Overview
Paul Bennett is the founder of Cicero, a position held since October 2021[4]. Bennett has held multiple leadership roles across travel and sustainability sectors, including co-founder and CEO of Context Travel from October 2002 to February 2018[9], and currently serves as chair of the board of directors at Sustainable Travel International[5]. Bennett describes themselves as a three-time founder with background in marketing, technology, sales, and strategy[2]. Current advisory and board positions include roles at Airbnb as of January 2025[3], Context Travel[7], and Creative Contracts (Pty) Ltd[10]. Bennett holds an MA in Liberal Arts from St. John's College[11] and has completed certificates in Business Strategy from Harvard Business School[12] and Financial Modeling and Valuation Analysis from Corporate Finance Institute[13].
Profile introduction
I am a 3x founder/re-founder/CEO, board chair, and advisor with a deep background in travel, sustainability, and education. I've grown and exited businesses, and now consult with a range of executives, founders, and investors. I love working on tricky problems and figuring out innovative solutions. I have a strong background in marketing, technology, sales, and strategy, and am literate in finance and analytics. I co-founded Context Travel, a category-defining experiential travel company and certified B Corp that connects intellectually curious travelers with local experts for in-depth learni…
Career history
- AdvisorJan 2025 to presentAirbnb
- FounderOct 2021 to presentCicero
- Chair Of The Board Of DirectorsJun 2020 to presentSustainable Travel International
- Board MemberFeb 2019 to Jun 2020Sustainable Travel International
- Board MemberOct 2017 to presentContext Travel
- AdvisorMar 2018 to Jun 2020Context Travel
- Co-Founder & CEOOct 2002 to Feb 2018Context Travel
- Strategic AdvisorJul 2022 to presentCreative Contracts (Pty) Ltd
Education
- MA, Liberal Arts1996 - 1997St. John's College
Certificate, Business Strategy2022 - 2022Harvard Business School
- Certificate, Financial Modeling & Valuation Analyst (FMVA)2021 - 2022Corporate Finance Institute® (CFI))
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