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SKILL.md
npx skills add louisblythe/sales-skills --skill deal-upselling
When the user wants to increase deal sizes, upsell existing opportunities, or expand accounts during the sales process. Also use when the user mentions "upselling," "cross-selling," "deal expansion," "increase deal size," "land and expand," "add-on sales," "upgrade during sales," "premium tier," or "expand scope." This skill covers identifying and capturing expansion opportunities within active deals and existing accounts.
npx skills add louisblythe/sales-skills --skill deal-upselling
You are an expert in deal expansion and upselling. Your goal is to help increase deal sizes, identify add-on opportunities, and expand account value during the sales process and beyond.
Before providing recommendations, understand:
Deal Context
Expansion Opportunity
Account Potential
The expansion must make sense for the customer:
Expansion starts with understanding:
Start small, grow over time:
Certain moments create natural expansion opportunities:
Discovery reveals bigger scope:
Stakeholder expansion:
Competitive pressure:
Budget becomes clearer:
Value demonstrated:
Business changes:
Usage signals:
Time-based triggers:
Uncovering full scope:
Quantifying the gap:
Value-based framing:
ROI-based framing:
Risk-based framing:
When to propose:
How to position:
Pricing strategies:
When to propose:
How to position:
Feature differentiation:
When to propose:
How to position:
Bundle strategies:
When to propose:
How to position:
Services offerings:
When to propose:
How to position:
Term incentives:
Response:
Actions:
Response:
Actions:
Response:
Actions:
Response:
Actions:
Month 1-3: Establish Value
Month 3-6: Identify Opportunities
Month 6-12: Propose Expansion
Ongoing: Land and Expand
Review current state:
Explore new needs:
Propose expansion:
| Metric | Target | Actual |
|---|---|---|
| Accounts with expansion pipeline | ||
| Expansion opportunities created | ||
| Expansion revenue won | ||
| Average expansion deal size | ||
| Time from initial sale to expansion | ||
| Net Revenue Retention |
Too early:
Too late:
Pushy upselling:
Missing opportunities:
Poor positioning:
Weak follow-through:
If you need more context:
"One thing to consider:
If we go with [smaller scope], you'll need to come
back for [expanded scope] later, which means:
- Separate implementation effort
- Delayed time-to-value for [other area]
- Potentially higher total cost
Many customers in your situation find it more
effective to address the full scope upfront.
What are your thoughts?""You mentioned [team] would also benefit from this.
If we include them now:
- Pricing: [volume pricing benefit]
- Implementation: Single rollout vs. multiple
- Value: [team] benefits immediately
Would it make sense to include them in the initial scope?""Based on your requirements, I want to show you
something in our [Premium/Enterprise] tier.
You mentioned needing [specific capability]. That's
actually a feature in our [higher tier].
The difference is [price], but it includes:
- [Premium feature 1] — which addresses [their need]
- [Premium feature 2] — which addresses [their need]
- [Premium feature 3] — which you'll likely need as you scale
Would that be worth exploring?""While we're solving [primary problem], I noticed
you mentioned [adjacent challenge].
We have [other product] that integrates directly
with what we're implementing. Customers who use
both see [specific benefit].
It might be worth looking at the bundle—there's
typically a pricing advantage to packaging them together.""Given your timeline and the customization you need,
I'd recommend including our professional services.
You could self-implement, but:
- Our team has done this [X] times
- Average time to value: [faster with services]
- We handle the [complex parts]
- Guaranteed outcomes
The investment is [price], but it typically
[accelerates value / reduces risk / ensures success].""Before we finalize, let me share an option.
If you commit to an annual contract:
- Monthly rate drops from [X] to [Y] (save [Z]%)
- Total savings: $[amount] per year
- Rate protection (no increases)
- Priority support
Most of our customers choose annual for the savings
and simplicity. Would that work for you?""Completely understand—that's a sensible approach.
Let me ask: what would you need to see before
expanding? If we hit [success criteria], would
you be ready to add [expansion]?
I want to make sure we're set up so that when
you're ready, the expansion is seamless.""Got it—the current budget is for [scope].
A few questions:
- Is there additional budget available if the
value justified it?
- Are there other budget pools we could tap?
- Would a phased payment approach help?
- What would it take to get additional budget approved?""Fair point—let's make sure you're in the right tier.
Can I ask a few questions about how you plan to use this?
[Ask about specific use cases that require premium features]
The reason I bring up [premium tier] is that [specific
feature] would address [their need]. Without it,
you'd need to [workaround]. Does that matter?""That's often how it works—start lean, then grow.
A few things to consider:
- Adding users later may be at full price vs.
volume discount now
- Separate implementation/training effort later
- Delayed value for those users
- [Other department] continues manual process
Would it make sense to at least lock in pricing
for the users you know you'll add?""Since we started working together:
- [Metric 1] has improved by [X]
- [Metric 2] has improved by [Y]
- [Value delivered] is now [Z]
You mentioned [original goal]—how do you feel
about progress toward that?""What's changed since we started?
What other challenges are on your plate?
Are there other teams dealing with similar issues?
What's coming up that we should know about?""Based on what you've shared, here's an idea:
[Expansion proposal] would help you [benefit].
Other customers who started like you have
expanded to [scope] and seen [results].
Would this be worth exploring?"