UitbreidenOS Deal Desk Skill
When to activate
- Structuring a complex enterprise deal (multi-year, custom terms, bundles)
- Reviewing a customer-proposed contract for commercial red flags
- Setting discount approval thresholds and escalation policies
- Analysing deal economics (margin, payback, LTV) before approving
- Creating or updating commercial policy (pricing guardrails, bundling rules)
When NOT to use
- Legal contract review for compliance risk — use the vendor-contract-review or diligence-review skill
- Pricing strategy and tier design — use the pricing-strategy skill
- Revenue forecasting — use the revenue-operations skill
- Customer success and renewal playbooks — use the customer-success skill
Instructions
Deal structuring
Structure a deal for [customer].
Customer: [name, company size, industry]
Deal type: [new logo / expansion / renewal / multi-year]
ARR requested: $[X]
Products / tiers requested: [list]
Contract length: [12 / 24 / 36 months]
Requested start date: [date]
Special requirements: [custom SLA / dedicated support / custom integration / data residency]
Deal structure review:
1. PRICING INTEGRITY:
What is the list price for this configuration?
Customer is asking for: $[X] ([X]% off list)
Is this within standard discount authority? [rep / manager / VP / CRO level]
What is the justification? [volume / strategic / competitive / renewal retention]
2. DEAL ECONOMICS:
ACV: $[X]
Estimated CAC for this deal: $[X] (sales cycle + SE + legal time)
Gross margin at this price: [X]%
CAC payback at this price: [X] months
Is this economically viable? [yes / borderline / no — escalate]
3. TERM STRUCTURE:
Payment terms: [net 30 / annual upfront / quarterly]
Multi-year lock-in: [year 2 and 3 pricing committed at list / CPI + X%]
Renewal auto-renew: [yes / 90-day notice]
Early termination clause: [yes — risk / no — standard]
4. NON-STANDARD TERMS TO FLAG:
🔴 Uncapped liability — reject or escalate to legal
🔴 Unlimited indemnification scope — escalate
🔴 SLA penalties as sole remedy — accept if penalties are capped
🟡 Most-favoured-nation pricing clause — flag; may constrain future pricing
🟡 Data portability requirements at termination — flag; confirm engineering can fulfil
🟡 Sub-processor restrictions — flag; confirm current sub-processor list is acceptable
5. DEAL APPROVAL:
Approver at this discount level: [name/role]
Required documents before approval: [SOW / security questionnaire / legal review]
Expected close date: [date]
Output: deal approval recommendation with specific conditions.
HUMAN APPROVAL REQUIRED for all discounts > standard rep authority.
Discount approval policy
Design a discount approval policy for [company].
Sales team size: [X reps]
Deal sizes: [$X typical ACV, $X max ACV]
Current discount problem: [too much / inconsistent / no policy / margin compression]
Standard discount authority matrix:
| Discount level | Approved by | Max ACV | Conditions |
|---|---|---|---|
| 0-10% off list | AE (no approval needed) | Any | Standard terms only |
| 11-20% off list | Sales Manager | Any | Written justification required |
| 21-30% off list | VP Sales | Any | Deal review meeting required |
| 31-40% off list | CRO | > $100K ACV only | CEO awareness + deal economics review |
| > 40% off list | CEO + Board | Strategic deals only | Full deal desk review |
Discount justification categories:
- Volume: > X seats / > X usage volume
- Strategic: reference customer / case study / partnership value
- Competitive: documented competitive displacement
- Retention: at-risk renewal, competitor evaluation in progress
- Speed: sign by [date] for current-quarter close
Discount guardrails (non-negotiable):
- No discount below minimum gross margin floor ([X]% — set by finance)
- Multi-year deals: year 2+ pricing must be at list or CPI-adjusted — never locked at discounted rate
- No retroactive discounts on already-closed deals
- Discount applies to ARR only — professional services at list always
Generate the approval policy for my company and sales team structure.
HUMAN APPROVAL REQUIRED for every deal above rep authority level.
Contract terms review
Review these contract terms for commercial risks.
Contract type: [MSA / Order Form / SaaS subscription agreement]
Our role: [vendor / customer]
Contract value: $[X] / [term]
Commercial red flags to check (flag as RED/YELLOW/GREEN):
LIABILITY:
🔴 Uncapped liability — must negotiate a cap (standard: 12 months of fees)
🔴 Liability cap < 3 months of fees — too low; negotiate to 12 months minimum
🟡 No carve-out for gross negligence or willful misconduct — verify cap applies
PRICING AND PAYMENT:
🔴 Right to audit with unlimited scope — limit to relevant records, reasonable notice
🟡 Price increase cap not specified — add CPI or [X]% annual cap
🟡 Auto-renew notice period > 90 days — customer may request longer notice
🟢 Net 30 payment terms — standard
INTELLECTUAL PROPERTY:
🔴 Broad work-for-hire clause claiming all IP — limit to specific deliverables only
🔴 IP created during support or implementation claimed by customer — exclude
🟡 License scope is "worldwide, perpetual, irrevocable" — standard for SaaS
TERMINATION:
🔴 No termination for convenience — must have 30-90 day notice right
🟡 Termination triggers are overly broad ("any breach") — should require cure period
🟡 Effect of termination: customer data deletion timeline not specified — add 30-day grace
DATA:
🔴 No DPA attached (if processing personal data) — require DPA
🔴 Data ownership ambiguous — we own customer data; customer owns their content
🟡 Audit rights for data security — limit to third-party audit reports (SOC 2); not direct access
Produce: redline recommendations for each RED/YELLOW item.
LEGAL REVIEW REQUIRED before signing any agreement.
Deal economics analysis
Analyse the economics of [deal].
ACV: $[X]
Term: [X months]
TCV (total contract value): $[X]
Gross margin at this price: [X]%
CAC invested: $[X] (sales salary + commission + SE time + legal)
Implementation cost (if any): $[X]
Deal economics:
CAC payback period:
= CAC / (ACV × gross margin %)
= $[X] / ($[X] × [X]%)
= [X] months
At gross margin [X]%, this deal pays back its acquisition cost in [X] months.
Benchmark: < 12 months = excellent; 12-18 months = acceptable; > 24 months = marginal
LTV calculation (assuming [X]% annual churn):
Average customer lifetime = 1 / churn rate = [X] years
LTV = ACV × gross margin % × lifetime
= $[X] × [X]% × [X] years = $[X]
LTV:CAC ratio = $[X] / $[X] = [X]x
Benchmark: > 3x = healthy; > 5x = excellent; < 2x = concern
Revenue recognition:
- Annual upfront: full TCV recognised over the term (ASC 606 ratable)
- Monthly: recognised monthly as delivered
Multi-year implications:
- Locking customer at [discounted] rate for 3 years: revenue predictability
- Risk: pricing power lost; if list price increases 20%, this customer stays at the old rate
Decision: [approve / approve with conditions / escalate]
Conditions: [if any — e.g. "approve at this price if term is 24 months upfront"]
HUMAN SIGN-OFF REQUIRED before deal closure.
Example
User: A Fortune 500 customer wants our $85K/year enterprise plan for $55K/year (35% off list), 3-year deal, with a data export right on termination, net 90 payment terms, and an MFN clause. Deal or no deal?
Claude's analysis:
Discount (35% off list): Requires CRO-level approval under standard policy. Justification needed: strategic logo, competitive pressure, or volume commitment. At $55K × 3 = $165K TCV — worth the escalation if the customer is a genuine reference.
Term-by-term:
Net 90 payment terms → 🔴 Push back. Net 30 is standard. Net 60 maximum for enterprise. Net 90 = 3-month working capital impact at this deal size. Counter: offer 2% early payment discount at net 10, or hold at net 30 with no discount.
Data export right on termination → 🟢 Standard and reasonable. Confirm your engineering team can deliver a machine-readable export within 30 days — this is common and worth committing to.
MFN clause → 🔴 Reject or strictly scope it. An unlimited MFN ("we get your best price to any customer") means if you ever sell a similar deal at a lower price, this customer automatically gets that lower price too. Counter: "MFN applies only to deals of equal or greater ACV, same term, signed within 12 months."
Overall recommendation: Approve with two conditions: (1) payment terms negotiated to net 30 or 60 (not 90), and (2) MFN scoped to comparable deals only. CRO sign-off required before sending final terms.
HUMAN APPROVAL REQUIRED. Do not send revised terms without CRO signature on the deal summary.