How to design upsell paths

Create clear progression from entry tier to premium offering so customers see the natural next step as they grow and need more value.

How to design upsell paths

Introduction

Upsells fail when the path isn't obvious. Customers don't know higher tiers exist, can't see the value difference, or face too big a price jump. Strong upsell paths show clear progression entry tier for getting started, mid-tier for growing teams, premium for enterprise needs. Each tier solves specific problems. Customers naturally outgrow their current tier and see the upgrade as solving new constraints. This chapter shows you how to structure tiers that create natural progression, communicate the value of each level, and make upgrading feel like the logical next step instead of an aggressive sales pitch.

Structure tiers that create natural progression clearly

Define clear value differences that justify tier pricing

Price tiers to make upgrading attractive without cannibalising

Communicate tier benefits as solutions to growing needs

Conclusion

Next chapter

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Playbook

How to expand revenue per customer

Acquiring new customers is expensive. Growing existing ones is profitable. Identify expansion opportunities from usage patterns and needs. Design clear upsell paths that feel natural, not pushy. Time offers to renewal cycles and milestones. Structure pricing that enables growth.

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How to expand revenue per customer
Tools

Relevant tools

HubSpot
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HubSpot

All in one CRM with marketing, sales and service, strong when you want one system that teams adopt.

Customer.io
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Customer.io

Customer.io sends targeted messages across email, SMS, and push notifications triggered by user behaviour and product data for SaaS companies.

Figma
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Figma

Collaborative design for interfaces and assets excellent for landing pages, ads, and prototypes when marketing and design need alignment.

Growth wiki

Growth concepts explained in simple language

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Pricing strategy

Determine how to charge for products and communicate value to maximise willingness to pay whilst remaining competitive and supporting desired positioning.

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Customer success

Proactively help customers achieve desired outcomes to drive retention and expansion by ensuring they extract maximum value from your solution.

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Health score

Combine usage, engagement, and satisfaction signals into one metric that predicts churn risk so customer success teams prioritise accounts needing intervention.