Account expansion playbook for B2B SaaS

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.

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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.

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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.

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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.

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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.

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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.

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Expansion

tools

HubSpot

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

Rating

From

€

per month

Explore tool

My review

Customer.io

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

Rating

From

€

100

per month

Explore tool

My review

Amplitude

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

Rating

From

€

per month

Explore tool

My review

Fireflies.ai

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

Rating

From

€

per month

Explore tool

My review

Notion

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

Rating

From

€

per month

Explore tool

My review

Books

Managing The Professional Service Firm

David H. Maister

Rating

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

My review

The 80/20 Principle

Richard Koch

Rating

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

My review

Wiki

Units per invoice

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

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Invoices / contract

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

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Other playbooks

Demand generation tools

Pipeline doesn't fill itself. These tools help you identify who to target, reach them at scale, and create content that earns attention in crowded markets.

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Growth team tools

The wrong tools create friction. The right ones multiply your output without adding complexity. These are the tools I recommend for growth teams that move fast.

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Sales pipeline tools

Deals slip through cracks when your sales stack doesn't work together. These tools keep your pipeline visible, your follow-ups timely, and your process tight.

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Customer value tools

Acquiring customers is expensive. These tools help you keep them longer and grow their accounts so your acquisition costs actually pay off over time.

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Marketing funnel tools

Traffic means nothing if it doesn't convert. These tools help you capture leads, nurture them automatically, and understand what's actually working in your funnel.

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Hubspot configuration

HubSpot is powerful when configured properly and a mess when it's not. Set up your instance correctly from the start so your data stays clean and your team trusts the system.

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Expansion

Introduction

Chapters

1

How to identify expansion opportunities

2

How to design upsell paths

3

How to structure cross-sell offers

4

How to time expansion offers

5

How to price expansion and growth

6

How to handle expansion conversations

Expansion

tools

HubSpot

Customer.io

Amplitude

Fireflies.ai

Notion

Books

Managing The Professional Service Firm

The 80/20 Principle

Wiki

Units per invoice

Invoices / contract

Related topic

Customer value

Other playbooks

Demand generation tools

Growth team tools

Sales pipeline tools

Customer value tools

Marketing funnel tools

Hubspot configuration

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