executing-plans
executing-plans
Use when executing an implementation plan in the current session as the implementer yourself — your human partner chose inline execution, or no subagent tool is available
expansion-discoveryIdentify expansion signals and structure upsell or cross-sell conversations using land-and-expand and Net Revenue Retention principles. Use when user says "upsell", "expansion", "cross-sell", "grow the account", "increase ARR", "find expansion opportunities", "NRR improvement", "upgrade conversation", "add-on", "renewal and expand", or "land and expand" - e…
Independent GitHub snapshot · Automated classification · Original documentation governs
Based on "Farm Don't Hunt" by Guy Nirpaz and "The Customer Success Economy" by Mehta & Steinman, expansion is not a sales motion - it is a CS motion. Customers expand when they have achieved value in the current footprint and have a clear problem that an expanded product solves. Pushing expansion before value is established destroys trust. Waiting too long leaves revenue on the table.
The core insight: Net Revenue Retention (NRR) is the most important SaaS metric. An NRR above 110% means expansion is compounding growth - even with some churn, you're growing. A CSM who surfaces and advances expansion opportunities is directly contributing to company revenue.
Expansion should only be pursued when the current footprint is healthy. Check all three:
If any of these are false, fix the current footprint first. An expansion push on a shaky foundation accelerates churn, it doesn't prevent it.
Usage signals (pull from your product analytics):
Relationship signals (look for these in call notes and emails):
Conversation signals (direct indicators of expansion readiness):
Document which signals are present for [customer name].
| Signal | Expansion Type | Conversation Approach |
|---|---|---|
| Approaching seat limit | Volume expansion | Proactive - bring data, frame as planning ahead |
| Using competitor for adjacent use case | Cross-sell / consolidation | Problem-led - quantify the cost of fragmentation |
| New team or department interested | New use case expansion | Reference-led - show how current team's results can replicate |
| Power users hitting tier limits | Tier upgrade | Value-led - show the ROI gap between tiers |
| New strategic initiative | New use case | Executive-led - align to the initiative, not the feature |
Do not bring a pricing sheet to an expansion conversation. Bring value data and a problem framing.
Structure for the expansion conversation:
Recap current value: "Since you started with us, [specific outcome with data]. Your team is doing [specific usage behavior]."
Bridge to the observed signal: "I noticed [specific signal]. I wanted to ask you about it directly."
Explore the problem (use open questions):
Connect to your solution (only after the problem is articulated): "Based on what you've described, [specific feature or tier] is designed exactly for this. Customers in similar situations used it to [specific outcome]."
Next step, not a close: "I'd like to put together a proposal that shows the ROI. Can we get 30 minutes with [economic buyer] to walk through it?"
Never close expansion in the discovery call. The goal of this conversation is to earn a proposal meeting, not to get a verbal commit.
Before advancing the opportunity, align internally with sales (if separate) and your manager.
[Customer name] - Expansion Brief
Account ARR: [current ARR] Potential expansion ARR: [estimated value] Expansion type: Volume / Tier upgrade / Cross-sell / New department Signal(s) identified: [list] Customer contact: [champion name and title - no personal last names in template] Economic buyer: [who controls budget] Discovery call date: [date] Problem confirmed by customer: [1-2 sentence summary in customer's words] Proposed solution: [specific product tier, add-on, or seat increase] Comparable customer reference: [similar customer who expanded and got X outcome] Next step: [specific meeting or proposal with date]
Expansion conversations stall when the customer cannot justify the incremental cost internally. Build the ROI case before the proposal meeting.
Framework:
Example: "Your current investment is $X/year. Adding [module] is $Y/year incremental. Based on how similar customers have used it, you would expect [outcome] within [timeframe], which pays back the incremental cost in [N] months."
1. Expansion before value established Bad: Pitching an upsell at month 2 of onboarding before the customer has hit their first milestone. Good: Wait for a measurable outcome. Expansion is earned, not scheduled.
2. Price-led conversations Bad: "We have a special pricing offer on our enterprise tier this quarter." Good: "You mentioned you're handling [problem] with a separate tool. I want to show you what it would look like to consolidate."
3. Surprise the customer with a proposal Bad: Sending a contract expansion proposal without a prior discovery conversation. Good: Discovery call first, always. The proposal follows confirmed problem understanding.
4. Expanding the wrong contact Bad: Running the expansion conversation with the champion but skipping the economic buyer. Good: Map the economic buyer early. The champion needs to be able to get budget approval. If they can't, get to the person who can before investing in the proposal.
5. Treating expansion as a sales handoff Bad: "This is a growth opportunity, I'll loop in sales." Good: CSM drives expansion discovery. Sales may assist on negotiation and legal. The relationship and the value case belong to CS.