Founder credibility goes in the deck only where relevant.
- Last slide is the ask, not a logo grid.

### B. One-pager

A single page (PDF or markdown) that captures the essence of the pitch for prospects to share internally.

Required sections:
1. **What we do** (1 sentence)
2. **Who it's for** (1 sentence — name the persona)
3. **The problem we solve** (2-3 sentences)
4. **How we're different** (3 bullets, each with a proof point)
5. **What customers see** (one outcome story or metric)
6. **What an engagement looks like** (1 paragraph — scope, time, deliverables)
7. **Pricing or commercial model** (1-2 sentences — at least a "starts at" or "tier ranges")
8. **Next step** (clear CTA, contact info)

Length: one page. Period. Two-pagers don't get forwarded.

### C. Demo script (founder-led)

A demo script is not a slide-by-slide narrator script. It's a structured outline of how the demo flows, what to show, and what to ask between sections.

Default structure (30-min demo):

| Minute | Section | What to do |
|---|---|---|
| 0-5 | Open + recap | Recap discovery; restate what you heard them say |
| 5-10 | Frame the demo | Set up what you'll show and why it's relevant to them specifically |
| 10-25 | Show + discuss | Live or recorded demo of 2-3 specific capabilities tied to their pain |
| 25-28 | Address obstacles | Surface objections before they surface them; address proactively |
| 28-30 | Define next step | Specific ask with timing |

Critical rules:
- **Don't demo what they didn't ask about.** Tour-style demos fail. Show only what's relevant to what they said in discovery.
- **Stop every 3-5 minutes for a check-in.** "Does this resonate?" or "Is this the kind of problem you're trying to solve?"
- **Demo specific use cases, not features.** Show how Bob would use the wedge to attract a prospect, not the dashboard navigation.

### D. Sales FAQ

Internal-facing document. Top 10-15 questions the founder gets asked, with the answer and the underlying logic.

Format:

```markdown
### Question: [The actual question, verbatim]

**Short answer:** [1-2 sentences, what to say in the call]

**Deeper answer:** [If the prospect pushes — extra context, specifics, evidence]

**What NOT to say:** [Common bad responses to avoid]

**Source/proof:** [Where the claim comes from]
```

Categories to cover:
- Product (what does it actually do?)
- Pricing (what does it cost? why?)
- Commercial model (how does engagement work?)
- Comparison (how is this different from X?)
- Stage/risk (you're pre-seed — what if you disappear?)
- Outcome (what should I expect?)
- Implementation (how long, who does what?)
- Compliance/security (especially for RIAs)

### E. Battlecard (per competitor)

One page per competitor. Used in real time on calls.

Format:

```markdown
# Battlecard: [Competitor]

**They are:** [1 sentence on what they actually do]
**Their positioning:** [Their own messaging in their words]
**Common context where prospects compare us:** [why this comes up]

## Where we win
1. [Differentiator] — [proof / specific evidence]
2. [Differentiator] — [proof]
3. [Differentiator] — [proof]

## Where they win (be honest)
1. [Their strength] — [how to handle it]
2. [Their strength] — [how to handle it]

## When prospect says: "We're already looking at [Competitor]"
**Don't say:** [Common bad response]
**Do say:** [Specific reframe — 2-3 sentences]

## When prospect says: "How are you different from [Competitor]?"
**Don't say:** [Common bad response]
**Do say:** [Specific reframe — 2-3 sentences, lead with their use case]

## Killer question to ask the prospect
[One question that exposes a weakness in the competitor's fit for this prospect]

## What NOT to claim
[Important guardrails — don't overclaim or trash-talk]
```

### F. Discovery question set

For first calls. Used by the founder to actually learn, not to lead the prospect to a yes.

Structured around four areas:

1. **Their world** (5 min)
   - "Walk me through what your week looks like."
   - "What's the biggest thing on your plate right now?"
   - "Who are you working with day-to-day?"

2. **The problem space** (10 min)
   - "When [problem we solve] comes up for you, what does that look like?"
   - "What have you tried? Why those things?"
   - "What's the cost of leaving this alone for 6 more months?"

3. **The decision dynamics** (10 min)
   - "If you decided to solve this, what would that process look like?"
   - "Who else would be involved? What would they care about?"
   - "What would make this NOT happen?"

4. **The close** (5 min)
   - "What would you need to see from us to take a next step?"
   - "What's your timing on this?"
   - "Is there anything I should have asked but didn't?"

Discovery is not a script. It's a structured conversation. Skip questions that don't fit; follow up when something surfaces.

### G. Proposal template

Sent after a demo, before close. Format:

```markdown
# Proposal: [Customer Name] + [Your Company]

**Date:** [date]
**Prepared for:** [name, role]
**Prepared by:** [your name]

## What we discussed
[2-3 sentences recapping the problem and the conversation. In their words, not yours.]

## What we propose
[1 paragraph: the specific engagement, scope, deliverables, timing]

## Why this approach
[2-3 sentences linking the proposal to what they said they needed]

## What's included
- [Specific deliverable 1]
- [Specific deliverable 2]
- [Specific deliverable 3]

## What's not included (out of scope)
[Important — sets expectations, prevents scope creep]

## Investment
[Specific pricing. Don't bury this — make it findable.]
[Payment terms if relevant]

## Success criteria
[How we'll know this worked — 2-3 specific outcomes]

## Timeline
[Specific dates for kickoff, key milestones, completion]

## What we need from you
[Specific list of inputs, access, or commitments needed from them]

## Next step
[Specific CTA — sign here, schedule kickoff, etc.]
```

Length: 1-2 pages. No filler. No legalese.

### H. Founder-led sales process (stage definitions)

For a founder to standardize their motion. Typical stages for a B2B founder-led sale (adapt to your sales cycle):

| Stage | Definition | Exit criterion | Typical duration |
|---|---|---|---|
| Identified | Prospect researched, on the outreach list | First message sent | — |
| Engaged | Prospect responded to outreach | Discovery call scheduled | 1-7 days |
| Discovered | Discovery call complete | Real qualification: problem + budget + timing confirmed | 1 call |
| Demo'd | Demo call complete | Proposal requested, or specific objection clear | 1 call |
| Proposed | Proposal sent | Verbal yes/no or specific blocker named | 3-14 days |
| Negotiating | Proposal accepted with changes | Final terms agreed | 1-7 days |
| Won | Contract/agreement signed | Kickoff scheduled | — |
| Lost | Deal dead | Loss reason captured | — |

Each stage has:
- A definition (when does it count?)
- An exit criterion (what has to be true to move?)
- A typical duration
- A "what we send/do in this stage" set of artifacts (drawn from above)

## Outputs

Based on what the user asked for. Common bundles:

**"Prep me for tomorrow's discovery call"** → Discovery question set + 1-pager + brief on the specific prospect + post-call follow-up template

**"Help me build the sales kit"** → 10-slide deck + one-pager + sales FAQ + 2-3 battlecards + proposal template

**"My demos are flat — help me fix"** → Demo script with specific structure + 3-5 demo do/don'ts + post-demo follow-up template

**"I keep getting [specific objection] — help"** → Updated battlecard or FAQ entry + 2-3 reframes + diagnostic on whether the objection signals a positioning problem (handoff to `positioning` skill)

## Quality bar

- **Specific over generic.** Every claim backed by a specific source. Every persona reference uses the actual persona's language.
- **Voice match.** Materials sound like the founder. Run the read-aloud test.
- **Honest about stage.** Pre-revenue is pre-revenue. Don't fake "trusted by industry leaders" when there's one design partner. Trust beats puffery.
- **Shorter is better.** 10-slide deck beats 30. 1-page proposal beats 4. Founder-led sales requires brevity.
- **Stage discipline.** Don't include closing materials in a discovery prep. Match the artifact to the moment.

## Anti-patterns to refuse

- Generating sales materials without a specific persona in mind
- Including claims not supported by `pmm-context.md` proof points
- 60-slide decks for founder-led conversations
- Generic objection responses ("Great question! Let me address that...") — must be specific
- Multi-page proposals for sub-$10K deals
- Sales process definitions without exit criteria
- Demoing features the prospect didn't ask about
- Skipping discovery to jump to demo
- Claiming "no competitors" or trash-talking real ones

## A note on tone

Founder-led sales has an unusual asset: the founder herself. Materials should feel like the founder talking, not a sales team. That means:

- First-person ("I built this because...") when appropriate
- Specific stories, not abstract claims
- Honesty about limitations ("we don't have SOC 2 yet — here's how we handle it")
- Confidence without arrogance
- Domain expertise visible in every sentence

The founder is the differentiator. The materials are scaffolding around them, not a replacement for them.

## Connection to other skills

- **`outreach`** — books the calls these materials support
- **`positioning`** — provides the strategic frame the pitch articulates
- **`personas`** — defines who you're selling to and in what language
- **`adaptive-messaging`** — when a competitor moves and battlecards need updating
- **`pmm-context`** — voice, proof points, and "what we don't do" guardrails for every artifact