Join the ride: Jenn Sherman recalls how she became Peloton's first-ever instructor

There's a seven-year-old email that Jenn Sherman keeps on her phone, one she sent to her future employer requesting — demanding, actually — a job.

"I didn't even know if they were hiring, but in the subject line, I said, 'You need to hire me,'" she says. "I thought, 'I'll be ballsy, I'll go for it.'"

It was a fateful move. Two days after hitting send, Sherman heard back from the email's recipient, John Foley, founder and CEO of then-startup Peloton.

"He said, 'There's something about your email and the way you wrote it, and I got a great feeling from you,'" she says. Not only did Sherman's email lead to her being hired as the exercise and media company's first cycling instructor, but Foley has kept it on his phone, too.

"It's infamous," says Sherman. "It comes up over drinks at our Christmas party every year."

Jenn Sherman has been a Peloton instructor since day one.
Jenn Sherman has been a Peloton instructor since day one.

Sherman, 52 is known for her salty expressions of enthusiasm — her fans praise her high energy, positivity and warmth. Every week, Sherman attracts thousands of subscribing Peloton members who ride along with her on the company's stationary bicycles, either during live classes streamed from the company's NYC studios, or recordings of those rides available in its vast On Demand library.

Through the software on their bikes and digital apps, cyclists in their homes might be part of a virtual gathering that includes LeBron James, the Obamas, President Joe Biden or radio personality Howard Stern, who talks about Sherman's classes on the air. Members also organize "tribes," groups and teams who can work out together and share information about their favorite instructors; Sherman's JSS Tribe on Facebook has more than 9,500 members.

With so many avid followers, Sherman's career is even more impressive considering it began less than a decade ago.

Obsessed with exercise

At Fort Lee High School in New Jersey, Sherman "played 0.0 sports," she says. "I didn't even have the courage to try out for cheerleading. But working out and getting sweaty has always been a huge part of my life. When step and aerobics classes were all the rage, that's what I did. It's in my personality to become obsessed." When she was about 40, she says, a friend took her to an indoor cycling class, and an enduring obsession took hold. "It filled me up and gave me so much joy," she recalls.

"I was a stay-at-home mom, but when my kids started growing up, I had time on my hands, and I couldn't just sit around and have lunch with friends," says Sherman. So she became a certified spin instructor.

Soon, she was teaching up to seven days a week. Her classes were packed, a situation Shirley Bitton, an Englewood mother of five and administrator of the JSS Tribe Facebook group, remembers well. "I saw people standing in line at the gym for 20-30 minutes every Tuesday, and I'd think 'What are they giving way?'" she says. "A friend said, 'Oh, that's Jenn Sherman's spin class.'"

Demarest, NJ, Jenn Sherman has been a Peloton instructor since day one.
Demarest, NJ, Jenn Sherman has been a Peloton instructor since day one.

By 2013, Sherman was ready for a bigger challenge. Along with a business partner, she had secured a location and was ready to sign a lease to open her own studio. But then she happened upon an article about Peloton.

"It had a picture of a spin bike with a screen attached to the handlebars," she says. "The writeup explained how this company was bringing boutique indoor cycling classes like the ones I was teaching into customer's homes, so you didn't have to fight crowds or get on a waitlist, the way people did to get into my class."

This early iteration of the Peloton bike wasn't the one that ended up being sold to customers, but the concept sold Sherman on what her next move should be. After firing off her email to the address listed at the bottom of the article, she met John Foley in Manhattan and visited the startup's office on 23rd Street. "There were seven geniuses writing code, figuring out how to make something of this grand idea," she says.

"(Foley) looked at me that day and said, 'Joining a startup can be intense, and things are going to move at lightning speeds. Do you want to hop on and join the ride?'" Sherman returned home and told her partner that regretfully, she couldn't open a studio with her. (Today, Sherman says, the woman is a Peloton owner of seven years.)

No one owned a Peloton bike in the fall of 2013, which gave Sherman time to rehearsein the office, in an area sectioned off with a black velvet rope where a bike was set up in front of a camera on a tripod. She says she felt sick the first time she held a live class. By the time the studio was set to open in spring of 2014, there were seven to 10 instructors scheduled to teach on different days. Cyclists could spin along from home or in person at the studio.

"A bunch of the team members are amazing fitness instructors and do have a background in film, TV, dance and theater," says Sherman. "But I was a mom of two young kids who knew how to go to the carpool line. I couldn't bring that to the table. It took a long time to get comfortable when that red light goes on. But a benefit of being one of the earliest instructors was being able to work it out with nobody watching. The day I had 50 live riders, I thought 'Yes!'"

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Reaching a global audience

LAS VEGAS, NV - JANUARY 11:  Maggie Lu is reflected in a touch screen as she demonstrates how to select a class on a Peloton Tread treadmill during CES 2018 at the Las Vegas Convention Center on January 11, 2018 in Las Vegas, Nevada. The USD 3,995 workout machine is expected to be available later this year and features a 32-inch touch screen that connects users to instructors giving live or on-demand fitness classes. CES, the world's largest annual consumer technology trade show, runs through January 12 and features about 3,900 exhibitors showing off their latest products and services to more than 170,000 attendees.  (Photo by Ethan Miller/Getty Images)

On a recent Sunday, Sherman had close to 6,000 riders joining her class. She is one of 33 Peloton instructors leading 3.6 million members in the U.S., United Kingdom and Germany who cycle, work out on Peloton's treadmill or practice yoga. Sherman's classes range in length and ambitiousness, from 10-minute low-impact rides to 60-minute "epic singalongs." But they all feature the signature "[expletive] amazing playlists" for which she is known.

"Playlists take you on a journey," she says. "There are powerful moments when you're asking riders to do something uncomfortable like a big push, and the way you time your music is key to building an amazing class." A typical playlist might include live versions of well-known songs that are easy to sing along to, such as "Stay" (Dave Matthews Band), "Dream On" (Aerosmith), "Tenth Avenue Freeze-Out" (Bruce Springsteen) and "Piano Man" (Billy Joel).

When COVID-19 arrived, Peloton instructors streamed classes from their homes, but they have since returned to record instruction live in the studio, without participants surrounding them. It's times like these, her followers on social media tell her, when being able to come together as a group is most appreciated.

JayVee Nava, Peloton's VP of community engagement, who has known Sherman since joining the company in early 2014, was touched by the virtual Live from Home class Sherman held during the company's annual three-day Homecoming celebration earlier this year.

Demarest, NJ, Jenn Sherman has been a Peloton instructor since day one.Sherman at annual Peloton Homecoming in 2019 with other Peloton members outside of the former Peloton Studio in NYC
Demarest, NJ, Jenn Sherman has been a Peloton instructor since day one.Sherman at annual Peloton Homecoming in 2019 with other Peloton members outside of the former Peloton Studio in NYC

"She knew how much this weekend meant for our members and for our team, and she gave me a shout out during class," says Nava. "The moment she gave me a shout out, I immediately received high fives from fellow members on the Leaderboard (metrics displayed on the screen)."

Sherman says she is inundated with hundreds of messages daily, especially on her Instagram account, @Pelotonjenn. "I'm up at night reading them, and they bring me to tears on a daily basis," she says. "People are pouring their hearts out saying 'I don't know if I could have gotten through this without Peloton.'"

She knows exactly what they're talking about. "The last year, with the kids homeschooled, my son's college life a [expletive]show, and the stresses of working at home the same time as my husband, I was so tense except when I was (on my Peloton)," she says. "Peloton was my safe space during all this. The community is what sets us apart from every other thing out there."

Shirley Bitton, who has been cycling with Sherman for 11 years now, agrees, especially when it comes to how Sherman makes her cyclists feel. "People who ride with her talk about her having that personal relationship with you through the screen," she says. "Riding with her feels like I'm having a cup of coffee with her while getting a workout."

Tips for late beginners

"When you're starting out with a new health and wellness program, everyone needs to get motivated," says Sherman. "Movement will be key to your joy. There are so many mental and physical benefits from getting sweaty and raising endorphin and serotonin levels." To stay with the program, she advises:

  • Carve out time in your schedule. "There's 24 hours a day, but there's never enough time. But you need to make it a priority."

  • Start slow. "Set small, achievable goals," she says. "Don't reach for the stars on Day One."

  • Don't worry about the length of time. "Twenty minutes is better than nothing."

  • Be consistent. "You'll get stronger, and it gets easier."

  • Reward yourself. "When you achieve a goal, tell yourself 'I just did that!' If you achieve bigger goals, get a new pair of running shoes or a massage."

This article originally appeared on Peloton instructor Jenn Sherman on how it all began, her playlists