Deal Desk

Deal Desk

Overview

Deal structuring is where strategy meets money. The difference between a deal that closes at list price and one that gets discounted 40% is usually not the product — it's how value was communicated and the business case was constructed.

This skill covers pricing model selection (Ramanujam), business case building (ValueSelling Framework), discount authority frameworks, and negotiation strategy grounded in Command of the Message value articulation.

When to Use

• "Structure this deal"
• "Build a business case for [prospect]"
• "What pricing model should we propose?"
• "How much discount should we offer?"
• "Prepare for a pricing negotiation"
• "Create a proposal for [company]"

Authoritative Foundations

Madhavan Ramanujam's Monetizing Innovation: pricing should be designed around customer willingness-to-pay, not cost-plus or competitor-minus. The 2x2 model (price sensitivity × differentiation) determines which pricing model fits.

ValueSelling Framework: every deal conversation should ladder up to quantifiable business impact. "What's this worth to you?" is the question that determines pricing power.

Force Management Command of the Message: premium pricing is defendable when value differentiation is clear and provable.

Step-by-Step Process

Phase 1: Intake

Ask the user:

1. Deal size and deal stage
2. Prospect's budget range (if known)
3. Competitors in the deal and their pricing
4. Champion strength and economic buyer access
5. Timeline and urgency

Phase 2: Pricing Model Selection

Phase 3: Business Case Construction

Template: templates/business-case.md — current state cost, future value, investment, ROI, risk of inaction. Deep ROI → roi-calculator.

Phase 4: Discount Authority

Never discount without getting something in return: multi-year commit, case study permission, reference call, logo rights, or expansion commitment.

Document every request in templates/discount-authority.md. Land-and-expand deals: crm-toolkit land-expand-account-plan — protect expansion ACV.

Phase 5: Enterprise Security & Customer Data (GTM)

Enterprise deals often stall on security review and data exchange — not price. This is GTM coordination, not infra engineering.

When security review enters the deal:

Full timing playbook → references/security-questionnaire-deal-guide.md ( repo root ). SOC 2 / pen test implementation → soc2-compliance, security-assessments.

Legal GTM (commercial velocity): Eunice Buhler (G2 GC) — legal as deal accelerator via availability, published SLAs, and "get to yes" commercial mindset. Ironclad CLM — situational approval swimlanes, legal-pre-approved MSA variants, CRM-native order forms. Canonical → references/legal-gtm-playbook.md (Pattern 29). DPA timing aligned with references/gtm-data-exchange-playbook.md — enterprise DPA during negotiation, before production data intake.

Customer data exchange (what reps request from buyers):

• Minimum data for the next milestone — not "send everything"
• Approved channels only: customer-owned upload, secure file share, in-app import — never email attachments or Slack files with PII
• Go/no-go before production data: contract scope, DPA status, retention date

Canonical SOP → references/gtm-data-exchange-playbook.md. Checklist → templates/customer-data-exchange-checklist.md.

Red flags that kill deals: full CRM export in discovery; AE solo-filling security questionnaires; POC on production when sandbox exists; no handoff of what data was already exchanged.

Output Format

Deal structure document with pricing recommendation, business case, discount framework, and negotiation strategy.

Quality Check

• Pricing model matched to customer's usage pattern and value drivers
• Business case includes both current-state cost and future-state value
• ROI figures are conservative and sourceable
• Discount authority rules documented and enforced
• Every discount tied to a concession from the prospect

Common Pitfalls

1. Discounting without exchange. A 20% discount with nothing in return is just leaving money on the table. Always trade.

2. Vague business case. "You'll save money" isn't a business case. "Your team spends 40 hours/week on [task] at $X/hour = $Y/year. Our solution reduces that to 10 hours. Annual savings: $Z. Payback: 4 months."

3. Premature pricing discussion. Discussing price before establishing value makes every number sound expensive. Value first, price second.

4. One price for everyone. Different segments, different willingness- to-pay. A 10-person startup and a 500-person enterprise shouldn't see the same pricing.

Execution Artifacts

• references/framework-notes.md
• templates/output-template.md
• scripts/check-output.py
• templates/business-case.md — ROI business case structure
• templates/discount-authority.md — Approval + trade documentation
• templates/customer-data-exchange-checklist.md — Pre/on/post-sale data exchange gates
• references/legal-gtm-playbook.md — Eunice Buhler + Ironclad commercial counsel for sales (Pattern 29)
• references/gtm-data-exchange-playbook.md — Canonical customer data exchange SOP (repo root)
• references/security-questionnaire-deal-guide.md — When security review enters the deal (repo root)

Related Skills

• pricing-strategy: Overall pricing model design
• roi-calculator: Detailed ROI calculation and business case tools
• pipeline-management: Track deals through negotiation and close
• customer-onboarding: Post-sale data handoff and implementation boundaries
• soc2-compliance, security-assessments: Building trust artifacts (founder-led)
• revenue-team-onboarding: Rep security hygiene before customer contact