Elevate Aviation Group Founder and CEO Greg Raiff is taking a two-tiered approach to private aviation, with an instant booking app designed to entice new customers and Private Jet Services Group, its version of a private bank

@ 2023 Allie Burke Photography

You may never have heard of Elevate Aviation Group or Private Jet Services Group, although the two companies can trace their roots back several decades. PJS, as it is called, is well known to those who are charged with arranging sports teams and live entertainment tour charters.

Owner and CEO Greg Raiff is already well-known in business aviation. He now wants Elevate Jet to become a household name to a broader set of high-net worth consumers – those already flying private and the HNWs and corporates who have the means and need but have found the arcane process of booking ad hoc charter flights too much of a hassle with too much friction and too many letdowns.

Building a widely known consumer brand, such as NetJets, Wheels Up, VistaJet, or Flexjet, is easier said than done. Only a few companies have significant awareness outside the most regular private aviation users and even at that, many consumers stumble over the numerous similar sounding names in a long-tail industry that includes just three billion-dollar companies, only a few that have reached the $100 million sales mark, and a seemingly endless number of nice looking websites fronting for what is in some cases the proverbial broker working out of their basement and entrepreneurs with big dreams and little else.

Raiff, for his part, got his start selling spring break flights while still at Middlebury College in Vermont. He then founded Private Jet Services Group and built the company, organizing charter flights for political campaigns, sports teams, and live entertainment tours. Sports teams it has flown have won 27 NCAA hockey championships, 19 Major League Soccer titles, 17 NHL Stanley Cups, 12 NCAA football championships, 10 World Series, eight NCAA basketball championships, and three more college baseball titles. The music acts have won 139 Grammy Awards, 108 MTV VMAs, 85 Billboard Music Awards, you get the drift.

In January 2022, Raiff bought Keystone Aviation, a well-established aircraft management, charter, and maintenance operator, and in 2024, the company launched its rebranding under the Elevate banner.

Raiff may not have the same visibility to the broader public as Flexjet's Kenn Ricci, Vista's Thomas Flohr, or the halo that NetJets enjoys from Warren Buffett and its status from being part of Berkshire Hathaway; however, in the industry, he is known for not backing down.

That includes a lawsuit against Twitter, in which the company declined to pay outstanding invoices after Elon Musk bought what is now X. It was settled.

There was litigation against now-defunct iAero, in which PJS alleged that the operator of VIP jets used for group travel had bypassed an exclusive sales agreement, and PJS won a $29 million judgment. Raiff didn't get any money from that lawsuit when the airline filed for Chapter 7 bankruptcy; however, Raiff says he now has those clients he lost back.

More recently, PJS filed a lawsuit against Westchester County in New York, alleging that county airport officials stopped PJS from running group charter flights for members of the Yellowstone Club, while allowing Delta Air Lines to operate similar aircraft performing charter flights for the New York Rangers hockey team and the NBA's New York Knicks. That litigation is pending.

Raiff says, "If the facts are on your side and you've been wronged, the way that we do it in America to give us justice is by going to a court and asking for help, and that's what we've done."

In terms of making a bigger name for Elevate Jet, Raiff says his plans to achieve that objective don't include rolling up charter operators, billions of dollars in new jet orders, funding from private equity, or a public offering. Still, he expects privately held Elevate to grow its top line "from nine figures to ten figures" over the next several years.

Raiff is betting that nascent technology, driven by artificial intelligence and the company’s broad understanding of the complexities behind the scenes, will enable consumers on the front end to book ad hoc charter flights as easily as an Uber. He is also betting that high-net-worth consumer who have the finances to fly privately actually want to book their one-off charter flights online, not a given.

Stepping back, Raiff says the best way to think about Elevate Jet is to look at how big banks have bifurcated their offerings. They cater to those of us served by ATMs, apps and a banker who sits in a cubicle at the local branch while at the same time offering white glove private bank services to UHNWs from offices with wood-paneled conference rooms, and access to the specialist services typically reserved for a family office.

In terms of the instant booking play, Elevate Jet is not alone. It is one of more than a dozen companies that hope to digitize the process for booking ad hoc charter flights, much as Expedia or Travelocity have done for airline tickets.

Vista’s XO, Delta Air Lines-backed Wheels Up, broker OneFlight International, with endless television ads featuring NFL Hall of Famer John Elway and Shark Tank’s Robert Herjavec, private-equity backed FlyHouse, which has taken over high-profile football sponsorships previously used by Wheels Up, publicly traded Surf Air, and a half-dozen other players are all trying to provide a solution for what they see as a friction point for the industry.

It's also important to separate instant booking for ad hoc charters from online booking for fractional ownership and guaranteed jet card programs where customers are already in a program, know their price per hour, how far in advance they have to book, what type of jets they have access, how many passengers each type seats, where they can fly at their guaranteed rates, the list of extra charges, as well as the cancelation policy and more.

While democratization and instant charter flight booking gets a lot of press coverage, companies have been trying to make it work at scale since the early 2000s. Click to clunk, as it is called, refers to your mouse click from going to the website or app, getting a price, hitting the buy button, and getting your flight confirmed in the same session to the cabin door of your private jet, as it clunks shut.

Despite the crowded field, Raiff doesn’t believe it is a winner-take-all race. During a panel on technology at the Miami Corporate Jet Investor conference in November he told the audience, “Everyone who’s got Uber and Lyft on their phone got to a day they were leaving a concert or they were leaving an airport and Uber just kept cancelling and you’re waiting and you're waiting and you're waiting and finally you said, 'Okay, forget it I'm going to go download this Lyft thing that I know about and see if that comes, and for those of you that stuck with Lyft it's because Lyft showed up on a day at a moment in time when Uber couldn't deliver you a car reliably in that moment."

He predicted, "There will be an Uber of private jets. There will be a Lyft of private jets. There will also be three other competitors or 10 other competitors, and that’s fine. And consumers will make their own decisions for themselves."

All the click-to-clunk entrants are trying to take share from traditional brokers who currently control the market. It can take minutes to hours and even days for brokers to respond to a quote request, and after getting that quote, you have to figure out payment, which can often include putting a hold on your credit card while sorting out a wire transfer.

Reality in how it works often escapes the numerous press releases about booking charter flights online. Many brokers have interfaces that appear to let you book flights at confirmed pricing instantly. However, they are, in truth, lead generation tools. After entering your name, email, and phone number, you get an estimated price, and then, usually within minutes, your meeting or dinner is interrupted by a broker calling to gather more information and determine whether you are serious before they go out and actually find a charter jet you can book.

The Elevate Jet app, which officially launches tomorrow but can already be downloaded from the app store, allows you to book six types of aircraft, from turboprops and light jets to ultra-long-haul aircraft, so it offers categories rather than specific jet types. Its instant booking using dynamic pricing, meaning pricing is not fixed per hour. It changes based on routes, lead times, supply, and demand.

Raiff says you can currently book in the same regions as its fixed-rate jet card launched last year, covering the Continental U.S., most of the Caribbean, Mexico, and Central America. Sometimes prices will be higher, sometimes lower. You can also book transatlantic flights.

A nifty feature is that you can select the time you want to arrive, and the app will let you know when you need to depart. Raiff says the app helps guide users on how much luggage they can bring and notes whether they are choosing an aircraft that could require a fuel stop, as well as high-density airports that may charge an extra surcharge. He adds that charter jet sourcing follows the same "strict safety and vendor approval program…we utilize for our terrestrial bookings."

Raiff says the app will also serve as an entry point for the PJS side of the business.

"We had built out the private client group without ever building out the big box brand in front of it," Raiff says, adding, "And the thing about PJS as a private client group is that it's almost like a custom home builder. And so, there is no rate card."

While chartering ad hoc is often looked at as an entry-level solution, where once you get going, you move to a guaranteed jet card, and then to fractional ownership, and maybe even owning your own jet, Raiff says the PJS client could own their own jet or fractional share but prefer the private client approach.

"There are consumers that think that buying a fraction of a Challenger 3500 is the be-all, end-all of the service world," Raiff says, adding, "We've proven over 30 years that we can deliver far better service without selling you a fraction or selling you a five-year leased membership scheme. And you're calling a call center with a gazillion people in it, and you're just another number in another flight."

Raiff continues, "In our high-touch business, you're not obligated to anything ever. You can leave today. And that creates a level of customer care and customer service that is unparalleled by someone that's asking you to sign your life away for five years."

Raiff says PJS does all the things a good and experienced charter broker will do, including vetting operators and pilots, and ensuring the type of aircraft you want to fly in can safely land at the airport you want to go to. He calls safety "table stakes." On-demand charter also enables you to choose airplane types and configurations based on your mission, including specifying specific WiFi options that may not be guaranteed in a programmatic offering.

However, Raiff says the difference between the PJS private client experience and other on-demand brokers is the intense itinerary planning and flight monitoring that comes with each trip. He says PJS can channel decades of experience from its work with entertainers, sports teams, and political campaigns, combined with the eight-figure investment in AI and technology that is helping power its app.

For PJS, while technology automates the mundane, each flight by the private group is monitored by two dedicated employees who serve as lead blockers to get ahead of weather diversions, runway closures, customs office staffing shortages, last minute operational needs to switch FBOs, and the other variables that constantly pop up and turn what was going to be a perfect flight into one with preventable delays.

Milton Pedraza, CEO of the Luxury Institute, which helps luxury brands implement service delivery strategies, says that for Elevate Jet, it makes sense to both launch the app and double down on its private client business.

He says the assumption, held by many in the digital space, that the next generation wants to do everything online is incorrect.

Pedraza says, in fact, for luxury brands from Rolls-Royce Motor Cars to Zegna, it is the custom business, be it bespoke interiors or made-to-measure suits and shoes, that is the fastest growing segment of their businesses, with demand coming from all age groups. In travel, Pedraza notes, it is the same consumers who are flying privately powering the growth for travel agency groups like Virtuoso, where a new generation of travel advisors are using behind-the-scenes technology with personal relationships and product knowledge to run circles around booking websites.

Pedraza adds, "There’s a place for automated do-it-yourself in any category, but in any high-value, high-risk, high-emotion purchase, you are going to want a person."

Asked which side of Elevate’s business he would invest in if he could choose only one, Pedraza said, "I would invest in the private bank side, but in some cases, the same private bank client will use the app, and maybe that's how they will find out about the private client business."

From Raiff’s perspective, if Elevate Jet’s app becomes the entry point for high-spending clients to PJS, he's fine with that. Can Elevate Jet achieve household-name status? Without high-profile celebrity partnerships, an IPO, or big jet orders, a booking app, even if it works, may not be enough.