Sales comes to you: "We have a $500K deal but the customer needs custom packaging. Can we bundle Products A, B, and C with a 20% discount?"
You check with product. Finance wants to approve pricing. Legal needs to review. The deal stalls for 3 weeks while everyone scrambles to figure out if this is a good idea.
Meanwhile, the prospect moves on to a competitor who could respond in 48 hours.
This is the reality of enterprise sales: customers don't fit into your standard tiers. They want custom packaging, negotiated pricing, and unique terms.
Most product marketing teams either say "stick to standard pricing" (and lose deals) or say yes to everything (and create pricing chaos).
The solution: a structured deal desk process that lets you move fast on strategic deals while maintaining pricing integrity.
After supporting deal desk at three companies (two with clean processes, one disaster), here's the framework that works.
What Is Deal Desk (And Why PMM Should Care)
Here's what actually happens: Deal desk is the function that approves custom deals outside your standard pricing and packaging. It's the relief valve that lets enterprise sales move fast without blowing up your entire pricing strategy.
The requests come in all shapes. Sometimes sales wants to bundle features from different tiers. Other times they need discounts beyond their approval authority. You'll see custom terms—annual contracts with monthly billing, performance guarantees that make legal nervous. And there's always the multi-year deals with ramp commitments where a customer promises to grow from 100 to 500 users, but only if you give them a sweetheart deal today.
This lands squarely on PMM's desk because packaging is product positioning, which is fundamentally your job. Every custom package you approve sets precedent for future pricing. Sales needs battle cards and pitch support for these one-off deals. And somebody has to prevent pricing erosion while maintaining the integrity of your tier structure—that somebody is you.
The cast of characters on every deal desk request looks like this:
- PMM: Packaging logic, competitive positioning
- Finance: Discount approval, revenue recognition
- Legal: Contract terms, liability
- Sales ops: Deal structure, CRM tracking
- Product: Feature feasibility, roadmap commitments
The Deal Desk Framework
Tier 1: Standard Deals (Sales Self-Serve)
What it is: Deals that fit within published pricing and packaging
Examples:
- Customer buys Pro tier at list price
- Standard discount (10-15% for annual prepay)
- No custom terms
Approval: None needed (sales closes independently)
PMM role: None (already documented in pricing/packaging)
Tier 2: Minor Custom Deals (Sales Manager Approval)
What it is: Small deviations from standard pricing
Examples:
- 15-20% discount (beyond sales rep authority)
- Monthly payments on annual contract
- Add-on features from next tier up
Approval: Sales manager (same-day turnaround)
PMM role: Define what's allowed in "minor custom" category
Max deal size: <$50K ARR
Tier 3: Major Custom Deals (Deal Desk Review)
What it is: Significant packaging or pricing changes
Examples:
- Custom bundle (features from multiple tiers)
- 20-30% discount
- Multi-year deal with ramp (Year 1: 100 users, Year 2: 500 users)
- Custom SLAs or performance guarantees
Approval: Deal desk review (48-72 hour turnaround)
PMM role: Review packaging logic, approve messaging, create custom materials if needed
Deal size: $50K-$250K ARR
Tier 4: Strategic Deals (Executive Approval)
What it is: Transformational deals with unique terms
Examples:
- $500K+ ARR
- Custom product development
- Equity or revenue share arrangements
- Lighthouse customer (willing to take reference risk)
Approval: CFO, CRO, or CEO sign-off
PMM role: Full GTM support (custom deck, case study planning, launch coordination)
Deal size: $250K+ ARR
The Deal Desk Request Process
Step 1: Sales Submits Request
Required info:
- Customer name and details
- Deal size (ARR, contract length)
- What they're requesting (packaging, pricing, terms)
- Why standard pricing doesn't work
- Competitive situation
- Close timeline
Format: Standardized form (Airtable, Salesforce, or Google Form)
Submission triggers: Automated notification to deal desk team
Step 2: PMM Reviews Packaging (Within 24 Hours)
PMM asks:
- Does this packaging make sense? (Or is sales just giving away features)
- Does it set bad precedent? (Will every future customer ask for this?)
- Can we deliver on it? (Check with product on feasibility)
- How do we position it? (What's the narrative?)
PMM decision:
- Approve: Packaging makes sense, proceed to finance
- Modify: Counter with alternative packaging
- Deny: Packaging doesn't make sense, explain why
Step 3: Finance Reviews Pricing (Within 24 Hours)
Finance asks:
- Does pricing meet margin requirements?
- Is discount justifiable given deal size and strategic value?
- Does payment structure work for cash flow?
- What's the revenue recognition impact?
Finance decision:
- Approve: Pricing works
- Modify: Counter with adjusted pricing
- Deny: Pricing doesn't meet business requirements
Step 4: Legal Reviews Terms (If Needed)
Legal asks:
- Are custom SLAs feasible?
- Do we accept liability for performance guarantees?
- Are custom data handling/security terms acceptable?
Timeline: 48-72 hours (longer for complex terms)
Step 5: Deal Desk Decision (Within 72 Hours Total)
Possible outcomes:
- Approved as requested
- Approved with modifications (sales takes back to customer)
- Denied (with explanation and alternative offered)
Output:
- Approved deal structure document
- Custom quote
- Any custom sales materials needed
The PMM Deal Desk Playbook
When to Say Yes
Good reasons to approve custom packaging:
1. Strategic customer (lighthouse account)
- Well-known brand that will be great reference
- Willing to do case study, speak at events
- Acceptable to give preferential pricing for advocacy
2. Market expansion
- First customer in new vertical or geography
- Willing to discount to prove use case
- Learning opportunity that informs future packaging
3. Competitive displacement
- Pulling customer from major competitor
- Strategic win worth pricing concession
- Sends market signal
4. Large deal with clear ROI
- $500K+ ARR
- Pricing still meets margin requirements
- Sets precedent for future enterprise deals
5. Product validation
- Customer willing to beta test new features
- Feedback will improve product roadmap
- Discount in exchange for early adoption risk
When to Say No
Bad reasons that sales will request:
1. "Customer says they can't afford list price"
- Translation: Sales hasn't sold value effectively
- Response: "Help them understand ROI, don't discount"
2. "Competitor is 20% cheaper"
- Translation: We're not differentiated enough
- Response: "Sell on value, not price. What do we offer that they don't?"
3. "We're behind quota and need this deal"
- Translation: Bad sales execution shouldn't drive bad pricing
- Response: "Hitting quota with bad deals creates long-term problems"
4. "Every other customer has this custom package"
- Translation: Sales is creating precedent that undermines standard pricing
- Response: "Show me 3 examples. If true, we need to fix standard packaging."
5. "Customer wants features from Enterprise tier at Pro price"
- Translation: They want to pay less for more
- Response: "That's what upgrades are for"
The Counter-Offer Strategy
Don't just say yes or no. Offer alternatives.
Example 1:
Request: "Customer wants Enterprise features at Pro pricing ($10K/year)"
Counter: "Approve Pro tier ($10K) with one Enterprise feature as add-on ($3K). Total: $13K. Still 35% discount from Enterprise list price ($20K), but maintains tier integrity."
Example 2:
Request: "Customer wants 50% discount on $100K deal"
Counter: "Approve 30% discount ($70K) if they:
- Commit to 3-year contract
- Provide case study
- Speak at our user conference Discount justified by advocacy value."
Example 3:
Request: "Customer needs monthly billing but wants annual contract pricing"
Counter: "Approve annual pricing ($100K) with quarterly billing (4 payments of $25K). Meets their cash flow needs, reduces our payment risk vs. monthly."
The Custom Deal Documentation
For every approved custom deal, document:
1. Deal Summary (1-Page)
Customer: [Name], [Industry], [Size]
Deal structure:
- ARR: $150K
- Contract length: 2 years
- Packaging: Custom bundle (Pro + 3 Enterprise features)
- Pricing: 25% discount from list
Justification:
- Strategic customer in new vertical (healthcare)
- Willing to provide case study and reference
- Sets precedent for future healthcare deals
Approved by: PMM, Finance, Legal Date: [Date]
2. Sales Talking Points
How sales should position this package:
"We created a custom package for your healthcare compliance needs:
- Core Pro features for launch management
- Added Enterprise-level security (HIPAA compliance)
- Advanced analytics for audit trails
- Custom SSO integration
This is a strategic package we're offering to lighthouse healthcare customers."
3. Renewal/Expansion Strategy
Notes for future renewals:
- Custom pricing was 25% discount as early healthcare customer
- At renewal, recommend moving to standard Enterprise tier (more features, less custom)
- Expansion opportunities: Add 50 more seats, upgrade to full Enterprise
How to Prevent Deal Desk Chaos
Problem: Every deal becomes custom. Sales stops selling standard pricing.
Solution: Policies and Guardrails
Policy 1: Discount Caps
By deal size:
- <$25K: Max 10% discount (sales manager approval)
- $25K-$100K: Max 20% discount (deal desk approval)
- $100K-$500K: Max 30% discount (VP approval)
- $500K+: Custom (executive approval)
Exceptions: Must have strategic justification (lighthouse customer, competitive win, multi-year commit)
Policy 2: Custom Package Limits
Allowed:
- Adding 1-2 features from higher tier
- Bundling related products
- Volume-based pricing (500+ seats)
Not allowed:
- Cherry-picking features from every tier
- Creating one-off SKUs
- Removing core features from standard tier
Policy 3: Standard-to-Custom Ratio
Goal: 70%+ of deals close at standard pricing
Track monthly:
- % of deals requiring deal desk approval
- Average discount by tier
- Most common custom requests
If custom >30%: Standard packaging is broken. Fix it, don't keep customizing.
Policy 4: Sunset Custom Packages
For custom packages:
- Revisit at renewal
- Offer migration to standard pricing
- Don't let custom packages proliferate indefinitely
Goal: Consolidate custom deals into standard tiers over time
Measuring Deal Desk Success
Metrics to track:
Efficiency Metrics
- Turnaround time: Median hours from request to decision (target: <72 hours)
- Approval rate: % of requests approved (target: 60-70%)
- Sales satisfaction: Survey sales on process (target: 7+/10)
Business Metrics
- Win rate: Custom deals vs. standard deals (custom should be higher)
- Deal size: Average ARR of custom deals (should be 2-3x standard)
- Margin: Average margin on custom deals (should still meet company targets)
Health Metrics
- Standard deal %: Target 70%+ of deals at standard pricing
- Discount creep: Average discount over time (should be stable or decreasing)
- Package proliferation: # of unique custom packages (should be managed, not growing indefinitely)
The Uncomfortable Truth
Deal desk is where idealistic pricing meets real-world sales. Your beautiful tiered pricing looks great on the website, fits perfectly on your pricing page, makes total sense to the board. Then a customer walks in and says they need Enterprise features but can only pay Pro prices. Or your competitor is offering the same thing for 30% less. Or—my personal favorite—they'll give you a reference if you give them 40% off.
You're stuck between two bad options. Hold the line on pricing and maintain integrity, but lose strategic deals to competitors who are more flexible. Or say yes to everything, hit quota in the short term, but create unsustainable pricing and an operational nightmare as custom deals proliferate.
The answer is structured flexibility. Here's what actually works: Be flexible on strategic deals with clear justification—lighthouse customers, competitive displacements, market expansion opportunities. Be rigid on protecting pricing integrity for 70% or more of your deals.
The best deal desk processes I've seen share six characteristics. They respond fast, usually within 48-72 hours because enterprise deals move quickly. They have clear approval criteria so sales knows what's even worth requesting. They counter with alternatives instead of just saying yes or no—this is the art of the deal desk. They document every precedent because what you approve today becomes tomorrow's baseline. They measure discount trends and package proliferation to catch pricing erosion early. And they revisit custom packages at renewal to bring customers back to standard pricing over time.
Done right, deal desk lets you move fast on strategic deals without destroying your pricing model. You can close the $500K enterprise deal with custom terms in 72 hours instead of 3 weeks. You can maintain pricing integrity across 70% of deals while still having flexibility for the strategic 30%. You can prevent sales from creating 50 one-off SKUs that become an operational nightmare.
Get it wrong, and here's what happens: You'll have 50 custom SKUs that nobody can track. You'll have no pricing power because every customer expects a discount. You'll have a sales team that can't sell without discounting 30% because that's become the baseline. And you'll have a product marketing function that spends all its time approving custom deals instead of building strategy.
Build the process. Document the policies. Measure the metrics. Stick to it. Your pricing model depends on it.