Career Roadmap
Career Roadmap
The education, training, roles, sales work, and founder work that shaped Benjamin's career.
Text version of the career roadmap, for accessibility and AI
Severna Park, Maryland. Origin and formationSeverna Park, MD, Roots. Where the course begins. The Maryland origin point of an eight year arc from operator to defense business development.
University of Maryland. EducationCollege Park, MD, 2014 to 2018, then 2023. An undergraduate degree and, later, a Project Management master's. This is the academic spine of program discipline.
Pensacola, Florida. Aviation and EW trainingNAS Pensacola, FL, 2018 to 2020. Combat Systems Officer and Electronic Warfare Officer training. This is the technical foundation the whole career is built on. Roles formed here: Undergraduate Combat Systems Officer Training (UCT). Skills formed here: Aviation fundamentals, Electronic warfare fundamentals.
Tucson, Arizona. EW mission systems and sales in parallelTucson, AZ, 2020 to 2023. Benjamin qualified as an electronic attack Weapons Systems Officer at the top of his class, ran current operations scheduling, then led IT and asset management that bridged operations and a next generation acquisition. He closed real estate deals on the side the whole time. Roles formed here: EC-130H Initial Qualification Training, Scheduling Officer, Officer in Charge, Information Technology Asset Management, Executive Sales Consultant. Skills formed here: Electromagnetic spectrum operations, Tactical employment, Crew resource management, Scheduling, Flying hour program, Resource synchronization, Cross unit coordination, Asset management, Program consolidation, Cybersecurity accounts, Vendor and contract coordination, Full cycle deal closing, Negotiation, Client advisory, Pipeline ownership.
Las Vegas, Nevada. ISR and RPA mission systems and leadershipNevada, USA, 2023 to 2025. Benjamin qualified on an advanced ISR remotely piloted aircraft mission, standardized enterprise planning, rebuilt the training enterprise with throughput up 54 percent, and led a 22 person flight across eight specialties. Roles formed here: RQ-170 Formal Training Unit, Assistant Chief of Tactics, Chief of Training, Assistant Flight Commander. Skills formed here: Crew resource management, Mission briefing and debriefing, Tactics development, Standardization, Technical writing, Program design, Process improvement, Training management, Data driven decisions, Mission planning, Threat analysis, Team leadership, Aircrew training.
Key Largo, Florida. Transition and founder baseKey Largo, FL, 2025 to present. The current base. SkillBridge transition to industry and founder of September Fair LLC, parent of ParksRadar, ChannelWake, and LegendHeading. Roles formed here: Founder and CEO, September Fair LLC. Skills formed here: Product judgment, Go to market strategy, Research driven product development, Brand and narrative positioning.
How to read the roadmap
Each point marks a phase in Benjamin's development: education, aviation and electronic warfare training, mission systems, leadership, sales, and founder work. Click a point to see what happened there, the roles connected to it, and the skills that formed.
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