Enhancing the Highspot Outlook integration

Surface Highspot content, deals, and meetings without leaving Outlook.

Year: 2025
Client: Highspot
Role: Lead Product Designer
Timeline: 10 months
Platform: Outlook (Web & Desktop)
Team: 1 PM, 1 Designer, 6 Engineers
Link: Microsoft AppSource

Outlook inbox with Highspot add-in docked in the right pane beside an open email — Highspot app docked beside the open email. No context switch.

Problem

Sales reps live in Outlook. The legacy add-in was little more than a file inserter, and every action opened a blocking iframe modal inside a ~320px pane. It couldn't scale to our big bet, “Highspot Everywhere,” or hit the FY26 MAU target.

Legacy Highspot Outlook add-in with Insert Content button opening a blocking iframe dialog — One action in a ~320px pane. Every insert opened a blocking iframe pop-up.

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