Ray Sisson
A result‑driven executive and serial entrepreneur, Ray Sisson brings a relentless focus on execution, revenue generation, and rapid scale to every venture he leads. As Managing Director of HMK USA LLC, and Chairman and CEO of Tailwinds Aviation Leasing, Ray has built his reputation on turning complex visions into tangible, profitable operations—no fluff, no delays.
Professional Snapshot
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Professional Snapshot
- Leadership & Execution:
- Established rigorous performance‑based milestones, ensuring every member of the leadership team—and every partner—delivers measurable results on schedule.
- Sales & Business Development:
- Drove annual revenue growth exceeding 150% year‑over‑year by securing strategic partnerships with top‑tier real estate developers, institutional investors, and municipal authorities.
- Personally negotiated and closed more than $500 million in franchise, licensing, and joint‑venture agreements across North America and Europe.
- Capital Raising & Investment:
- Cultivated deep relationships with global private equity firms, sovereign wealth funds, and venture‑capital syndicates to ensure flexible, low‑cost capital stacks.
- Scalability & Growth:
- Grew companies from a few million in revenues into billion-dollar enterprises within a five-year span, demonstrating his unique ability to scale operations aggressively and sustainably.
- Enterprising & Expansion:
- Led groundbreaking ventures in aviation leasing and airport infrastructure development, both in the U.S. and internationally, innovating operational frameworks that have influenced industry standards.
- Pioneered scalable aviation investment models, creating sustainable business engines across continents while navigating complex regulatory and geopolitical environments. Pioneered an innovative co‑ownership model for mixed‑use developments, eliminating traditional HOA fees and unlocking new streams of recurring revenue for stakeholders.
- Strategic Vision & Pragmatism: Balances big‑picture growth strategies with disciplined financial controls to maintain profitability through all market cycles.
- Relentless Drive: Known for a “no‑excuses” culture—if a goal isn’t met, Ray demands root‑cause analysis and immediate corrective action.
- Network & Influence: Deep contacts among C‑suite leaders, government agencies, and industry influencers, translating into preferential access to prime development sites and regulatory fast‑tracking.
- Performance‑Based Leadership: Champions equity‑driven incentives that align executive teams and external partners with the company’s long‑term valuation goals.
