SimonTheSalesBooster Skill: Enterprise B2B Deal Hunter
What This Skill Does
Builds a complete strategy for landing large B2B enterprise deals — identifying the right targets, mapping the buying committee, designing the account approach, and building the multi-threaded relationship network needed to close high-value, complex deals. Designed for deals above $100K where 3+ stakeholders are involved and sales cycles run 3–12 months.
When to Use
- You're going upmarket and want to land your first or next enterprise account
- You've been stuck at SMB/mid-market and want to understand how enterprise selling is different
- A large company has shown interest and you need a plan to work the account
- You want to build an enterprise pipeline from scratch in a defined target account list
- Your deal is complex, multi-stakeholder, and you need to orchestrate the process
Inputs Required
Before running this skill, ask the user for:
- Target company (or type of target company) — name, industry, size, known contacts
- Your solution — what you sell and why enterprise companies need it
- Ideal deal size — what does a successful enterprise deal look like for you?
- Current status — prospecting stage, or already in conversation?
- What you know about the account — any contacts, history, or intel already gathered?
Step-by-Step Instructions
Step 1 — Enterprise Account Selection
Not every large company is a good enterprise target. Score target accounts on:
Enterprise Account Scoring Rubric:
| Criteria | Score (1–3) |
|---------------------------------------|------------|
| Fits ICP (industry, size, model) | |
| Evidence of the problem you solve | |
| Budget signals (funded, growing) | |
| Inbound signals (visited site, etc.) | |
| Warm path in (connection, referral) | |
| Competitive landscape favorable | |
| Geographic fit | |
| Strategic value (logo, reference) | |
Score 18–24 = Tier 1 — invest heavily Score 12–17 = Tier 2 — develop and track Below 12 = Deprioritize
Step 2 — Map the Buying Committee
Enterprise deals involve multiple stakeholders. Identify and map each role:
The 6 Buying Committee Roles:
1. CHAMPION — Your internal advocate who sells for you
Goal: Enable them with everything they need to advocate
Risk: They're not senior enough or influential enough alone
2. ECONOMIC BUYER — Controls the budget and signs the check
Goal: Get direct access early. Quantify ROI in their language.
Risk: Never meeting them until end = deals die in procurement
3. END USER — Uses your product day-to-day
Goal: Create enthusiasm and desire. They influence the champion.
Risk: If users don't want it, nothing else matters
4. TECHNICAL EVALUATOR — Assesses security, integration, infrastructure
Goal: Pass their evaluation cleanly and early
Risk: Late-stage technical blockers that kill momentum
5. PROCUREMENT / LEGAL — Controls the contract process
Goal: Understand their process before you get there
Risk: Surprise requirements that delay or kill signed deals
6. EXECUTIVE SPONSOR / BOARD — May have a stake in strategic decisions
Goal: Awareness and indirect influence
Risk: Not relevant in all deals — use judgment
Account Map Template:
| Role | Name | Title | Sentiment | Engaged? | Priority Action |
|-------------------|---------|-------|-----------|----------|----------------|
| Champion | | | +/=/− | Y/N | |
| Economic Buyer | | | +/=/− | Y/N | |
| End User Lead | | | +/=/− | Y/N | |
| Technical Eval | | | +/=/− | Y/N | |
| Procurement | | | +/=/− | Y/N | |
Step 3 — Design the Multi-Thread Account Strategy
Never rely on one relationship in an enterprise deal. Build multiple:
Multi-Threading Rules:
- Aim for 3+ engaged stakeholders before progressing to proposal stage
- Executive-to-executive connection neutralizes junior-level blockers
- If your champion leaves, you need another thread or the deal is dead
- Connect directly with the Economic Buyer at least once before proposal
How to Open New Threads:
Ask your champion: "As we get further in this process, who else is typically involved in decisions like this? I'd like to make sure their questions are answered early."
Direct outreach to Economic Buyer (once champion is warm):
"Hi [Name], I've been working with [Champion Name] on a potential partnership and they thought it would be valuable for us to connect briefly. I'd love 15 minutes to share the business case from my side — [Champion] speaks highly of how you think about [relevant strategic priority]."
Step 4 — Build the Enterprise Sales Process
Enterprise deals require a structured, predictable process from first contact to close:
Stage-by-Stage Enterprise Playbook:
Stage 1 — Account Entry (Weeks 1–4)
- Identify 3+ potential contacts in account
- Research trigger events, strategic priorities, pain signals
- Secure first meeting through warm intro, cold outreach, or event
- Meeting goal: Get champion to describe the problem in their words
Stage 2 — Discovery & Qualification (Weeks 4–8)
- Run structured discovery across 3+ stakeholders
- Map the buying committee (Step 2 above)
- Confirm budget range is realistic for your solution
- Identify compelling event (why now vs. never?)
- Deliverable: Internal champion brief + verbal green light to proceed
Stage 3 — Solution & Evaluation (Weeks 8–16)
- Deliver a tailored business case (quantified ROI, not features)
- Complete technical evaluation (security review, integration assessment)
- Run a pilot or POC if required — with success criteria agreed upfront
- Engage Economic Buyer at least once in this phase
Stage 4 — Proposal & Commercial (Weeks 12–20)
- Present proposal in a live meeting — never send without a walkthrough
- Build mutual close plan with named owners and dates
- Navigate procurement with transparency (give them your standard docs early)
- Finalize legal with redline strategy ready
Stage 5 — Close (Variable)
- Champion confirms verbal commitment
- Economic Buyer signs off on business case
- Procurement / Legal finalizes terms
- Contract execution
Step 5 — Build the Enterprise Business Case
The Economic Buyer doesn't care about features — they care about ROI. Build it for them:
Business Case Formula:
CURRENT STATE COST:
[Quantify the cost of the problem they're experiencing]
Example: 50 hours/week wasted × $80/hour × 52 weeks = $208,000/year in lost productivity
RISK OF DOING NOTHING:
[What happens in 12 months if they don't solve this?]
Example: "At current growth rate, this problem scales to $500K+ in year 2"
INVESTMENT:
[Your pricing, clearly stated]
EXPECTED RETURN:
[Quantified outcome — conservative estimate]
Example: 40% reduction in wasted time = $83,200/year recovered
PAYBACK PERIOD:
[Time to break even]
Example: "You'll recoup the full investment within [X months]"
3-YEAR ROI:
[Total value delivered over 3 years vs. total cost]
Example: "$830,000 in recovered value vs. $[price] invested = [X]x ROI"
Step 6 — Enterprise Deal Velocity Accelerators
Tactics that specifically speed up slow enterprise deals:
- Exec-to-exec meeting: Have your CEO/CRO meet their executive sponsor — deals move faster at peer-to-peer levels
- Reference call: Connect them with a current customer who had the same concern — one peer testimonial outperforms all your materials
- Pilot with success criteria: Agree upfront what success looks like in a pilot — a passed pilot becomes the de facto purchase justification
- Mutual close plan: Put all remaining steps, owners, and dates in writing — deals without a written plan are 2x more likely to slip
- Compelling event tie-in: Connect the deal to their strategic calendar (budget cycle, board review, product launch)
Output Format
Deliver:
- Enterprise Account Score (for target account)
- Buying Committee Map (all 6 roles with names/status)
- Multi-Threading Strategy (how to build 3+ relationships)
- Stage-by-Stage Enterprise Sales Plan
- Quantified Business Case (ready for Economic Buyer)
- Top 3 Deal Velocity Accelerators for this specific deal
Pro Tips
- In enterprise sales, speed is your enemy — slow is smooth, smooth is fast. Rushing creates mistakes that blow up deals.
- The champion is only as powerful as their political capital internally. Assess their influence before betting the deal on them.
- Never present a proposal that surprises anyone — the best proposal meetings are reviews, not reveals
- Enterprise deals die in the handoff between champion and economic buyer more than anywhere else — own that transition
- If you've been in "evaluation" for more than 3 months with no defined next step, you don't have a deal — you have a conversation