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Courtney Dean

Director-level Product Manager specializing in AI, training, and performance assessment

FreelanceUniversity of West FloridaWoburn, MA20 Years ExperienceDirector Level

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About

Longtime Aptima product leader who turned a nominal DoD measurement 'suite' into a configurable cross-branch performance assessment platform deployed to Army, Navy, and Air Force users. Brings a rare mix of defense training, human performance science, AI/cybersecurity product work, and deeply user-centered UX thinking, including innovations like video tagging for live evaluation workflows.

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Key Strengths

  • Led end-to-end rebuild of a fragmented DoD assessment suite into an integrated platform
  • Strong product strategy grounded in mission alignment and reuse
  • Managed multiple coordinated roadmaps across platform components and integration efforts
  • Deep domain expertise in defense training and human performance measurement
  • Shipped products across Army, Navy, and Air Force units
  • Balances technical, UX, and organizational constraints to set product direction
  • User-centered design judgment that produced impactful workflow improvements
  • Applied AI/ML in cybersecurity through autonomous red-team agents with legal guardrails
  • Experienced in regulated and government environments with complex procurement hurdles
  • Effective cross-functional collaborator with engineering, design, science, and contracting teams
  • Strong talent assessment and mentorship, especially for nontraditional hires
  • Expertise in adaptive learning systems and human-centered educational technology

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Experience

Independent AI Product DevelopmentFreelance · Nov 2025 – Presentfreelance
Director of Product/ Principal Product ManagerAptima, Inc. · Jan 2019 – Oct 2025
Deputy Division DirectorAptima, Inc. · Jan 2018 – Oct 2019
Associate Division DirectorAptima, Inc. · May 2017 – Dec 2018
A-Measure Product LeadAptima, Inc. · Dec 2013 – May 2017
Senior ScientistAptima, Inc. · Aug 2012 – May 2017
ScientistAptima, Inc. · Oct 2006 – Aug 2012

Education

University of West Floridamaster, Industrial Organizational Psychology
Fort Hays State Universitybachelor, Psychology

Skills

Product ManagementCI/CDA/B TestingData AnalyticsOpenAIPrompt EngineeringAgentic AIProduct StrategyComputer VisionC#Multi-agent systemsBusiness developmentAI Product StrategyAI OrchestrationProduct Discovery

Languages

English

Certifications

Certified Product Manager – Association of International Product Marketing & ManagementCertificate in Software Product Management – University of Alberta via CourseraProduct Strategy – Kellogg School of Management, Northwestern UniversityAI Product Management – Duke UniversityCertified SAFe 5 AgilistChatGPT Prompt Engineer – Vanderbilt UniversityValue Creation Practitioner and Mentor – D'Amore-McKim School of Business at Northeastern University

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Courtney DeanDirector-level Product Manager specializing in AI, training, and performance assessment