
How Justin Crabbe built Jettly around trust and transparent private charter
Justin Crabbe is CEO & Founder of Jettly, a private aviation marketplace connecting travelers with aircraft operators. The conversation explores why the company chose a technology-led marketplace, how it earns trust through operator relationships and human support, and what that taught Crabbe about scaling in a high-trust industry.
In a high-trust industry, technology can make the process more efficient and transparent, but it cannot replace human support. Jettly’s hybrid approach combines digital tools with people who can address customer concerns and help manage changes.
What’s the short story of how your business started, and what makes it genuinely different from the other options your customers have?
Jettly grew out of keen observation and personal frustration with traditional private aviation’s opacity. As a commercial pilot who spoke with charter operators, I realized no digital platform let travelers research and compare flights across operators. I saw a middleman-heavy industry dominated by hidden markups, confusing jet card commitments, and vague pricing structures, and I thought: if technology can revolutionize commercial travel and hotel booking, what’s stopping private charters from doing the same? Instead of back-and-forth phone calls, manual quotes, and heavy legacy commissions, we can build a real digital marketplace, like Uber or Airbnb for private jets, that connects travelers directly with vetted aircraft operators. So we built that platform. Today, Jettly gives travelers access to more than 23,000 aircraft in 190 countries and territories, with the same ease you’d expect when booking a hotel.
Jettly is a digital marketplace and does not own a fleet — and it was a deliberate strategy. We don’t try to fill any planes because we aren’t tied to our own aircraft; instead, we find the right aircraft at the right time and price for each requested trip. We have direct relationships with operators and aircraft owners, and our membership model gives customers wholesale pricing without commission on every booking. We also have a team across time zones ready to assist passengers 24/7 with changes and disruptions.
How did you win your first customers, and where does most of your new business come from today?
Winning our first customers and earning the trust of vetted operators and aircraft owners go hand in hand. One can’t happen without the other, so in Jettly’s early years, we focused on building client relationships and maintaining the credibility of the operators we onboarded. We targeted frequent flyers and corporate travelers who wanted a different and better approach to private charter. We offered a clear, low-cost alternative and invested more in technology and brand visibility to build trust and earn word-of-mouth recommendations.
A good portion of our clients today come from repeat flyers and referrals, which are good indicators that you’re delivering. New business still comes from combinations of digital acquisition, organic search, and strong client referral loops.
What’s one decision that changed the direction of your business, and one mistake that taught you the most?
Building Jettly as a technology-driven marketplace, rather than simply operating within the traditional charter brokerage model, was a pivotal decision for the business. My background and exposure to the industry and its legacy systems helped us gain a better perspective and changed how we approached the business. We don’t just facilitate individual charter requests; we’ve invested in technology to improve the entire process, from discovery and aircraft matching to pricing, availability, and booking.
One important realization I had while scaling the business was that I underestimated the value of the human touch for customers. I assumed that if technology was excellent, the experience would sell itself. But I was humbled when I realized customers don’t trust chatbots, especially when they have concerns; they want real human connection, someone who can address it in minutes. We then pivoted to a hybrid approach where technology augments the human connection and expertise. The former handles the efficiency and transparency, while the latter ensures flawless execution and client retention.
What has changed in your industry or in what your customers expect over the last couple of years, and how have you adapted?
We’ve seen a major shift in customer demographics and expectations since we built Jettly in 2016. We’ve seen a surge of first-time private flyers who differ from traditional customers: younger passengers, tech-savvy entrepreneurs, corporate teams, and large groups like families, who seek flexibility and operational efficiency when traveling. Anticipating further changes, we doubled down on our tech infrastructure and product ecosystem. We expanded our real-time quoting engine, streamlined instantaneous operator communications, and launched specialized features and services. We continue to strengthen our safety vetting protocols and ensure that every operator listed on our platform adheres to strict regulatory compliance and safety standards.
If you were advising someone starting out in your industry today, what would you tell them to do first, and what would you tell them to ignore?
My advice is to build trust before trying to scale anything. In aviation, or any high-value industry, trust is the primary currency that keeps the business running. Take the time to understand the operational realities of aircraft operators, the regulatory framework, and passenger pain points. Design a product and service that delivers transparent value and exceptional execution on every flight.
They can also ignore the temptation to copy legacy industry norms just because they’re the known standard, or because that’s how it’s always been. Take advantage of the growing trend and shifts in customer demand and demographics, and stay focused on what the modern end-user really needs and wants, rather than following outdated industry playbook rules.
Thank you to Justin Crabbe and the team at Jettly for sharing what actually worked with Leaders Perception readers.
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