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):

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):

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:

### 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:

# 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:

# 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):

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