Beyond the Upgrade: Using Windows 11 Migration to Introduce Microsoft 365 Upsells 

With Windows 10 having reached end-of-life, many businesses are scrambling to upgrade to Windows 11. For Managed Service Providers (MSPs), this moment presents a strategic opportunity to bundle Microsoft 365 upsells, especially Business Premium, into the migration conversation. 

Here’s how MSPs can turn a mandatory upgrade into a value-driven transformation. 

Why Windows 11 Migration Is a Strategic Moment 

Windows 11 isn’t just a prettier interface—it’s designed to work seamlessly with Microsoft 365, especially in security, productivity, and cloud integration. As clients prepare to upgrade, they’re already thinking about: 

  • Device refreshes  
  • Security improvements  
  • Remote work enablement  
  • Cloud-first strategies 

This mindset makes it the perfect time to introduce Microsoft 365 Business Premium as part of a bundled solution. 

Bundling Strategies That Work 

Instead of offering Windows 11 migration as a standalone service, MSPs should package it with Microsoft 365 Business Premium and other value-adds. Here are some example bundles: 

1. Essentials Bundle

  • Windows 11 upgrade  
  • Microsoft 365 Business Standard  
  • Basic endpoint security  
  • Email migration 

2. Secure Productivity Bundle

  • Windows 11 upgrade  
  • Microsoft 365 Business Premium  
  • Intune device management  
  • Defender for Business  
  • Conditional access setup

3. Enterprise Modernization Bundle

  • Windows 11 upgrade  
  • Microsoft 365 Business Premium  
  • Azure AD Premium P1  
  • Endpoint analytics  
  • Virtual CIO consultation 

Benefits of Bundling 

  • Simplifies decision-making for clients  
  • Increases recurring revenue  
  • Positions MSPs as strategic partners, not just IT fixers 

Repeatable Workflow for Migration + Upsell 

1. Assessment Phase  

  • Identify devices needing upgrade  
  • Evaluate current licensing and security posture 

2. Proposal Phase

  • Present tiered bundles with clear ROI  
  • Highlight Business Premium’s value: security, compliance, remote access 

3. Execution Phase

  • Perform migration  
  • Deploy Microsoft 365 services  
  • Configure policies and protections 

4. Post-Migration Opimization

  • Train users  
  • Monitor performance  
  • Offer ongoing managed services 

Why Microsoft 365 Business Premium? 

Business Premium is tailor-made for SMBs and nonprofits looking for enterprise-grade features without enterprise complexity: 

  • Advanced security: Defender for Business, Intune, Azure AD  
  • Productivity tools: Teams, SharePoint, OneDrive  
  • Compliance & control: Data loss prevention, conditional access 

It’s the perfect complement to Windows 11’s modern architecture. 

Educate, Don’t Just Sell 

Use this migration moment to educate clients on: 

  • The risks of staying on unsupported systems  
  • The benefits of cloud-first security  
  • The long-term value of integrated Microsoft ecosystems 

Position your MSP as a trusted advisor, not just a service provider. 

A Gateway of IT Transformation 

Think of the Windows 11 migration as a gateway to modern IT transformation. By bundling Microsoft 365 Business Premium into your migration offerings, MSPs can deliver more value, deepen client relationships, and grow recurring revenue. 

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