The tricky part about being Cadillac is that it’s awfully easy to get tripped up in a 114-year-old history of glamour, glitz, and glorious fins.

After World War II, Americans began to drive in droves, and Cadillac became a metaphor for the best of the best. Even the names of its finest saloons — El Dorado, Coupe de Ville — had a certain flair. Cadillac was larger in stature than the luxury marques of the time: the clients of fitness guru Joseph Pilates named the popular six-foot tall workout apparatus after the finest marque of the era. But as the General Motors business model refocused on the mass market in the 1970s and '80s, the exclusivity and joie de vivre associated with the Cadillac crest seeped away. Eventually, the brand’s models became shadows of their former selves, better suited for the senior citizen set and nostalgic collectors. Cadillac had a brief resurgence in the early aughts as rappers, sports stars, and actors embraced its chrome-clad Escalade — alongside Gucci and Louis Vuitton — as a representation of entrepreneurial luxury. But then came a recession, rebates, and retro fatigue.

What Cadillac was sorely missing was a decent, lean-and-mean sedan that could square off with the minimalist German makes. When the second generation CTS came along in 2008, Cadillac finally proved that it could make a modern car, free from the burdens of its heritage. And in the intervening years, the brand has muscled its way back into luxury buyers’ minds with several handsome products that boast surprisingly competitive performance figures. (The current CTS-V and the ATS-V have further boosted the brand’s track cred.) And recently I spent time in the refined CT6 flagship that produces a formidable 404 horsepower from a twin-turbo V-6 engine and will be sold as a plug-in hybrid next year. The first of four upcoming Cadillac crossovers, the XT5, goes on sale this summer, setting the brand up for a bigger footprint in the auto industry’s most profitable segment.

Enter Johan de Nysschen, Cadillac’s president, the South African native who has been charged with rebuilding the marque from the ground up. A Detroit outsider, de Nysschen looks at the world from an international perspective: he is credited with putting Audi in the same playing field as BMW and Mercedes-Benz, no small feat. Two years ago, he joined Cadillac after a short time at the helm of Infiniti, leading a move from Detroit to New York City’s high-rent SoHo district in an effort to soak in some of the Big Apple’s mojo.

Johan de Nysschen stands in Cadillac's New York City offices.

His team of 110 New York City-based employees are reimagining what a luxury car experience means, using the physical distance from GM’s Detroit headquarters to fashion the brand more like a startup than a stodgy, century-old fixture of the Motor City. The finished offices, designed by famed architecture firm Gensler, feel contemporary, clean, and airy, overlooking the Hudson River. Images and references to chic, mid-century, modern Cadillac — the brand’s heyday — are used in subtle, almost tentative ways. Conference rooms are named for concept cars. Pucci coffee table books are displayed in the lobby.

I met with de Nysschen at the office on a sunny Friday in June. Tall, lean, and serious, he has the intimidating presence of a distinguished economics professor. "I’m no artist, but I’m going to draw you a picture. I speak better in pictures. Imagine the car market is shaped like a triangle," he says, taking out a marker to emphasize his point with his office windows as a whiteboard. "I want to use today to explain the context of what I’m doing. It’s all part of the grand plan." Over the course of the hour, de Nysschen made his case for Cadillac’s resurgence. At first he paced the room, scoffing at critics who have questioned Cadillac’s current sales numbers. He makes it clear that he’s playing the long game, as long as GM has the patience.

The next stage in transforming Cadillac is to bring its 925 dealers up to snuff. That’s where the Cadillac House comes into play, a chic public space where anyone can drop by and steep in the brand’s past, present, and future. Each detail of the facility has been carefully considered — it sells Joe Coffee (a local favorite), offers free Wi-Fi, stages art installations curated by Visionaire and fashion collections selected by the Council of Fashion Designers of America; at its June opening, it hosted a block party bash featuring a short set by My Morning Jacket. The Cadillac House has a few cars on view, but it’s not a car dealership. Discreet product specialists are trained to answer questions about features on new models like the CT6.

You can think of Cadillac House as the base camp for the brand’s vision. "Our office, the Cadillac House, this is what our dealer experience should be like. Our focus here must be on increasing the overall quality of the business. It must be about increasing transaction prices. It must be about brand positioning and upgrading quality of the dealer and doing so in a way that we continue to build the relationship between Cadillac the manufacturer and our dealer network. We have to navigate a very difficult path," de Nysschen tells me. He references a new program to increase dealer rewards. "It’s really those small dealers that we want to turn into powerhouses. We want to create a boutique experience, separate from the rest of the GM brand, and we want to help our dealers."

But US dealers are only one part of the sales puzzle. Cadillac, like most luxury brands, is still betting heavily on China, where it is building a sales experience from the ground up. Cadillac recently opened its $1.3 billion-dollar factory outside of Shanghai.

But in a future where people might not visit car dealerships to shop for cars, de Nysschens is savvy enough to test the waters with technology-driven models. "Five short years ago, customers were visiting 2.6 stores before making a purchase. Today it’s 1.2. Why? Because they are doing more of their research online. Basically the purpose for going to the dealership is to formalize the transaction, but also you have to reevaluate where and how we do business with a customer, unless we want to become completely disrupted. If so much of the purchasing of physical goods is happening online why should our industry be totally immune to that?" His descriptions give way to upcoming plans, like a virtual reality showroom. "All of the technology is packed in there and we go and visit the customer and we can give this fully immersive virtual reality experience of the vehicle showroom, of the technology of the car." He says they have had a prototype demonstration in the office and are only months from launching.

Cadillac is also likely to add its own twist to Maven, GM’s car-sharing program that’s in the process of getting up and running. It has to be able to compete with competitors such as BMW’s ReachNow, which offers upmarket vehicles from BMW and Mini. de Nysschen describes a white-glove car-sharing service. He explains how Cadillac customers could use the Maven app to request an Escalade one day and then opt for a CTS-V the next. The person who delivers or picks up the car to the customer would alleviate the need for parking, gassing or charging up, and visits to the car wash.

For now, he says most people drive the cars they buy from car dealers, particularly those who live outside of big cities — but that Cadillac can play in the mobility space, too. "We should look at vehicle ownership as a continuum at two bookends," he says. "One bookend is today’s conventional ownership where you buy the car, then you have leasing, and then you can have a car-sharing service like Zipcar, you can have ride-sharing, and you can have individual ownership per ride. By that definition, I don’t want it to be just a ubiquitous Uber ride, I want it to be a Cadillac ownership experience per individual journey."

Speaking of Uber, de Nysschen is concerned that the growing ride-sharing industry could decimate automakers if the industry doesn’t respond. "Uber doesn’t really care what kind of brand of vehicle it offers to customers at this stage. Given that Uber and Lyft are the two dominating ride-sharing services, they are not yet at the point where they can adequately differentiate themselves from each other by saying I will give you an immersive brand experience." It’s no coincidence that his warning lines up with GM’s aggressive moves into the space, including a $500 million investment in Lyft.

I asked him about traveling to places like Los Angeles, where Uber is cheaper and more convenient than renting a car. He thinks that while some people only care about the functional aspects of transportation, others will seek out the high-end luxury treatment that Cadillac could offer. "For me, I absolutely will not be moved around in an Uber. I don’t feel like being moved around by some Hyundai Sante Fe. It’s not how I roll, so I keep the car. I’m thinking if there was a Lyft service — because we have a strategic interest with them — that offered me the guarantee it would be a Cadillac, I would have an entirely different approach. I’ve got to believe there are others like me, too."

He’s also enthusiastic about vehicle-to-vehicle (V2V) communication, which makes its industry debut in the 2017 CTS this fall. "We could argue that no one’s going to line up around the block, but if you always want to wait for commercial reason, you’ll be lost. Someone has to be first."

It’s only been a year since Cadillac moved away from home, but maybe a little bit of that New York urgency has trickled into its veins already.

Portrait photo of Johan de Nysschen by James Bareham

Photographs of Cadillac House by Amelia Holowaty Krales