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account-executive skill

/skills/account-executive

This skill provides strategic enterprise sales guidance for B2B SaaS, enabling multi-threading, deal progression, and land-and-expand planning to hit quota.

npx playbooks add skill ncklrs/startup-os-skills --skill account-executive

Review the files below or copy the command above to add this skill to your agents.

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SKILL.md
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---
name: account-executive
description: Expert full-cycle enterprise sales strategist for B2B SaaS. Use when planning sales strategy, pipeline management, deal progression, account planning, competitive displacement, or territory optimization. Covers multi-threading, executive engagement, champion development, buying committee navigation, and complex deal orchestration. Use for enterprise selling, account expansion, land-and-expand, and quota attainment.
---

# Account Executive

Strategic enterprise sales expertise for B2B SaaS companies — from pipeline building and deal progression to executive engagement and account expansion.

## Philosophy

Elite enterprise selling isn't about pitching features. It's about **becoming indispensable** to your champion's success.

The best enterprise AEs:
1. **Qualify ruthlessly, pursue relentlessly** — Time is your scarcest resource
2. **Multi-thread early and often** — Single-threaded deals die
3. **Sell outcomes, not products** — Features don't close deals, business impact does
4. **Control the process** — Mutual action plans beat hope
5. **Land with intent to expand** — Every deal is an account, not a transaction

## How This Skill Works

When invoked, apply the guidelines in `rules/` organized by:

- `pipeline-*` — Pipeline management, prioritization, forecasting
- `relationship-*` — Multi-threading, champion development, executive access
- `deal-*` — Deal progression, momentum, competitive displacement
- `account-*` — Account planning, expansion, land-and-expand
- `execution-*` — Time management, territory optimization, cadence

## Core Frameworks

### Deal Qualification (MEDDPICC)

| Element | Question | Red Flag |
|---------|----------|----------|
| **Metrics** | What business outcomes will success deliver? | No quantified value |
| **Economic Buyer** | Who signs the check? | Haven't met them |
| **Decision Criteria** | How will they decide? | Unknown or changing |
| **Decision Process** | What are the steps to close? | No clear timeline |
| **Paper Process** | Legal, procurement, security? | Unknown blockers |
| **Identified Pain** | What problem demands solving NOW? | Nice-to-have, not need |
| **Champion** | Who is selling internally for you? | No internal advocate |
| **Competition** | Who else is being evaluated? | Unknown alternatives |

### Deal Stages and Exit Criteria

```
┌─────────────────────────────────────────────────────────────────────────┐
│  DISCOVERY    │  SCOPING    │  VALIDATION  │  PROPOSAL   │  CLOSE     │
│     10%       │    25%      │     50%      │    75%      │   90%+     │
├───────────────┼─────────────┼──────────────┼─────────────┼────────────┤
│ Pain confirmed│ Solution    │ Technical    │ Commercial  │ Verbal     │
│ Champion ID'd │ requirements│ validation   │ terms       │ commitment │
│ Budget range  │ defined     │ complete     │ agreed      │ Legal/     │
│ Timeline set  │ Success     │ EB engaged   │ Proposal    │ procurement│
│               │ criteria    │ ROI accepted │ delivered   │ complete   │
└───────────────┴─────────────┴──────────────┴─────────────┴────────────┘
```

### The Buying Committee

```
                    ┌──────────────────┐
                    │  ECONOMIC BUYER  │
                    │  (Signs check)   │
                    └────────┬─────────┘
                             │
         ┌───────────────────┼───────────────────┐
         │                   │                   │
    ┌────▼────┐        ┌─────▼─────┐       ┌────▼────┐
    │TECHNICAL│        │  CHAMPION │       │ USER    │
    │  BUYER  │        │ (Your     │       │ BUYER   │
    │(IT/Sec) │        │  advocate)│       │(End user│
    └─────────┘        └───────────┘       │ leader) │
                                           └─────────┘
                    ┌──────────────────┐
                    │   INFLUENCERS    │
                    │ (Consultants,    │
                    │  Peers, Legal)   │
                    └──────────────────┘
```

### Account Tiering

| Tier | Characteristics | Time Investment | Strategy |
|------|-----------------|-----------------|----------|
| **Tier 1** | $100k+ potential, strategic fit, active buying | 40% of time | White-glove, executive-sponsored |
| **Tier 2** | $50-100k potential, good fit, developing need | 35% of time | High-touch, multi-threaded |
| **Tier 3** | $25-50k potential, fit confirmed, timeline unclear | 20% of time | Efficient, templated |
| **Tier 4** | <$25k or poor fit | 5% of time | Automated, self-serve, or disqualify |

### Pipeline Math

```
Target: $1M Annual Quota
Average Deal Size: $50K
Win Rate: 25%
Average Sales Cycle: 90 days

Required:
- Closed Won: 20 deals/year
- Pipeline Coverage: 4x = $4M active pipeline
- Opportunities/Quarter: 20 new opps
- Meetings/Week: ~8 qualified meetings

Pipeline Coverage by Stage:
- Discovery (10%): 40% of coverage
- Scoping (25%): 25% of coverage
- Validation (50%): 20% of coverage
- Proposal (75%): 10% of coverage
- Closing (90%): 5% of coverage
```

### Competitive Positioning

| Situation | Strategy | Risk |
|-----------|----------|------|
| **Incumbent** | Land-and-expand, proof of value, executive alignment | Complacency, disruption |
| **Challenger** | Differentiation, champion mobilization, urgency creation | Longer sales cycle |
| **Unknown** | Early discovery, pain quantification, category creation | Education burden |
| **Displacing competitor** | FUD (Fear, Uncertainty, Doubt), cost of status quo, migration support | Resistance to change |

## Deal Momentum Indicators

### Positive Signals

- Champion proactively schedules next meeting
- Economic buyer agrees to attend presentation
- Customer shares internal documents/org charts
- Technical team asks detailed implementation questions
- Procurement timeline communicated
- Reference calls requested
- Legal/security review initiated

### Danger Signals

- Meetings rescheduled or cancelled
- New stakeholders introduced late
- "Let me run this by..." with no follow-up
- Competitor mentioned after you thought you'd won
- Budget concerns raised after proposal
- Champion goes dark
- "We'll get back to you" without date

## Anti-Patterns

- **Happy ears** — Hearing what you want, ignoring red flags
- **Single-threading** — Relying on one contact who leaves or loses influence
- **Feature dumping** — Presenting capabilities without connecting to outcomes
- **Proposal too early** — Sending pricing before value is established
- **Hoping vs. controlling** — No mutual action plan, just waiting
- **Demo before discovery** — Showing product without understanding needs
- **Ignoring competition** — Assuming you're the only option
- **Neglecting champions** — Not enabling them to sell internally
- **Forecast fantasy** — Committing deals that aren't real
- **Post-close abandonment** — Moving on without ensuring success for expansion

Overview

This skill is an expert full-cycle enterprise sales strategist for B2B SaaS. It provides pragmatic frameworks and tactical guidance for pipeline building, deal progression, account planning, and territory optimization. Use it to convert complex enterprise opportunities into predictable wins and scalable expansions.

How this skill works

When invoked, the skill applies structured rules across pipeline, relationship, deal, account, and execution domains. It operationalizes MEDDPICC qualification, stage-based exit criteria, buying-committee mapping, pipeline math, and competitive playbooks. Outputs include prioritized actions, mutual action plans, risk flags, and cadence recommendations to drive momentum and forecast accuracy.

When to use it

  • Designing territory coverage and time allocation across accounts
  • Qualifying and prioritizing opportunities using MEDDPICC
  • Building multi-threaded engagement plans and executive access strategies
  • Displacing incumbents or positioning versus competitors
  • Creating account plans for land-and-expand and expansion motions
  • Forecasting and optimizing pipeline coverage to hit quota

Best practices

  • Qualify ruthlessly: eliminate low-probability deals early to focus time
  • Multi-thread early: identify champion, economic buyer, technical and user buyers
  • Sell outcomes: tie every conversation to quantified business impact
  • Control the process: build mutual action plans with clear owners and timelines
  • Tier accounts and time: white-glove for Tier 1, automated for Tier 4
  • Monitor momentum signals and act on danger signs immediately

Example use cases

  • Assess a 90-day pipeline and recommend coverage to meet quarterly quota
  • Audit a stalled opportunity and produce a reactivation plan with new stakeholders and urgency plays
  • Create an account playbook for a strategic Tier 1 customer with expansion milestones
  • Build a competitive displacement strategy tailored to incumbent, challenger, or unknown scenarios
  • Design weekly cadences and meeting goals to generate required qualified meetings per week

FAQ

How does MEDDPICC fit into day-to-day activity?

Use MEDDPICC as a checklist when qualifying and updating opportunities; require at least metrics, economic buyer, champion, and timeline before allocating major time.

When should I disqualify an opportunity?

Disqualify when pain is not urgent, economic buyer is unknown or unreachable, or timeline and budget are absent after repeated discovery.