Seeking a highly organized, responsive, and entrepreneurial Executive Assistant based in the Kansas City area to support a busy real estate investor and entrepreneur across multiple ventures, primarily in real estate investment and management, aviation-related interests, and entrepreneurial initiatives. Jason Gilbert is the founder and CEO of Dutch Rocket https://dutchrocket.com/ and you'll be supporting him.
This role is ideal for someone who thrives in a fast-paced environment, enjoys ownership and operational impact, and wants the opportunity to grow into a larger role over time.
This position is fully remote but requires residency in the Kansas City metro area.
About the Role
This is not a traditional assistant position. You will serve as a strategic operations partner across several active ventures. The right person will bring structure, documentation, follow-through, and organization to a dynamic entrepreneurial ecosystem.
You will begin at approximately 20 hours per week as a 1099 contractor at $20/hour. For the right individual who proves reliability and impact, there is meaningful opportunity for increased responsibility, expanded hours, and financial upside.
High responsiveness is essential.
Core Responsibilities
Administrative & Organizational Support
Underwriting support (including SDA deal analysis)
Airbnb management oversight
Property management coordination
Forming new LLCs
Aviation Administration
Aviation tax coordination
Pilot logbook management
Entrepreneurial & Content Support
Support for Beyond Pulse / 360Agency initiatives
Dutch Rocket newsletter coordination
Burnout to Buyout project support
VC peer group coordination
Ideal Candidate Profile
Kansas City metro-based (required)
Highly responsive and dependable
Detail-oriented and systems-minded
Comfortable working independently with minimal oversight
Strong written communication skills
Excel / Google Sheets proficiency
Familiarity with real estate processes preferred
Entrepreneurial mindset — enjoys building and improving systems
Discretion and confidentiality are non-negotiable
Bonus if you:
Have experience underwriting real estate deals
Have supported founders or investors
Have experience with LLC formation or bookkeeping
Have aviation industry familiarity
What This Role Offers
• Fully remote, flexible schedule
• Direct access to a founder/operator
• Exposure to real estate investing, aviation, and entrepreneurial ventures
• Opportunity for expanded scope and financial upside as trust and performance grow
• Real ownership and impact — not just task execution
Principals only. Recruiters, please don't contact this job poster.