Who is Gabby Macsweeney?
Gabby Macsweeney is the VP Marketing at LEGALFLY, the Belgian legal AI company. LEGALFLY is the legal operating system for in-house teams, founded in Belgium in 2023 by former AI leaders at Tinder.
About Gabby Macsweeney
Gabby runs marketing at LEGALFLY, which brings legal AI to the whole business, from contract review and drafting to due diligence and research.
About LEGALFLY
LEGALFLY is the legal operating system for in-house teams, founded in Belgium in 2023 by former AI leaders at Tinder. Its customers include the European Commission, SAP and Lufthansa. It grew more than 800% in 2025, according to its CEO, and has raised more than €17M, including a €15M Series A led by Notion Capital with Redalpine and Fortino Capital.
Why Gabby is on the cover
LEGALFLY grew eightfold last year selling legal AI to the whole business, not just the legal team, and Gabby runs its marketing.
Questions about Gabby and LEGALFLY
- What does Gabby Macsweeney do at LEGALFLY?
- Gabby Macsweeney is the VP Marketing at LEGALFLY, the Belgian legal AI company.
- What does LEGALFLY do?
- LEGALFLY is the legal operating system for in-house teams, founded in Belgium in 2023 by former AI leaders at Tinder.
- How much has LEGALFLY raised?
- LEGALFLY raised a €15M Series A led by Notion Capital and has raised more than €17M in all.

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