A superstar's road to Lolla is pretty unambiguous. Big bands have big followings. Lolla has a big space. Talent buyers and booking agents do what they do, and voila: Metallica is playing Grant Park for 100,000 screaming metalheads.

But it's not so cut an dry with a singer like Janelle Kroll, who plays Saturday at noon on the BMI stage—the same one Chance the Rapper and Lady Gaga have bulldozed in recent years. Since decamping for Brooklyn in 2013, the Chicago native and Northwestern alum has released a steady stream of dreamy art-pop singles, including a cover of Joni Mitchell's "Down to You" this week, produced by TYLERxCORDY—which is to say she's in the baby stages of a promising career.

To get a sense of how Lolla treats its rising artists, I met Kroll after a rehearsal in Wicker Park on Tuesday, where we talked timetables, comp tickets, and the festival's maligned radius clause. Below is an edited transcript of our conversation.

So how did you get on the bill?

Basically, BMI has the most incredible artist services.

Could you explain what BMI is?

It’s a performance rights organization. They help creators collect residuals, much like ASCAP or SESAC. When I first moved to New York, I played a show at Brooklyn Bowl, and a representative on their artist relations side was there. And he said "Hey, what’s your story?" He started setting me up on session work—just sitting down and making a song, trying out a bunch of new relationships, kind of like musical dating. So BMI from the start was very helpful in New York.

So you basically got old-school "discovered"?

Yeah, and [the representative] set up a couple introductions that were the gateway into this new moment in my creative journey.

How did you get the gig at Brooklyn Bowl?

It was actually a Northwestern alumni show. It was me and my friend Morgan Karr, who’s a badass. But that was a few years ago.

How did BMI get you from there to Lolla?

Well, I had a song on Defected Records that was getting a lot of airplay in the UK, and this woman Samantha Cox at BMI got more involved in what I’d been doing. And they curate a stage [at Lolla] every year. Then, in February, I put out a song, "Sunny Days" that had a lot of press, and with that Samantha pitched me to [Lolla organizer] C3.

So timetable-wise, you pitched them in February?

Early February I released the song, and I must’ve found out in March. I remember leaving a session in East Village with Tyler Cordy, and I get a phone call from Samantha, and she says, “You’ve been submitted to C3. That’s happening.” I had a nice little cry in that stairwell.

Did Lolla give you any guidelines as to the type of set to play—the set list or how to act or whether to play with a band?

No. I’m throwing in a ballad that they especially love [at BMI], but it’s free reign. I just want to make sure there’s movement. I have a lot of slow songs, but my project isn’t chamomile tea. Because it’s noon and it’s a festival date, I want to make sure some of my more rhythmic songs are in the set.

Are you going to play with a band?

Yes. I wanted to replicate what I’m doing in New York, so I have a keyboardist and a drummer and digital drumpads and a guitarist, and it also involves stems.

Did Lolla impose a radius clause?

Yeah, I knew there was a radius clause. I almost did a [local] performance with JBTV tomorrow, but I was only going to get in one rehearsal with my band, so I canceled the show. But [C3] approved it.

What does the clause look like? I’ve heard that artists can't play within 300 miles of Chicago for three months before Lolla and six months after it.

I don’t recall. The radius clause, from what I remember, wasn’t extreme. Geographically, New York is just a different territory, so it's just not an issue for me. I’m not in the middle of a tour. From what I understand, C3 can be very flexible.

You said that C3 approved the JBTV show before you canceled it. How did that process go?

I just shot a quick email to C3 and said, ‘Hey, I want to do this promotional show.' It was very easy.

Do you foresee the clause being an issue in the coming months, with Chicago being your hometown?

No, it really wasn’t prohibitive. But I do plan on coming back to do the JBTV performance, because you can invite 150 people and it’s free. Lollapalooza, by the time [the lineup] was announced, was already sold out, so my friends couldn’t get tickets.

Does Lolla let you bring anybody at all for free?

C3 gives you a small number of comps, and I was able to work a few extra thanks to BMI, but it’s barely anyone. But it’s OK. I’m doing a social media takeover this week with Rebecca Minkoff, so that should help [turnout]. And there aren’t that many artists playing early in the day, and a lot of industry comes out. So I’m not worried. It sucks that all my friends can’t be there, but there’ll be more.

Have you ever actually been to Lolla?

Two times. The first time was when Gaga played, in 2010. I was just in the very beginning stages of this journey, and I was like, "God, how on earth is this going to happen?" It’s an overwhelming feeling—like, fuck, there are so many hurdles.

How does it feel to go back as a performer?

It’s great. I’m overwhelmed with gratitude. It’s just one show, but being from Chicago, it’s the show. I mean, I’d sing in an elevator. But symbolically, it’s like, "I did it."

Do you have any expectations for the show?

I just plan on putting on a great set. I’m not expecting, "Oh, this means I’m gonna make X amount of dollars, I’m gonna be on tour with Jessie Ware." I just want to connect with people. And I can’t wait to roam around and see the shows.

Does C3 give you a weekend pass?

Yes, of course. Friday I’m gonna be chilling and rehearsing and sleeping early—which is hard for me, and also sucks because Paul McCartney is playing. Then I’ll just run around and hopefully connect with more artists, the music fam.

What are you most nervous about?

Let’s just hope it doesn’t thunderstorm.