# Sales Enablement Director Playbook

Reference playbook for the sales-enablement-director skill. Read the relevant section before producing any enablement artifact.

## Table of Contents

1. Enablement Program Design
2. Onboarding Curriculum - Detailed Build Guide
3. Certification Design and Rubrics
4. Discovery Methodology Training
5. Demo Methodology Training
6. Competitive Intelligence Program
7. Win/Loss Analysis Protocol
8. Deal Inspection and Pipeline Coaching
9. Ongoing Enablement Cadence
10. Sales Content Management
11. Measuring Enablement Impact

---

## 1. Enablement Program Design

### The Enablement Architecture

Effective enablement has four interconnected layers:

```
LAYER 1: KNOWLEDGE (What reps need to know)
  - Product, market, ICP, personas, competitors, methodology
  - Delivered through: Onboarding, documentation, knowledge base
  - Measured by: Certification scores, knowledge assessments

LAYER 2: SKILLS (What reps need to do)
  - Discovery, demo, negotiation, objection handling, multi-threading
  - Delivered through: Workshops, role-plays, coaching, practice
  - Measured by: Call scores, certification, manager assessment

LAYER 3: TOOLS (What reps need to use)
  - Battle cards, talk tracks, templates, calculators, content
  - Delivered through: Content platform, CRM, sequence tools
  - Measured by: Usage rates, content effectiveness, time-to-find

LAYER 4: REINFORCEMENT (What makes it stick)
  - Coaching, peer learning, practice, spaced repetition
  - Delivered through: 1:1s, deal reviews, workshops, competitions
  - Measured by: Behavior change over time, sustained metric improvement
```

### Enablement Needs Assessment

Before building any program, diagnose what's actually needed:

**Data analysis:**
- Ramp time (days to first deal, days to full quota)
- Win rates by rep tenure (do experienced reps win more?)
- Stage conversion rates (where do deals stall?)
- Competitive win/loss rates (do we lose to specific competitors?)
- Average deal size by rep (are some consistently underselling?)

**Field observation:**
- Shadow 5-10 calls across the team
- Score each call on: discovery depth, messaging accuracy, objection handling, next step quality
- Identify patterns: what are most reps doing well? Where do most struggle?

**Rep survey (anonymous):**
- "What's the #1 thing you wish you knew when you started?"
- "Where do you feel least confident in sales conversations?"
- "What competitive situation is hardest to navigate?"
- "What content do you wish you had?"
- "Rate your confidence: discovery, demo, negotiation, competitive, executive conversations"

**Manager input:**
- "Where do your reps struggle most?"
- "What deals are you losing and why?"
- "What takes the longest during onboarding?"
- "What training would have the most impact?"

---

## 2. Onboarding Curriculum - Detailed Build Guide

### Week 1: Company and Market Foundation

| Day | Topic | Format | Owner | Deliverable |
|-----|-------|--------|-------|-------------|
| Mon | Company mission, values, org structure | Presentation + Q&A | CEO or CRO | Org chart with key contacts |
| Mon | Product overview - what it does, who uses it, how it works | Product demo + sandbox access | Product/SE team | Sandbox environment setup |
| Tue | Market landscape: category, trends, competitive overview | Presentation + discussion | Product Marketing | Competitive landscape doc |
| Tue | ICP deep dive: segments, personas, trigger events | Workshop | Sales Enablement | ICP reference card |
| Wed | Customer journey: how buyers find, evaluate, and buy | Presentation | Marketing + Sales | Funnel stage definitions |
| Wed | Listen to 5 recorded discovery calls (annotated) | Self-study + debrief | Manager | Call analysis notes |
| Thu | CRM setup and sales process walkthrough | Hands-on workshop | RevOps | CRM configured, process doc |
| Thu | Tools training: sequence tool, LinkedIn Sales Nav, enrichment | Hands-on workshop | RevOps | Tools configured |
| Fri | Week 1 knowledge check (quiz) | Assessment | Enablement | Score + gaps identified |

### Week 2: Product and Competitive Deep Dive

| Day | Topic | Format | Owner | Deliverable |
|-----|-------|--------|-------|-------------|
| Mon | Product deep dive #1: core use case and workflow | Live demo + hands-on | SE team | Can navigate core product |
| Tue | Product deep dive #2: enterprise features and differentiation | Live demo + hands-on | SE team | Can describe enterprise value |
| Wed | Competitive deep dive #1: Primary competitor | Workshop | Product Marketing | Battle card familiarity |
| Wed | Competitive deep dive #2: Secondary competitors | Workshop | Product Marketing | Battle card familiarity |
| Thu | Pricing and packaging: how deals are structured | Presentation + examples | Sales leader | Pricing reference card |
| Thu | Legal/procurement process: how contracts work | Presentation | Legal/Deal Desk | Process doc |
| Fri | Product knowledge certification (first attempt) | Certification | Manager + Enablement | Pass/fail + remediation |

### Week 3: Methodology and Practice

| Day | Topic | Format | Owner | Deliverable |
|-----|-------|--------|-------|-------------|
| Mon | Discovery methodology: MEDDIC framework + company-specific adaptation | Workshop | Enablement | Discovery question bank |
| Mon | Role-play: Discovery call (5 rounds, increasing difficulty) | Practice | Manager + peers | Recorded for review |
| Tue | Demo methodology: needs-based demo, not feature tour | Workshop | SE team | Demo flow framework |
| Tue | Role-play: Demo delivery (3 rounds, different personas) | Practice | Manager + SE | Recorded for review |
| Wed | Objection handling: top 15 objections with response frameworks | Workshop | Enablement | Objection response card |
| Wed | Role-play: Objection handling gauntlet (rapid-fire) | Practice | Team | Confidence assessment |
| Thu | Email and outreach: templates, personalization, follow-up | Workshop | SDR manager | Template library access |
| Thu | Write 5 prospecting emails, get feedback | Practice | Manager | Revised emails |
| Fri | Shadow live calls with experienced AE (3-5 calls) | Observation | Peer AE | Shadow notes |

### Week 4: Live Practice with Guardrails

| Day | Topic | Format | Owner | Deliverable |
|-----|-------|--------|-------|-------------|
| Mon-Tue | Run first live discovery calls (manager on the line, muted) | Live calls | New hire + manager | Call recordings + debrief |
| Wed | Pitch certification attempt | Certification | Panel | Pass/fail |
| Thu-Fri | Continue live calls with decreasing manager involvement | Live calls | New hire | Pipeline activity begun |

### Month 2-3: See ramp schedule in SKILL.md

### Onboarding Measurement

Track these metrics to evaluate onboarding effectiveness:

| Metric | Target | When to Measure |
|--------|--------|-----------------|
| Days to first meeting booked | <14 days | End of month 1 |
| Days to first opportunity created | <30 days | End of month 1 |
| Days to first deal closed | <90 days | End of month 3 |
| Product certification pass rate (first attempt) | >80% | End of week 2 |
| Pitch certification pass rate (first attempt) | >70% | End of week 4 |
| Ramp quota attainment (month 3) | >50% | End of month 3 |
| Full quota attainment (month 6) | >70% | End of month 6 |
| New hire satisfaction (survey) | >4/5 | End of month 1 and 3 |
| Manager satisfaction with hire readiness | >4/5 | End of month 3 |

---

## 3. Certification Design and Rubrics

### Certification Rubric Template

Use this template for any certification (pitch, demo, discovery, competitive):

```
CERTIFICATION: [Name]
EVALUATOR(S): [Names/roles]
REP: ___________________    DATE: ____________

DIMENSIONS (score each 1-4):

1. CONTENT ACCURACY                                    [ ]
   1 = Significant inaccuracies or missing key points
   2 = Mostly accurate with minor gaps
   3 = Accurate and complete
   4 = Accurate, complete, and adds nuance

2. PERSONA RELEVANCE                                   [ ]
   1 = Generic, not tailored to audience
   2 = Some tailoring but misses key persona concerns
   3 = Well-tailored to the persona's goals and fears
   4 = Deeply personalized; buyer feels understood

3. STRUCTURE AND FLOW                                  [ ]
   1 = Disorganized, hard to follow
   2 = Basic structure but transitions are rough
   3 = Clear structure with logical flow
   4 = Compelling narrative arc that builds to action

4. OBJECTION HANDLING                                  [ ]
   1 = Stumped by basic objections
   2 = Handles common objections with scripted responses
   3 = Handles objections naturally, addresses underlying concern
   4 = Turns objections into selling opportunities

5. CONFIDENCE AND PRESENCE                             [ ]
   1 = Uncertain, reads from notes, lacks conviction
   2 = Generally confident but falters under pressure
   3 = Confident and natural throughout
   4 = Commanding presence; builds trust immediately

6. NEXT STEP / CLOSE                                   [ ]
   1 = No clear ask or next step proposed
   2 = Asks for next step but vaguely
   3 = Proposes specific, logical next step with timeline
   4 = Creates urgency and commitment; buyer is eager

TOTAL: [ ] / 24

PASS: 18+ with no dimension below 2
CONDITIONAL PASS: 15-17 (remediation on weak areas, retest in 1 week)
FAIL: <15 (retraining required, retest in 2 weeks)

STRENGTHS:
_______________________________________________

DEVELOPMENT AREAS:
_______________________________________________

SPECIFIC FEEDBACK:
_______________________________________________
```

### Certification Best Practices

- Announce the persona in advance (rep should prepare for that buyer)
- Evaluator plays a realistic buyer (not adversarial, but not easy)
- Record every certification for the rep to self-review
- Provide written feedback within 24 hours
- Failed certifications are not punitive - they're development opportunities
- Recertify every 6 months (messaging evolves, skills drift)

---

## 4. Discovery Methodology Training

### The Discovery Framework

Discovery is the highest-leverage skill in enterprise sales. A great discovery call creates the conditions for everything that follows.

**The Discovery Pyramid:**

```
                    /\
                   /  \
                  / IM \        IMPACT: "What's the business cost?"
                 / PACT \       Quantify the pain in metrics leadership cares about
                /________\
               /          \
              /  IMPLICA-  \    IMPLICATIONS: "What happens if you don't fix this?"
             /    TIONS     \   Explore consequences of inaction
            /______________\
           /                \
          /    SITUATION     \   SITUATION: "What's happening today?"
         /    & PROBLEM      \  Understand current state and specific pain
        /____________________\

Move UP the pyramid during discovery. Most reps stay at the bottom
(asking about the situation) and never reach the top (quantifying impact).
The top of the pyramid is where urgency and budget justification live.
```

### Discovery Question Bank (Enterprise B2B)

**Situation Questions (establish context):**
- "Walk me through how your team handles [area] today."
- "What tools are you currently using for [function]?"
- "How is your team structured? Who's involved in [area]?"
- "How long have you been using [current approach]?"

**Problem Questions (identify pain):**
- "What's the biggest challenge with your current setup?"
- "Where does the current approach fall short?"
- "What triggered you to start looking at alternatives?"
- "If you could change one thing, what would it be?"

**Implication Questions (explore consequences):**
- "What happens when [problem] occurs? What's the downstream impact?"
- "How does [problem] affect your team's ability to [goal]?"
- "When [problem] last happened, what did that cost in time/money/risk?"
- "How does [problem] affect your standing with leadership/auditors/board?"

**Impact Questions (quantify value):**
- "If [problem] were solved, what would that mean in terms of [their metric]?"
- "What would it be worth to [specific outcome] within [timeframe]?"
- "How would solving this change your team's capacity/focus/risk profile?"
- "What would [executive stakeholder] say if you could show [improvement]?"

**Process Questions (map the buying journey):**
- "Who else would need to be involved in evaluating a solution?"
- "What does the decision process typically look like for something like this?"
- "Is there a timeline or event driving this?"
- "How are initiatives like this typically funded?"

### Discovery Anti-Patterns to Train Against

| Anti-Pattern | What It Looks Like | Why It Fails | The Fix |
|-------------|-------------------|--------------|---------|
| Feature dumping | Rep talks about product before understanding the problem | Buyer checks out; no connection to their pain | Rule: No product discussion in first 20 minutes |
| Interrogation | Rapid-fire questions with no acknowledgment | Buyer feels like a suspect, not a partner | Acknowledge every answer before the next question |
| Surface discovery | "What are your challenges?" → one answer → move to demo | Misses the real pain (often 2-3 layers deep) | Follow up 3x: "Tell me more," "Why is that?," "What's the impact?" |
| Premature solution | "Oh, we can fix that!" (at first mention of pain) | Kills deeper discovery; buyer thinks problem is simple | Wait. Explore fully. Then connect solution to the full picture. |
| Single-thread | Only talk to one person | Miss the full buying committee and politics | Always ask: "Who else sees this problem? Who else would benefit?" |

---

## 5. Demo Methodology Training

### The Needs-Based Demo Framework

A demo is not a product tour. It's a conversation where the product proves the claims made during discovery.

```
STRUCTURE:

1. RECAP DISCOVERY (2 min)
   "Last time we spoke, you mentioned [pain 1], [pain 2], and [pain 3].
    You said the biggest impact was [quantified impact]. Is that still accurate?"
   WHY: Reconnects to their pain. Confirms nothing has changed. Reestablishes urgency.

2. AGENDA & PERMISSION (1 min)
   "What I'd like to do is show you three things that address those specific
    challenges. Should take about 20 minutes, then we can discuss. Sound good?"
   WHY: Sets expectations. Prevents the demo from running off the rails.

3. SHOW → TELL → ASK (15-20 min, repeat for each pain point)
   SHOW: Demonstrate the capability that addresses their specific pain
   TELL: "What this means for your team is [outcome in their language]"
   ASK: "How does that compare to how you handle this today?"
   WHY: Each cycle connects product to their pain, then checks for resonance.

4. SOCIAL PROOF ANCHOR (2 min)
   "[Company like theirs] was in a similar situation. They saw [result] within
    [timeframe]. Their [persona] said [quote]."
   WHY: Moves from "this is what it does" to "this is what it did for someone like you."

5. CLOSE TO NEXT STEP (5 min)
   "Based on what you've seen, what questions do you have?"
   [Handle questions]
   "The logical next step would be [specific action]. How does [date/time] look?"
   WHY: Tests buying temperature and advances the deal.
```

### Demo Anti-Patterns

| Anti-Pattern | Fix |
|-------------|-----|
| The Feature Tour: Showing everything the product does | Only show capabilities that map to validated pain points |
| The Happy Path Only: Everything works perfectly, no real-world scenarios | Show the messy reality - troubleshooting, edge cases, error handling |
| The Monologue: Rep talks for 30 minutes straight | Stop every 5-7 minutes: "How does that resonate?" |
| The Kitchen Sink: Demo runs 60+ minutes | Target 20-25 minutes of showing. Discovery already happened. |
| The Unsupported Claim: "It's super easy to set up!" | Show the setup. Let the product speak for itself. |

---

## 6. Competitive Intelligence Program

### Building a CI Function

**Intelligence Sources (establish all of these):**

| Source | Cadence | Owner | Output |
|--------|---------|-------|--------|
| Win/loss interviews | Every closed deal >$50K | Sales Enablement | Win/loss database |
| AE field intel submissions | Continuous (Slack channel or form) | All AEs | Field intel feed |
| Competitor website/product monitoring | Weekly | Product Marketing | Change log |
| G2/TrustRadius review monitoring | Biweekly | Product Marketing | Review digest |
| Job posting analysis | Monthly | Product Marketing | Strategic direction report |
| Analyst reports | As published | Product Marketing | Summary + implications |
| Community monitoring | Continuous | DevRel/Community | Signal feed |
| Customer advisory board | Quarterly | CS/Product | Competitive perception |

**CI Distribution:**

| Audience | Format | Cadence |
|----------|--------|---------|
| AEs | Battle card updates, Slack alerts for major changes | Real-time for alerts, monthly for battle cards |
| SDRs | Competitive talk track updates, displacement trigger alerts | Monthly |
| Leadership | Competitive landscape report, win/loss patterns | Quarterly |
| Product | Feature gap analysis, competitive feature tracking | Monthly |

---

## 7. Win/Loss Analysis Protocol

### Interview Process

**Who to interview:**
- The champion or primary contact (always)
- The economic buyer (when possible)
- The technical evaluator (for competitive losses)
- Your AE (before the customer interview, for context)

**When to interview:**
- Within 2 weeks of deal close (win or loss)
- Memory fades fast - 30 days out and you get rationalized answers, not real ones

**Interview Guide (Customer):**

```
OPENING:
"Thank you for your time. I'm on our [enablement/strategy] team, not sales,
so I'd love your candid perspective. This helps us improve, regardless of
the outcome."

BUYING PROCESS:
- "What initially triggered you to start looking for a solution?"
- "Who was involved in the evaluation? How did each person influence the decision?"
- "What were your top 3 evaluation criteria?"

COMPETITIVE:
- "What other options did you consider?"
- "What were the key differences between us and [competitor]?"
- "Was there a moment when one option started pulling ahead?"

FOR WINS:
- "What ultimately tipped the decision in our favor?"
- "Was there anything that almost made you choose differently?"
- "What could we have done better during the process?"

FOR LOSSES:
- "What ultimately drove the decision to go with [competitor/status quo]?"
- "Was there a specific moment where we fell behind?"
- "What could we have done differently?"
- "Would you consider us for future needs? What would change your mind?"

CLOSE:
- "Any advice for our team when working with companies like yours?"
- "Is there anything I didn't ask that you think we should know?"
```

### Win/Loss Analysis Template

```
DEAL: [Company name]    OUTCOME: Win / Loss
ACV: $___              CYCLE LENGTH: ___ days
COMPETITOR(S): ______   SEGMENT: _______________

PRIMARY WIN/LOSS REASON:
[1-2 sentences - the real reason, not the CRM dropdown]

CONTRIBUTING FACTORS:
- [Factor 1]
- [Factor 2]
- [Factor 3]

BUYING COMMITTEE:
- [Name, Title, Role in deal, Sentiment (positive/neutral/negative)]

WHAT WE DID WELL:
- [Specific action that helped]

WHAT WE COULD IMPROVE:
- [Specific action that hurt or was missing]

COMPETITIVE INSIGHT:
[What we learned about the competitor from this deal]

PATTERN TAG:
[Tag for aggregation: pricing, product gap, competitive, process, champion, timing]
```

### Quarterly Win/Loss Review

Aggregate individual analyses into patterns:

```
Q[X] WIN/LOSS REVIEW

DEALS ANALYZED: ___ wins, ___ losses

TOP WIN REASONS (ranked by frequency):
1. [Reason] - cited in __% of wins
2. [Reason] - cited in __% of wins
3. [Reason] - cited in __% of wins

TOP LOSS REASONS (ranked by frequency):
1. [Reason] - cited in __% of losses
2. [Reason] - cited in __% of losses
3. [Reason] - cited in __% of losses

COMPETITIVE PATTERNS:
- vs. [Competitor A]: Won __/__, primarily because [pattern]
- vs. [Competitor B]: Won __/__, primarily because [pattern]

ACTIONABLE RECOMMENDATIONS:
1. [Action] - addresses [loss reason]. Owner: [name]. Due: [date].
2. [Action] - reinforces [win reason]. Owner: [name]. Due: [date].
3. [Action] - addresses [competitive gap]. Owner: [name]. Due: [date].
```

---

## 8. Deal Inspection and Pipeline Coaching

### The FORCE Deal Inspection Framework

For each deal in pipeline review, evaluate five dimensions:

```
F - FIT: Does this account match our ICP?
  - Firmographic fit (size, industry, tech stack)
  - Behavioral fit (they're experiencing our target trigger events)
  - Red flag: No ICP match = remove from pipeline

O - OPPORTUNITY: Is there a real, funded opportunity?
  - Validated pain with business impact quantified
  - Budget identified or path to budget clear
  - Timeline driven by a compelling event
  - Red flag: No compelling event = deal will stall

R - RELATIONSHIPS: Do we have the right access?
  - Champion identified and engaged (not just friendly - actively selling internally)
  - Economic buyer identified and at least aware
  - Technical evaluator engaged
  - Red flag: Single-threaded to one contact = high risk

C - COMPETITION: Are we positioned to win?
  - We know who else is being evaluated
  - We've set landmines and differentiated
  - Our champion can articulate why us vs. alternatives
  - Red flag: No competitive intelligence = flying blind

E - EXECUTION: Is the deal progressing?
  - Mutually agreed next steps with dates
  - Prospect is doing work between meetings (key signal)
  - CRM is updated and accurate
  - Red flag: No next step or prospect going dark = stall
```

### Coaching Conversation Framework

```
SITUATION (manager asks, rep explains):
"Walk me through this deal. Where are we?"

ASSESSMENT (manager probes):
"What's the biggest risk in this deal right now?"
"Who on the buying committee have we NOT talked to?"
"What does the champion say when you're not in the room?"

OPTIONS (manager helps rep think):
"What are your options for [addressing the risk]?"
"What would you do if [worst case scenario]?"
"Who could help us get access to [stakeholder]?"

COMMITMENT (rep decides, manager validates):
"What are you going to do by [date]?"
"What do you need from me to make that happen?"

FOLLOW-UP:
"I'll check in on [date] to see how [action] went."
```

---

## 9. Ongoing Enablement Cadence

### Monthly Enablement Planning Template

```
MONTH: [Month/Year]

THEME: [Focus area for the month - e.g., "Competitive Selling" or "Executive Engagement"]

WEEKLY SESSIONS:
  Week 1: [Topic] - [Format] - [Owner] - [Duration]
  Week 2: [Topic] - [Format] - [Owner] - [Duration]
  Week 3: [Topic] - [Format] - [Owner] - [Duration]
  Week 4: [Topic] - [Format] - [Owner] - [Duration]

CONTENT RELEASES:
  - [New/updated asset] - [Date] - [Distribution channel]

CERTIFICATIONS:
  - [Any scheduled recertifications or new certifications]

MEASUREMENT:
  - [What we'll track to know if this month's enablement worked]
```

---

## 10. Sales Content Management

### Content Governance

**Content lifecycle:**

| Stage | Action | Owner | Cadence |
|-------|--------|-------|---------|
| Create | Build new content against content brief | Content creator | As needed |
| Review | Product marketing validates accuracy and messaging | Product Marketing | Before publish |
| Publish | Add to content platform with metadata (persona, stage, use case) | Enablement | Same day |
| Train | Introduce to sales team with context on when/how to use | Enablement | Within 1 week |
| Measure | Track usage and deal correlation | RevOps | Monthly |
| Refresh | Update based on market changes, product updates, feedback | Product Marketing | Quarterly |
| Retire | Remove outdated content, redirect to current version | Enablement | Quarterly |

### Content Findability

The best content is useless if reps can't find it in 30 seconds. Organize by:
- Persona (who is the buyer?)
- Stage (where are they in the process?)
- Use case (what problem are they solving?)
- Competitor (if competitive content)

---

## 11. Measuring Enablement Impact

### Enablement Metrics Dashboard

| Metric | What It Tells You | Target |
|--------|-------------------|--------|
| Time to first deal | Is onboarding effective? | <90 days |
| Ramp to full quota | Are reps getting productive? | <6 months |
| Certification pass rate (first attempt) | Is training sufficient? | >75% |
| Win rate (all deals) | Is the team getting better? | Improving QoQ |
| Competitive win rate | Are battle cards working? | >50% vs. each competitor |
| Average deal size | Are reps selling value? | Stable or increasing |
| Sales cycle length | Are reps running efficient processes? | Stable or decreasing |
| Content usage rate | Is content being used? | >60% of assets used monthly |
| New hire NPS | Do new hires feel supported? | >40 |
| Manager coaching hours | Is coaching happening? | >2 hrs/rep/month |
