Upsell Maximizer

Your LTV amplifier - Maximize revenue from existing customers through strategic expansion

What This Agent Does

Your average order value is stuck at $50 and you need it at$ 75. You sell single products when customers would buy bundles. Your pricing tiers leave money on the table. You don’t know which products naturally go together. Your expansion revenue is 10% when it should be 30% of total revenue.

The Problem: Most companies leave 40-60% of potential revenue on the table by not systematically upselling and cross-selling. They don’t identify expansion opportunities, lack product recommendation logic, use ineffective pricing structures, and miss the window when customers are most likely to buy more.

The Solution: The Upsell Maximizer is your revenue expansion strategist who finds and captures additional revenue from existing customers. This agent identifies upsell opportunities and triggers, designs product recommendation logic based on purchase patterns, forecasts expansion revenue potential, tracks feature adoption as buying signals, creates cross-sell sequences with perfect timing, and optimizes pricing tiers to maximize revenue per customer.

This agent uses proven expansion frameworks from high-performing subscription and e-commerce companies to ethically increase customer lifetime value.

Quick Start

Find your expansion opportunities in 30 seconds:

# Identify upsell potential
/ask "Analyze our product catalog and identify upsell opportunities"

# The agent maps product relationships and expansion potential

Capabilities

Upsell Opportunity Identification

Find who’s ready to buy more and what to offer. The agent identifies upgrade triggers (usage hitting limits, feature requests), maps value thresholds where upgrades make sense, finds usage-based opportunities (you’re using 90% of your plan), designs tier migration paths that feel natural, and creates upgrade campaigns targeting ready customers.

Example: The agent identifies that customers on the Starter plan who use Feature X more than 20 times/month upgrade to Pro at 3x the rate of other Starter customers. This becomes an automated trigger.

Product Recommendation Logic

Show the right products at the right time. The agent designs recommendation rules based on purchase history, builds affinity matrices (customers who buy X also buy Y), creates bundle logic that increases AOV, implements purchase pattern analysis, and develops “frequently bought together” systems.

Expansion Revenue Forecasting

Model the impact of expansion strategies. The agent models upsell potential by customer segment, predicts upgrade rates based on behavior, calculates expansion MRR from campaigns, forecasts LTV improvements from better expansion, and tracks expansion metrics (expansion MRR, net dollar retention).

Feature Adoption Tracking

Use product usage to identify expansion opportunities. The agent monitors feature usage by customer and plan, identifies adoption gaps (they’re not using what they pay for), designs adoption campaigns to increase value perception, tracks feature value to prove ROI, and predicts churn signals from non-adoption.

Cross-sell Sequence Design

Create systematic cross-sell programs. The agent creates post-purchase sequences introducing complementary products, designs complementary offers based on initial purchase, builds timing triggers (30 days after purchase, after milestone), plans channel strategy (email, in-app, sales call), and tests offer combinations for maximum take rate.

Pricing Tier Optimization

Design pricing that captures maximum value. The agent analyzes tier performance and migration patterns, identifies pricing gaps (too few or too many options), designs value metrics that align to willingness to pay, tests price points for each tier, and optimizes tier packaging (features per tier).

When to Use

Use the Upsell Maximizer when you need to:

Increase average order value across your customer base
Design product recommendation systems
Build upsell and cross-sell automation
Optimize pricing tiers and packaging
Forecast expansion revenue potential
Identify which customers are ready to expand

Example Workflows

Workflow 1: Upsell Opportunity Analysis

Find expansion potential in your base:

# Step 1: Analyze current state
/ask "Analyze our customer base and identify upsell opportunities"

# The agent will examine:
# - Current revenue mix (by tier/product)
# - Upgrade patterns (who upgrades, when, why)
# - Usage patterns vs. plan limits
# - Feature requests by segment
# - Competitor comparisons

# Step 2: Get prioritized opportunities
# Agent identifies:
# - High-potential segments (Starter users hitting limits)
# - Quick wins (low-effort, high-impact)
# - Revenue potential per opportunity
# - Implementation difficulty

# Example output:
# 1. Auto-upgrade customers at 90% of plan limit → $47k/yr
# 2. Cross-sell Product B to Product A users → $32k/yr
# 3. Introduce middle tier between Starter/Pro → $28k/yr

Output: Prioritized opportunities with revenue estimates and implementation plans.

Workflow 2: Product Recommendation System

Build “customers also bought” logic:

# Design recommendation engine
/ask "Create product recommendation logic for our catalog"

# The agent builds affinity matrix:

# Product A → Recommend:
# - Product B (37% of buyers also buy within 30 days)
# - Product C (28% of buyers also buy within 60 days)
# - Product D (15% of buyers also buy within 90 days)

# Product B → Recommend:
# - Product E (42% affinity)
# - Product A (37% affinity)

# Also creates:
# - Bundle offers (A + B + C = 20% discount)
# - Timing triggers (when to show recommendation)
# - Placement strategy (cart, email, product page)
# - A/B test recommendations

Output: Complete recommendation system with rules and implementation guide.

Workflow 3: Pricing Tier Optimization

Fix your pricing structure:

# Optimize pricing
/ask "Analyze our pricing tiers and recommend optimization"

# The agent analyzes:
# - Current tier distribution (how many per tier?)
# - Upgrade/downgrade patterns
# - Revenue per tier
# - Feature usage by tier
# - Competitor pricing comparison

# Identifies issues:
# - 78% of customers on cheapest tier (need better middle tier)
# - Big jump from Starter ($29) to Pro ($99) (need bridge tier)
# - Top tier underutilized (need better differentiation)

# Recommends:
# - Add $49 "Growth" tier between Starter and Pro
# - Repackage features to create clear value steps
# - Test new price points on new customers
# - Grandfather existing customers (or migrate with incentive)

Output: Pricing optimization plan with tier structure and migration strategy.

Workflow 4: Cross-sell Campaign

Create automated cross-sell sequences:

# Design cross-sell automation
/ask "Create a cross-sell sequence for customers who buy [Product A]"

# The agent designs campaign:

# Trigger: Purchase of Product A

# Day 3: Education email
# - Subject: "Getting the most from [Product A]"
# - Content: Best practices, tips, use cases
# - Soft mention of Product B for advanced users

# Day 7: Case study
# - Subject: "How [Customer] achieved [Result]"
# - Content: Customer using A + B together
# - CTA: Learn about Product B

# Day 14: Direct offer
# - Subject: "Take [Product A] to the next level"
# - Content: What Product B adds
# - Offer: 20% discount for existing customers
# - Urgency: 7-day expiration

# Day 21: Last chance
# - Subject: "Your exclusive offer expires tomorrow"
# - Content: Reminder of benefits
# - Social proof: "487 [Product A] users upgraded"

# Non-converters: Exit to regular nurture

Output: Complete cross-sell sequence with timing, copy, and logic.

Best Practices

Time It Right: The best time to sell more is right after a customer gets value. The agent identifies these “win moments” and triggers offers then.
Make It Obvious: Customers shouldn’t have to guess what to upgrade to. Use clear pricing pages, in-app upgrade prompts, and usage-based notifications (“You’re at 90% of your limit”).
Bundle Intelligently: Products that are frequently bought together should be offered as discounted bundles. The agent identifies natural bundles from purchase data.
Grandfather Carefully: When changing pricing, decide whether to grandfather existing customers. The agent recommends based on revenue impact vs. customer satisfaction risk.
Track Net Dollar Retention: The key metric is NDR (Net Dollar Retention). Above 100% means expansion exceeds churn. World-class is 120%+. The agent helps you track and improve this.
Don’t Be Pushy: Expansion should add genuine value. The agent designs ethical upsells that help customers achieve goals, not manipulative tactics.

Output Reports

The agent organizes outputs at:

Reports: reports/upsell/upsell-maximizer-{date}-{strategy-slug}.md

Reports include current state analysis, opportunities, revenue forecasts, and implementation plans.

Funnel Architect - Post-purchase funnel optimization
Email Wizard - Upsell email sequences
Continuity Specialist - Retention before expansion

/ask - Query the agent for expansion strategy
/scout - Find customer and revenue data
/plan - Create comprehensive expansion programs