For the past few months, things seem to have only been getting better for Sabrina Carpenter. Last summer, while opening on Taylor Swift’s Eras Tour, she began going viral for the city-specific outros she would tack on to the end of her song “Nonsense,” a true fan-driven hit that reached No. 56 on the Hot 100 and No. 10 on Pop Airplay. Next came “Feather,” off the deluxe edition of her Emails I Can’t Send album, which went even further, reaching No. 21 on the Hot 100 and becoming her first-ever Pop Airplay No. 1 earlier this year.

But that was just the beginning. “Espresso,” her single she released on top of her Coachella performance in April, exploded to No. 2 on the Hot 100 and No. 1 on the Global 200, cementing her as the pop superstar of the moment, crowned accordingly with a performance (and skit appearance) on Saturday Night Live. But her latest single, “Please Please Please,” then went even further — after debuting at No. 2 on the Hot 100 and giving her the top two songs on the Global 200, “Please Please Please” then ascended to the top of both charts, giving Carpenter her first-ever Hot 100 No. 1 and the distinction of replacing herself atop the global charts.

The momentum has been dizzying — with every level conquered, another fell right after. Or, as Island Records vp of A&R Jackie Winkler puts it, “‘Nonsense’ walked so ‘Feather’ could jog, then ‘Espresso’ ran so that ‘Please Please Please’ could start a stampede.” And the success earns Winkler, who originally signed Carpenter to Island and has worked with her ever since, the title of Billboard’s Executive of the Week.

Here, Winkler talks about the building success of each of these songs, Carpenter’s evolution as a songwriter, the way that A&R has evolved over the years — and what will come next. “I think this album is going to blow people away,” Winkler says of Carpenter’s forthcoming Short N’ Sweet, due out in August. “If you like ‘Please Please Please’ and ‘Espresso,’ just wait for what’s in store.”

This week, Sabrina Carpenter’s “Please Please Please” reached No. 1 on the Hot 100, her first-ever song to top the chart. What key decision did you make to help make that happen?

Sabrina and Jack Antonoff had known each other personally for some time, so it was a natural progression for them to eventually work together. Given the chemistry that Sabrina and Amy Allen had already built, putting the three of them together felt like the perfect musical combination to undoubtedly yield something exceptional. It’s also fun to share the success of this song with David Gray and Jenn Knoepfle at UMPG who were instrumental in connecting the dots.

“Please Please Please” also hit No. 1 on the Global 200, replacing “Espresso,” which was No. 1 last week. Why do you think these songs are resonating, and working so well, around the globe?

To put it simply, the two songs speak for themselves. The first time I heard “Please Please Please” and “Espresso,” both sounded like hit records to me. The extraordinary nuances of Sabrina’s vocal delivery and quick-witted lyrics, combined with Jack Antonoff and Julian Bunetta’s brilliant productions, all play an essential role in what makes these songs so infectious and undeniable. They are especially bold, and nobody could pull them off as fearlessly and authentically as Sabrina.

Since last year, Sabrina has been on an increasingly-ascendant run up the charts, from “Nonsense” to “Feather” to “Espresso” and “Please Please Please.” How have you worked with her to help her develop her sound in the past year to reach this level?

It really feels like all four songs came at the perfect times in her career. “Nonsense” walked so “Feather” could jog, then “Espresso” ran so that “Please Please Please” could start a stampede. At the core, the music Sabrina makes is perfectly reflective of who she is as a person, and all the quirks and character are what give her such a strong musical identity. Writing with her friends has always felt like the most effortless way to allow her to be herself, so protecting that process at all costs will remain a vital part of her ever-evolving sound.

You originally signed Sabrina to Island several years ago. How have you seen her develop as a songwriter and as an artist since then?

From day one, Sabrina’s superpower has always been knowing exactly who she is and the type of musical collaborators she’s wanted to work with. I’ve witnessed her develop into an extraordinary songwriter who has not only coined entirely new phrases, but also infiltrated popular culture around the world with her lyricism alone. One of the most rewarding parts about seeing her succeed is that none of this has happened by skipping steps or catching a lucky break. It is all owed to her remarkable talent, the music itself and the relentless detail put into every aspect of her creative campaign. [Island co-CEOs] Justin Eshak and Imran Majid are ambitious leaders who strongly encourage our artists and our Island Records staff to take risks musically and strategically, which has made this journey even more gratifying as we continue to charge forward with no limitations.

With such a string of successful singles, how does that influence your approach to her upcoming album?

I think this album is going to blow people away. If you like “Please Please Please” and “Espresso,” just wait for what’s in store. Every ounce of the album oozes with Sabrina’s personality — funny, sincere, cheeky and intelligent, but above all, it’s honest. There isn’t a single song on the album that one could mistake for another artist, which is by far my favorite part. 

How has A&R changed over the course of your career, and how has technology changed the role?

Technology continues to be a valuable tool for us to perform our jobs more efficiently. Since the start of my career, our access to information, data and even resources used to break artists have multiplied; however, my approach to signings, choosing singles and pairing creatives has never wavered from following my gut instinct. What will remain constant in A&R is the importance of maintaining genuine relationships, remaining selective and staying true to finding artists with longevity, a point of view and an unparalleled vision.