Premium GTM Situation
Expansion & Upsell
Land & Expand. Leverage Success. Grow Naturally.
Purpose-built for CSMs, AMs, and anyone driving NRR. Turn existing success into expansion opportunities. Make growth feel like the natural next step, not a new sale.
"The best expansion doesn't feel like upselling. It feels like helping them get more of what's already working."
— Account Management Wisdom
Expansion Signals to Watch
| Signal | What to Look For | Your Action |
|---|---|---|
| Team Growth | Hiring in departments using your product | Proactive reach-out about scaling |
| Usage Milestone | Hit a limit or achieved strong results | Celebrate and explore next level |
| New Initiative | Announced strategy that aligns with your expansion | Connect initiative to expanded capability |
| Renewal Approaching | 60-90 days before contract renewal | Bundle expansion into renewal conversation |
The Philosophy
Expansion selling is fundamentally different from new business. You're not convincing someone to trust you—they already do. The question is whether they're getting all the value they could from the relationship.
The key insight: lead with their success, not your product. When you celebrate what they've achieved and connect expansion to getting even more of that, it doesn't feel like an upsell. It feels like the obvious next step.
Key Characteristics
- →Lead with their success. Use their data, their results, their story as the foundation.
- →Natural next step framing. Expansion should feel like continuation, not new purchase.
- →Watch for signals. Team growth, usage milestones, new initiatives, renewals.
- →Help them build the case. Give champions the ammo to sell internally.
- →Trusted advisor tone. You're helping them get more value, not selling more stuff.
When to Use
Best For
- • Happy customers seeing strong results
- • Accounts approaching usage limits or milestones
- • Teams that have grown since initial purchase
- • Renewal conversations with expansion potential
Avoid When
- • Customer isn't seeing value from current product
- • Relationship is rocky or trust is damaged
- • They're not fully using what they have
- • No clear trigger or need for expansion
The Prompts
Expansion Email
Write an expansion/upsell email to an existing customer. Context: - Customer contact: [NAME], [TITLE] at [COMPANY] - What they currently use: [CURRENT PRODUCT/TIER] - Results they've achieved: [METRICS/OUTCOMES] - Expansion opportunity: [ADDITIONAL PRODUCT, SEATS, TIER] - Trigger: [Why now - team growth, initiative, results milestone] Expansion Email Rules: - Lead with THEIR success, not your product. - Use their own data/results as the proof point. - Frame expansion as the natural next step, not a new purchase. - Connect to something that's changed (team size, goals, usage). - Make it feel like you're helping them get more value, not selling more. - Reference specific results they've seen. - Position new capability as unlocking even better outcomes. - Clear, low-friction next step. - Under 100 words. Celebratory, not salesy. Tone: Helpful, celebratory of their success, consultative. Like a trusted advisor seeing an opportunity.
Expansion Discovery Questions
Generate expansion discovery questions for an existing customer. Context: - Customer: [COMPANY] - Current usage: [WHAT THEY USE TODAY] - Results achieved: [OUTCOMES/METRICS] - Potential expansion: [WHAT YOU WANT TO SELL] Expansion Discovery Approach: SUCCESS VALIDATION - What results have you seen since implementing? - How has [your product] changed how your team works? - What would you tell a peer about your experience? EVOLUTION OF NEEDS - What's changed in your business since we started working together? - Are there new teams or use cases that have come up? - What challenges have emerged as you've grown? EXPANSION SIGNALS - Are there other teams who could benefit from what you're seeing? - What would you do with [expanded capability]? - Where are you hitting limitations with your current setup? TIMING & STAKEHOLDERS - Is this something you'd want to explore this quarter? - Who else should be part of this conversation? - What would need to happen to make this a priority? The best expansion conversations start with their success, not your pitch.
Expansion Objection Handling
Handle this objection in an expansion conversation. The objection: [PASTE OBJECTION HERE] Context: - What they currently use: [CURRENT PRODUCT/TIER] - Their results so far: [SUCCESS METRICS] - Expansion being proposed: [ADDITIONAL PRODUCT/SEATS/TIER] Expansion Objection Framework: - "Budget isn't approved" = Help them build the business case from current ROI - "We're not using what we have" = Understand why, solve adoption first - "Not the right time" = Establish future trigger, stay in touch - "Need to involve others" = Offer to help make the case Generate: 1. Acknowledgment that validates their concern 2. Reference to the success they've already seen 3. Question to understand the real blocker 4. Offer to help (not push)
LinkedIn Message
Write a LinkedIn message to expand within an existing account. Context: - Contact: [NAME], [TITLE] at [COMPANY] (existing customer) - Relationship: [YOUR CURRENT ENGAGEMENT] - Expansion angle: [WHAT YOU WANT TO DISCUSS] - Their recent success: [SPECIFIC RESULT/MILESTONE] Expansion LinkedIn Approach: - Lead with genuine congratulations on their success. - Reference something specific to their results. - Introduce the expansion idea as a thought, not a pitch. - Make the ask a conversation, not a commitment. - Under 50 words. Warm, helpful, not salesy. Tone: Trusted partner sharing an idea. Celebratory first.
Expansion Business Case Builder
Build an expansion business case for this customer. Context: - Customer: [COMPANY] - Current product/tier: [WHAT THEY HAVE] - Results achieved: [CURRENT ROI/OUTCOMES] - Proposed expansion: [ADDITIONAL PRODUCT/SEATS/TIER] - Expansion cost: [PRICE OF EXPANSION] Generate an Expansion Business Case: CURRENT VALUE SUMMARY - What they're paying today - Results/ROI they've achieved - Key metrics that have improved EXPANSION OPPORTUNITY - What the expansion includes - What new capabilities it unlocks - Which teams/use cases it serves PROJECTED VALUE - Expected additional ROI - New metrics that would improve - Time to value for expansion THE MATH - Current investment: $X - Current ROI: Y% - Expansion investment: $Z - Projected additional ROI: W% - Net value increase: $N WHY NOW - What's changed that makes this timely - Cost of waiting - Competitive/market considerations NEXT STEPS - Who needs to approve - What information they need - Proposed timeline Make it easy for your champion to sell internally.
Example Output
Subject: Congrats on the 47% improvement Sarah, Just saw your Q3 numbers come through—47% improvement in meeting rate since you started with us in June. That's legitimately impressive. Quick thought: your SDR team has grown from 5 to 12 since then. The research workflows that worked at 5 often need tuning at 12+ (different ramp challenges, coverage gaps, etc.). We have a few things that help larger teams keep that quality bar high as they scale. Would it be useful to explore whether any of them fit where you're headed? — Marcus