Microsoft 365

Foster coherence across multiple apps for Microsoft's freemium upsell strategy.
  • Product Strategy
  • User Research
  • User Experience
  • Usability Testing
  • Siena Cairns
  • Rachel Park
  • Zoe Hawtoff
  • Figma
  • Principle
  • TURF Analysis
  • MaxDiff Analysis
  • 3 months


The freemium business emerged organically across different apps at different times. Because of this, our main challenge with Office 365 is that the premium value runs across a portfolio of apps and services, making it confusing for users to understand. Before tackling this project, the Office 365 free ecosystem:

  1. Lacked coherence across apps and services and how they ladder up to the Office 365 subscription
  2. Had no contextual narrative on what premium features to highlight during relevant user actions
  3. Had no feature prioritization strategy across various audience segments
  4. Did not outline the golden customer journey (from non-user to premium subscriber) across in-product touch-points
Previous Experience on OneDrive

Previous Experience on Outlook


To tackle this, the strategy team first conducted a full audit of our in-product approach today to understand the current customer journey, and note where there were gaps or opportunities for improvement in our messaging and visuals, and outlined goals for both.

Next, I worked with the strategy and research team to identify key questions we wanted to answer:

  • Which audiences are we trying to target in-product? How do we speak to each group differently to drive upsell?
  • Within each app, which features are spiking interest for users?
  • At what point within the free experience is a user most likely to engage with upsell messaging?
  • Which channels can we use to address our target audience in a meaningful way?

Co-Creation Workshop

Wanting to include potential users in the solution formation, our team ran four co-creation workshops where we asked participants to sketch and make notes regarding a productivity suite with their own package of feature across all products, both free and premium.


  • Establish trust and peace of mind. Microsoft is seen as a trustworthy, secure brand. Emphasize how Microsoft 365 does the hard work to organize the things that matter most.
  • Show tangible value. Package features that together, genuinely, feels like the subscription is “worth paying for.”
  • Talk about a personal hub. Like other consumer brands, users can integrate their everyday life into a wider Microsoft ecosphere.
Notes from various participants in co-creation workshop

User Journey

Lastly, with the audit and research that was conducted, I re-examined the customer journey flow by synthesizing four key stages in which messaging must be coherent, and created four different types of messaging strategies to be displayed in each stage, seen below:

First Run Experience

Previously, there was no introduction to what was available on the Microsoft 365 suite. Now, during each app’s first run experience, users get a brief overview on app-centric free and premium features, based on messaging that we developed with our co-design participants. Here’s OneDrive’s.


In-App Feature

Instead of unclear vague diamonds, now when users run into a paywall, they are met with an in-app feature callout that is relevant and easily dismissible. This minimizes interruption while slightly nudging users on premium capabilities that they may be interested in using.


Product Detail Pages

Following the technique of progressive overload, users are slowly introduced to more information the more they engage with upsell content, laddering up to the larger Microsoft 365 premium narrative.



Conducting A/B testing and a few months after our upsell redesign, we ran the numbers again and saw a significant increase in the following:

  • Engagement among free apps & services
  • Engagement with “Learn More” button when premium subscription pop-up appears
  • Conversion rates to premium subscription from free services

Due to privacy reasons, please contact me if you're interested in learning more about the quantifiable impact this project had!