On This Indianapolis 500 Team, the Boss Is a Woman. So Is the Driver. And the Mechanic. And the Engineer. – The Wall Street Journal

“I was like, ‘Yeah, that’s fine,’ Paretta recalls. “In my head, I’m like, ‘Oh, my God.’ ”

At the time, Paretta was working her way up in the auto business. Penske, meanwhile, was already a legend, a former race car driver turned entrepreneur known succinctly as “The Captain,” with vast influence across the industry and sport.

Still, when the Captain joined the call, Paretta held her ground. 

“We were back and forth for like 10 minutes,” she recalls. She had her opinion; Penske had his. After she got off the phone, “I looked this area manager right in the eye. I go, ‘I just raised my voice to Roger Penske.’ He looked at me, smiled, and said, ‘He’ll respect you for it.’”

“To me, she was doing her job, and I was doing mine,” Roger Penske tells me, 14 years later. “We obviously ended up as friends.”

This is true. Not long after, Penske and Paretta would meet for the first time in person at the Detroit Auto Show, where the mogul shook her hand and asked her to join him for a walk around the event. Paretta would continue to rise up the ranks in the auto business and in motor sports with Fiat Chrysler America. Roger Penske would keep on being, well, Roger Penske. This weekend, the two friends, now 47 and 84, respectively, are combining forces for an ambitious endeavor:

A women’s team at the Indianapolis 500. 

On Sunday, May 30, at Indianapolis Motor Speedway, the veteran Swiss driver Simona De Silvestro will drive a car for a Penske-backed Paretta Autosport team that includes a woman not only behind the wheel, but throughout the team at key positions, including spotters, mechanics, engineers and a pit crew “going over the wall” at the Brickyard. 

Says Penske: “It’s very exciting to me.” 

The team is part of a “Racing for Equality and Change Initiative” launched by IndyCar early last summer. And while Paretta’s team, which does have some male personnel on its roster, is already getting a lot of attention, its focus is familiar to anyone who’s competed in the business.

“We’re all working so hard…but everybody wants to win the thing,” Paretta says. “As much as we politely say, ‘Oh, it’s just an honor to be nominated.’ No! You want to win.”

De Silvestro and the Paretta Autosport car will have their work cut out for them. The team edged into the race with a final day qualification, and they will start Sunday’s 500 in the last row, in a group with 2018 winner and Team Penske driver Will Power. They’re not the favorites by any stretch, but they’re eager for a fast, smooth debut.

“This will be good for the sport,” says Penske. 

These days, Penske doesn’t merely simply compete at the Indianapolis 500—he owns the place. Penske Entertainment Corporation purchased the Speedway grounds and IndyCar racing from the Hulman family in 2019. The pandemic wound up disrupting Penske’s initial IndyCar season, as the 500 was moved until late August, and fans were barred from attending. This Sunday, however, 135,000 are expected—a fraction of the 350,000 or so the Speedway can hold, but a major upgrade from a year ago. 

“We’re focused in 2021 on fan experience,” Penske says. “To me, this is the most important thing. We want people to come here and have fun. We want young people to come.”

The Paretta Autosport Team is not the only outfit coming out of the “Race for Equality and Change,” which Penske’s IndyCar announced last year, and seeks to develop auto sports talent from underrepresented communities. Penske is also aligned with Force Indy, a Black team owned by longtime racing exec Rod Reid which is currently competing at the sport’s developmental USF2000 level with driver Myles Rowe. 

“We want to win,” Reid says, echoing Paretta’s competitiveness. “Some people look at us and say, ‘Oh, just the fact that there are black guys and girls on the team, that’s the goal,’ No. That’s part of the strategy. The goal is to win races.” The Force Indy car bears the No. 99, a homage to the pioneering Black auto racing champion Dewey “Rajo Jack” Gatson.

As for Paretta, Sunday’s start represents a major personal achievement. The Connecticut native, who grew up reading car magazines as a child, came close to getting a women’s Indy 500 team off the ground in 2016, one reason why Penske felt confident backing her for 2021. This year hasn’t been easy, however, as Covid-19 restrictions and travel issues complicated matters. The 32-year-old De Silvestro, who finished 14th at the Indianapolis 500 in 2010, winning the race’s “Rookie of the Year,” lives overseas, and didn’t get to meet Paretta and the rest of the team in person until this spring. 

Still, Paretta is feeling upbeat about her operation: the car, the driver, the team, her friend Roger, and the message. 

“It’s just giving opportunity,” Paretta says. “Obviously, the person has to have the résumé, but…if the attitude and the work ethic is there, and the aptitude, sometimes it’s OK to take a chance on somebody.

“They can surprise you.”

Write to Jason Gay at Jason.Gay@wsj.com