sboghossian Unlock — Contextual Upsell
When this applies
This skill governs all upgrade prompts shown to users who encounter a capability gate — a feature, limit, or workflow that requires a higher plan. It fires when:
- Free tier hits feature gates:
- Deep research mode (multi-step legal research) → "Available on Pro"
- More than X queries/day → "Upgrade for higher limits"
- eFirm features (firm KB, matter management, RAG over firm documents) → "Available on Business plan"
- Word plugin → "Pro+ feature"
- Advanced drafting (multi-clause SPA, complex commercial) → "Pro recommended"
- Starter plan approaching credit limit — warn at 80% and 95% usage
- Pro plan hitting business-feature usage — e.g., attempting multi-user matter isolation
Behavior
Standard pattern
When the gate is hit, show exactly this pattern — no improvisation:
[Feature you wanted] is available on [Plan].
Get [X specific benefit] for $[Y]/mo.
[Upgrade →] [See all plans] [Maybe later]
The feature name must match exactly what the user just tried. Generic "upgrade for more features" is ineffective and feels disconnected.
Prompt construction rules
1. Name the specific blocked feature
- Wrong: "Upgrade for more capabilities."
- Right: "Deep research mode — multi-step legal research across Westlaw and Lexis — is available on Pro."
2. Lead with the benefit, not the price
- Wrong: "Pro plan is $79/mo."
- Right: "Get unlimited queries and deep research for $79/mo."
3. Show real ROI where possible
- "Pro users draft NDAs 3× faster with the firm KB integration."
- "Average Pro user saves 5 hours/week vs drafting manually."
- Match the ROI claim to the specific feature that was blocked.
4. One clear call to action
- Primary CTA: "Upgrade →" (direct link to checkout for the recommended plan)
- Secondary: "See all plans" (comparison page)
- Dismiss: "Maybe later" (session-level suppress; respect immediately)
Calibration rules — critical
When NOT to push an upgrade prompt:
| Condition | Action |
|---|---|
| User is in distress (see [[conversation-empathy-b2c]]) | Suppress prompt entirely; address the issue first |
| Less than 10 minutes since signup | Suppress; give value first |
| User already hit "Maybe later" this session | Suppress for the remainder of the session |
| User has seen 3+ prompts in the last 7 days | Suppress; frequency capping applies |
| User is in the middle of a critical task (signing deadline) | Complete the task first; prompt after |
When to push HARDER:
| Condition | Behavior |
|---|---|
| User just completed a high-value task (drafted 12-page MSA) | Higher-intensity prompt: name the specific time saved |
| User hit the same gate 3+ times in one session | Increase urgency: "You've hit this limit 3 times today." |
| User's heavy usage day | Prompt at end of session with daily summary of value created |
| User is actively browsing pricing page | Trigger in-session prompt via chat |
Conversion triggers (where to place extra effort)
- Post-high-value-task prompt — immediately after the user finishes a complex task where they can feel the value delivered
- Repeated gate hit — 3+ gate hits in one session means the user is actively trying to use features beyond their tier
- Heavy usage day — many queries, multiple documents processed = intrinsic motivation exists
A/B testing parameters
The following elements should be A/B tested per cohort:
| Element | Variants |
|---|---|
| Copy intensity | Value-led ("save 5h/week") vs feature-led ("unlimited queries") |
| Discount offer | No discount / 20% off first month / "Try Pro free 14 days" |
| CTA label | "Upgrade now" vs "Start free trial" vs "Get Pro" |
| ROI framing | Hours saved / drafts completed / queries available |
| Timing | Immediately on gate hit / after task completes / at session end |
Track per variant: click-through rate, conversion rate, churn within 30 days post-upgrade.
Plan tier mapping
| Tier | Key limit | Upgrade target |
|---|---|---|
| Free | 5 queries/day; no firm KB; no deep research | Starter or Pro |
| Starter | 30 queries/day; limited document length; no eFirm | Pro |
| Pro | Unlimited queries; firm KB; deep research; Word plugin | Business |
| Business | All Pro + eFirm; multi-user; matter management | Enterprise |
| Enterprise | Custom; white-label; API access | N/A |
When showing the upgrade target, skip tiers where possible — free user should be prompted to Pro, not to Starter, unless the Starter plan genuinely meets their use case at a significantly lower price point.
Localization for MENA
- Prices should display in USD by default; offer toggle to AED, SAR, or LBP if user jurisdiction is detected
- MENA users are more receptive to "save time" framing than "save money" framing in professional contexts
- WhatsApp handoff: offer "Continue on WhatsApp" alongside upgrade CTA — MENA users may want to upgrade via WhatsApp with a human sales agent for Business/Enterprise plans
Do not
- Never push upgrade during a user distress moment
- Never push more than once per day (frequency cap)
- Never say "this feature is not available" without immediately showing the path to unlock
- Never show a generic "upgrade for more" message — always tie to the specific blocked feature
- Never mock up or imply a feature is broken — clearly state it is a tier gate
Examples
Good — deeply contextual:
"Multi-document comparison is a Pro feature. With Pro, you can compare up to 10 contract versions side by side, saving ~2 hours of manual line-up. $79/mo. [Upgrade →] [Maybe later]"
Bad — generic and disconnected:
"You've reached your limit. Please upgrade to continue using Louis."
Related skills
- [[unlock-case-study-relevant-to-user]] — surface before upgrade prompt to prime with social proof
- [[unlock-empty-state-suggestions]] — starter suggestions for free-tier users who haven't hit a gate yet
- [[unlock-cross-product-bridge]] — bridge between product tiers (Justinian → Louis → Enterprise)