StretchLearn Course

Grow revenue from the customers you already won

A hands-on course on timing, pricing and building upsell and cross-sell plays across the journey, with real frameworks and named tools.

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Beginner9 hr 30 minSelf PacedRegistered

Course Overview

What this course is designed to develop

McKinsey estimates that personalized cross-sell can lift revenue by 10 to 30 percent, and Amazon has credited roughly 35 percent of its sales to its recommendation engine, yet most teams bolt random add-ons onto checkout and call it a strategy. This course teaches expansion revenue as a discipline: how to size the opportunity, pick offers that genuinely help the customer, and deploy upsell and cross-sell plays across onboarding, usage milestones, renewals and support. Every module uses named frameworks, real tools such as Shopify, HubSpot, Gainsight and Stripe, and worked examples so you ship working plays, not just theory.

Learning Outcomes

What the learner should be able to understand, build, or execute.

Distinguish upsell, cross-sell, bump and downsell and choose the right move for each moment

Calculate attach rate, average order value, expansion revenue and net revenue retention from raw data

Map upsell and cross-sell triggers to specific stages of the customer journey

Design good-better-best pricing and bundles using anchoring and the decoy effect ethically

Build product recommendation and post-purchase upsell flows in tools like Shopify and HubSpot

Run expansion experiments and report impact in revenue per account rather than vanity metrics

Curriculum Preview

Inside the curriculum: a structured path from fundamentals to execution.

Preview the course structure, see how the modules build on one another, and understand the path this program is designed to take you through.

Module 1

Module 1: The Economics of Selling More to Existing Customers

Before you design a single offer, you need to understand why expansion is the highest-leverage revenue work and how to measure it honestly. This module covers the definitions, the math, and the metrics that prove it works.

3 lessons

Upsell, Cross-Sell, Bump and Downsell, Clearly DefinedContent · 45 min

Preview Enabled

Why Expansion Is the Cheapest Revenue You Will Ever EarnContent · 45 min

LMS Access

The Metrics That Prove Expansion WorksContent · 50 min

LMS Access

Module 2

Module 2: Finding the Right Offer for the Right Customer

Great expansion is matching, not pushing. This module covers how to discover which products pair, segment customers, and build a recommendation logic that feels helpful rather than greedy.

3 lessons

Affinity Analysis: Discovering What Actually PairsContent · 50 min

LMS Access

Segmenting So the Offer Fits the PersonContent · 45 min

LMS Access

Building Recommendation Logic That Feels Like HelpContent · 45 min

LMS Access

Module 3

Module 3: Timing and Placement Across the Customer Journey

The same offer succeeds or fails based on when and where it appears. This module maps upsell and cross-sell moments to the journey, from checkout to renewal.

3 lessons

The Map of Expansion MomentsContent · 50 min

LMS Access

Winning at Checkout and Post-PurchaseContent · 45 min

LMS Access

Expansion in Subscriptions and Account-Based SalesContent · 50 min

LMS Access

Module 4

Module 4: Pricing, Bundling and Continuous Improvement

The pricing psychology and packaging that make upgrades feel like good deals, plus the experimentation discipline to keep improving. This module turns tactics into a durable system.

3 lessons

Pricing Psychology: Anchoring, Decoys and Good-Better-BestContent · 50 min

LMS Access

Bundling and Packaging for Higher Order ValueContent · 45 min

LMS Access

Testing, Measuring and Scaling Your Expansion ProgramContent · 50 min

LMS Access

Built for Application

A complete learning path, not a one-off inspiration hit.

This program is designed around progression: focused lessons, structured modules, applied resources, assessments, and a course rhythm that turns information into usable capability.

upsellingcross-sellingexpansion revenueaverage order valuenet revenue retentionproduct recommendationspricing and bundlingcustomer lifetime value