The People

Built by the people
who fly the mission

Pilots, insurance professionals, and technologists — a small team that has lived the problem it is solving.

Leadership

The operating team

Steve Fairbanks

Steve Fairbanks

CEO & Chief Aviation Officer

An accomplished technology entrepreneur with several successful exits and an ATP-rated professional aviator. Recipient of the AOPA Regional Instructor of the Year Award for his work in general aviation training, he holds Captain type ratings in the Phenom 300, Challenger 300/350, and Gulfstream 600.

Matt Friess

Matt Friess

Chief Insurance Officer

A business leader, insurance professional, and strategic advisor with more than 20 years of experience helping individuals, families, and businesses achieve their financial and operational goals, specializing in risk management and insurance planning. He earned his MBA from Texas Tech University's Rawls College of Business and a bachelor's degree from Oklahoma State University.

Gregory A. Miller

Gregory A. Miller

Chief Technology Officer

A technology leader who has spent 35+ years turning ambitious ideas into working systems, drawing on deep experience in the mortgage and financial services space. He specializes in API-driven integrations, intelligent automation, AI-powered applications, and cloud-native infrastructure, translating vision into the products and platforms that move a company forward.

Rob Berkland

Rob Berkland

Chief Financial Officer

A senior finance executive with more than 25 years leading accounting, treasury, and financial reporting across consumer, commercial, and asset-based lending. He has served as Chief Accounting Officer and Controller for organizations including Santander Consumer USA, overseeing financial controls during the company's IPO. He holds a B.S. in Accounting from Oklahoma State University and an Executive MBA from Southern Methodist University's Cox School of Business.

Fly with us

Enrollment opens in 2027. Join the waitlist and be first in line.

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