Expansion

Expand account value through systematic identification of upsell opportunities, properly timed offers, and clear presentations of additional value customers actually want.

Expansion

Introduction

Upselling isn’t about pushing harder. It’s about knowing when there’s a genuine next step that creates more value for the client. If you frame that well and time it right, it doesn’t feel like a pitch. It feels like good service.

In this playbook, you’ll learn how to build upsell ladders and simple deal expansion paths that make sense to the customer. These aren’t aggressive sales moves. They’re helpful, relevant offers that build on the work you’re already doing.

You’ll see how to structure and position these offers so they’re easy to say yes to—without damaging trust or adding pressure. When done well, upsells help both sides win. The client gets more value, and you grow the account in a sustainable way.

Chapters

1

How to identify expansion opportunities

Spot upsell and cross-sell opportunities from usage patterns, customer feedback, and lifecycle signals before customers even ask for more.

2

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.

3

How to structure cross-sell offers

Identify complementary products or services that solve related problems and present them at the right moment in the customer journey.

4

How to time expansion offers

Present upsells and cross-sells at renewal periods, usage milestones, and moments when customers naturally need more from your solution.

5

How to price expansion and growth

Structure pricing tiers, usage-based fees, and add-ons that enable customers to grow with you whilst capturing more value as they scale.

6

How to handle expansion conversations

Position upgrades and cross-sells as solving customer problems, not hitting your sales targets, so offers feel helpful instead of pushy.

Expansion

tools

HubSpot

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45

per month

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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100

per month

Customer.io

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

Amplitude

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61

per month

Amplitude

Product analytics for events, funnels and cohorts, useful when you need to see how users move and where they drop in product journeys.

Fireflies.ai

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18

per month

Fireflies.ai

Fireflies.ai transcribes meetings, extracts action items, and syncs notes to CRM with searchable meeting library for team collaboration.

Notion

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12

per month

Notion

Flexible workspace for docs, wikis, and lightweight databases ideal when you need custom systems without heavy project management overhead.

Books

Managing The Professional Service Firm

David H. Maister

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Managing The Professional Service Firm

A classic on leading expert teams. Balance sales, delivery and culture with numbers that keep the firm strong.

The 80/20 Principle

Richard Koch

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The 80/20 Principle

Use Pareto thinking to pick channels, ideas and customers. Cut the long tail and double down on what works.

Wiki

Units per invoice

The average number of units, seats, or items included on each invoice.

Invoices / contract

The average number of invoices issued per customer contract, reflecting contract length and billing frequency.

Related topic

Customer value

Acquiring customers is expensive. Keeping them is where margins improve. What would happen if none of your customers left? Build feedback loops, long-term relationships, retention programmes that reduce churn, and upsell frameworks that grow account value without being pushy.

Expansion

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