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Sean Endler

Executive product and design leader specializing in SaaS, consumer, media, AI, and GovTech

Cleared For Takeoff, Inc.School of the Art Institute of Chicago21 Years ExperienceExecutive Level

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About

Product and design leader who has built AI-powered educational experiences in highly restricted U.S. government environments, including a virtual assistant for WARU supporting the Department of Defense acquisition workforce. Also built teams from the ground up at Legacy.com and has a strong track record of using user insight to simplify products and align AI with human expertise rather than replace it.

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Key Strengths

  • Shipped AI assistant for defense education platform within strict government security constraints
  • Strong human-centered AI philosophy focused on augmenting experts, not replacing them
  • Product and UX leadership across concept, experience, and design strategy
  • Balances AI capability with trust, accuracy, privacy, and compliance
  • Deep experience designing for education workflows with instructor oversight
  • Uses user research to materially redirect product strategy
  • Simplified complex live sports product into intuitive real-time mobile experience
  • Built multidisciplinary product, design, and engineering organization from scratch at Legacy.com
  • Cross-functional team builder who reduces silos between design and engineering
  • Mentor who grows contributors through ownership, critiques, and collaborative planning

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Experience

Chief Product Officer / PrincipalCleared For Takeoff, Inc. · Jan 2021 – Present
Head of User Intelligence, Design Research & User TestingNexstar Media Group · Jan 2019 – Jan 2021
Vice President of Design and Innovation LabLegacy.com · Jan 2014 – Jan 2017
Director User Experience and InteractionShopzilla · Jan 2012 – Jan 2013
Director User Experience and InteractionNapster · Jan 2010 – Jan 2011
Director Product DevelopmentMTV · Jan 2006 – Jan 2007
Central Design Group LeaderYahoo · Jan 2005 – Jan 2006
Senior Research and DevelopmentSony · Jan 1997 – Jan 2004

Education

School of the Art Institute of ChicagoVisual Communication
ArtCenter College of DesignProduct / Transportation Design

Awards

  • 11 patents - Sony Electronics
  • 1 patent - Yahoo!
  • The United States Department of Defense Presidents Award
  • Featured TEDx Department of Defense Design Innovation
  • Red Dot - Design Team of the Year / Sony Electronics
  • Red Dot - Sports Walkman S2 Personal Audio Line / Sony Electronics
  • Life Style Research, Body Zone / Sony Electronics
  • Life Style Research, VIAO / Sony Electronics

Languages

English

Certifications

Unauthorized Disclosure (UD) of Classified Information and CUIAnnual OSD Records and Information Management TrainingOPSEC (Operations Security) AwarenessIdentifying and Safeguarding Personally Identifiable Information (PII)Level I Antiterrorism Awareness TrainingCyber Awareness Challenge 2025Plug and PlayJuice JackingPrivacy Awareness

Publications

12 publications

Consumer electronicsConnected devicesUser experience designProduct designInterface systems

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Typically responds within 24 hours

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Sean EndlerExecutive product and design leader specializing in SaaS, consumer, media, AI, and GovTech