Chief Executive Officer at Jettly and BlackJet.
I build companies focused on improving access to private aviation through technology, operational excellence, and customer experience.
Over the last ten years, I have led initiatives across commercial growth, sales, operations, and product strategy while expanding access to private jet charter and membership solutions globally.
I am also a commercial pilot which gives me firsthand operational perspective in an industry I have spent my career helping modernize.
Focus areas: Private Aviation • Aviation Technology • Marketplace Platforms • Membership Models • Customer Experience • Growth
Company: Jettly
We are thrilled to have you join us today, welcome to ValiantCEO Magazine’s exclusive interview! Let’s start off with a little introduction. Tell our readers a bit about yourself and your company.
Justin Crabbe: I’m Justin Crabbe, a commercial pilot and an aviation technology entrepreneur with more than a decade of experience driving innovation and modernization in private aviation. As the Founder and CEO of Jettly and BlackJet, I have launched more than 50 e-commerce stores, software-as-a-service products, and mobile app platforms. My firsthand cockpit experience gives me a practical view of what it takes for private travel to work well.
Jettly was launched in 2016 in response to a simple but disruptive idea: private aviation should not feel like an opaque call followed by numerous callbacks, but like a searchable, transparent marketplace. I saw the challenge of relying on manual brokerage, limited pricing visibility, and a high-friction booking process among travelers and operators, and it inspired me to change that model through Jettly. Today, Jettly aims to make private aviation feel more like Expedia for private aircraft, with desktop and mobile platforms that let travelers search for charter flights using detailed filters in minutes. It provides travelers with access to more than 23,000 aircraft from vetted operators across 190 countries worldwide.
What was the moment you realized that complexity was holding your company back, and how did that shift your approach to product, operations, or strategy?
Justin Crabbe: As a commercial pilot, I know aviation is inherently complex, but when I saw people buy private flights, I realized there’s another layer of complexity that needs addressing. I encounter passengers who send a charter request and then wait a long time for a follow-up call from brokers and operators. The back-and-forth conversation doesn’t end there; both parties then have to wait for collected quotes and pricing before anyone makes a decision. The complexity of coordinating aircraft availability, operator networks, scheduling, positioning, pricing, and individual travel requirements spills into the booking process, leaving customers to navigate multiple conversations just to find the right flight.
I wanted to change that process and introduce a more open and transparent way of buying private flights, much like how people book their commercial airline tickets – there’s transparency involved. Every extra step in the traditional booking process costs customers confidence, and it was time to remember that customers aren’t expected to understand every operational detail; it’s our job to simplify the process behind the scenes.
From there, I started to ask what it would look like if it were as easy as booking any other trip. That was the starting point of building Jettly, and everything since – from instant pricing to technological advancements in the app – came from that question.
Can you share one specific example of something you simplified (a product feature, process, pricing model, or customer experience) that delivered outsized results?
Justin Crabbe: We simplified private jet discovery and charter matching through Jettly’s digital marketplace. Everything a traditional broker does is included in the platform, just better and more enhanced. We brought that discovery process into a more streamlined digital experience. They can search for private flights, request quotes, negotiate prices, and discuss schedules and other travel requirements on a single platform. Even better, we took that approach a notch higher by integrating advanced technologies like Smart Match™, an AI workflow that matches and generates a shortlist of suitable, priced options in less than 24 hours.
How do you systematically identify and eliminate complexity across the organization without oversimplifying in ways that hurt quality or value?
Justin Crabbe: The customer journey is always our top priority. We get their perspective, analyze their decisions, and understand their pain points. We want to identify which parts of the process don’t add meaning or value to their overall experience. We use the data we collect to determine whether we need to adjust the system and whether signals suggest complexity may be working against us. Safety, operator vetting, and regulatory compliance are non-negotiable. Removing those is never an option, so we find ways to simplify how we present them to customers.
I also advise my team to distinguish between complexities essential to delivering reliable service and those that exist because of legacy processes or organizational habits. Our human advisors and the technology we integrate should go hand in hand. One should not exist without the other, especially for complicated and high-stakes trips that need human intervention and analytical thinking.
What’s the biggest resistance you’ve faced when pushing for radical simplicity, and how did you overcome it?
Justin Crabbe: The assumption of having a sophisticated service equates to a more complicated customer experience is one of the biggest challenges we’ve faced so far. But that’s not the reality of the business. People would think that you automatically need an expert just because it is complicated, and even some people in the industry would go as far as seeing transparency as a threat. Some customers would expect the old way of chartering private flights, and we would encounter some pushbacks from some operators on how we do things. But I’ve found that arguing doesn’t change minds, but showing does. When operators saw a simpler flow bring them more qualified demands and customer realizes the process helps them save time, the conversation shifted to “why change” to “how else can we simplify more”. That kind of resistance and realization at the end shows that actual proof beats persuasion every time.
For other CEOs who struggle with feature bloat, process overload, or confusing customer journeys, what’s the most important principle or first step you would recommend they take?
Justin Crabbe: As the old saying goes, always put yourself into someone else’s shoes. Walk through your product or service as a first-time customer and note every point of friction. Don’t try to solve every problem at once; pick one, remove it completely, then add a new feature or offering. When I first built Jettly, I talked to customers and passengers to understand how hard it was to access private flights, and I did the same with aircraft operators. They see their unused aircraft at an airport and start thinking about how people can access them more efficiently. You examined the situation through another person’s lens, identified the hurdle, and started designing a solution. Listen to what customers are saying, observe how they use your product and service, and challenge their assumptions by providing solutions. Technology is your best friend – use it to your advantage. Advanced tools shouldn’t just give more people capability; they should make the capabilities they need easier to access.
