SKILL.md
Sales Enablement
Strategic sales enablement expertise for building world-class sales organizations — from onboarding to continuous development.
Philosophy
Great sales enablement isn't about training events. It's about creating systems that compound seller effectiveness over time.
The best enablement programs:
- Reduce time-to-productivity — Every day of ramp time costs revenue
- Enable, don't dictate — Provide tools and frameworks, not scripts
- Measure outcomes, not activities — Training hours mean nothing without behavior change
- Meet sellers where they are — Just-in-time beats just-in-case
How This Skill Works
When invoked, apply the guidelines in rules/ organized by:
training-* — Training program design, delivery, retention
onboarding-* — New hire ramp, bootcamps, 30-60-90 plans
playbook-* — Sales playbook creation, maintenance, adoption
content-* — Enablement content strategy and management
coaching-* — Coaching programs, feedback systems, skill development
certification-* — Certification design, assessment, compliance
tools-* — Tool adoption, training, stack optimization
measurement-* — Metrics, ROI, performance tracking
Core Frameworks
The Enablement Maturity Model
| Stage |
Characteristics |
Focus |
| Ad Hoc |
Reactive, tribal knowledge |
Document what exists |
| Foundational |
Basic onboarding, scattered content |
Build core programs |
| Managed |
Consistent programs, basic metrics |
Measure and iterate |
| Optimized |
Data-driven, personalized paths |
Predictive enablement |
| Strategic |
Revenue attribution, business partner |
Enablement as competitive advantage |
The 70-20-10 Learning Model
┌─────────────────┐
│ Experiential │ ← 70% — Learning by doing
│ (On the job) │ Deals, calls, shadowing
├─────────────────┤
│ Social │ ← 20% — Learning from others
│ (Coaching) │ Mentors, peers, feedback
├─────────────────┤
│ Formal │ ← 10% — Structured training
│ (Training) │ Courses, certifications
└─────────────────┘
Enablement Content Types
| Content Type |
Purpose |
When to Use |
Shelf Life |
| Playbooks |
Process guidance |
Complex deals, new motions |
6-12 months |
| Battle Cards |
Competitive positioning |
Head-to-head deals |
3-6 months |
| Talk Tracks |
Conversation starters |
Discovery, objections |
6-12 months |
| Case Studies |
Proof points |
Late-stage deals |
12-24 months |
| Quick Reference |
Just-in-time help |
Daily selling |
Ongoing updates |
| Micro-learning |
Skill reinforcement |
Continuous development |
6-12 months |
The Ramp Timeline
Week 1-2: FOUNDATIONS
├── Company, product, market
├── Tools and systems
└── Shadow experienced reps
Week 3-4: SKILLS BUILDING
├── Methodology training
├── Product deep-dives
└── Role-play practice
Week 5-8: GUIDED PRACTICE
├── Assisted customer calls
├── Deal coaching
└── First solo activities
Week 9-12: INDEPENDENT PERFORMANCE
├── Full territory ownership
├── Performance to quota
└── Certification completion
Seller Competency Framework
┌─────────────────────────────────────────────────────────────┐
│ BUSINESS ACUMEN │
│ (Industry, market, financial understanding) │
├─────────────────────────────────────────────────────────────┤
│ PRODUCT KNOWLEDGE SALES SKILLS │
│ (Features, use cases, (Discovery, demo, │
│ competition) negotiation) │
├─────────────────────────────────────────────────────────────┤
│ TOOL PROFICIENCY │
│ (CRM, enablement platform, sales tools) │
└─────────────────────────────────────────────────────────────┘
Program Overview
| Program |
Audience |
Cadence |
Owner |
| New Hire Bootcamp |
All new sales hires |
Continuous |
Enablement |
| Product Release Training |
All sellers |
Per release |
Product + Enablement |
| Methodology Reinforcement |
All sellers |
Quarterly |
Enablement |
| Competitive Updates |
All sellers |
Monthly |
Competitive Intel |
| SKO (Sales Kickoff) |
All revenue team |
Annual |
Enablement + Leadership |
| Manager Coaching |
Frontline managers |
Monthly |
Enablement |
| Role Certifications |
By role |
Annual |
Enablement |
Anti-Patterns
- Training events as strategy — One-time training doesn't change behavior
- Content graveyards — Building content no one uses or can find
- Product feature focus — Teaching features instead of customer outcomes
- Enablement as admin — Scheduling training instead of driving performance
- One-size-fits-all — Same training for enterprise AE and SMB SDR
- No measurement — Can't prove impact, can't get resources
- Tribal knowledge — Top performers hoard instead of share
- Tool overload — Adding tools without removing friction