8 Hardest Peloton Instructors To Speed Up Your Productivity

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BY James Roland
Updated on 07/07/2022

Beginner classes are perfect options for first-timers. However, once the current lessons are too simple for you and you want to maximize your productivity, challenge yourself with advanced classes.

It may be hard when first moving to a higher level. Yet, our list of the 8 hardest Peloton instructors will help simplify your rough journey. So what are you waiting for? Let’s check it out and find your favorite trainer!

When Are You Ready For Advanced Peloton Classes?

Peloton offers classes on three levels: Beginner, Intermediate, and Advanced. It’s advisable to reach the final one after the first two have become a breeze for you.

  • Beginner

This level is for those who just have started working out. Try to experiment with the classes in a few weeks by joining short classes and basic exercises for newbies. They help your body familiarize yourself with the training session without causing pain.

  • Intermediate

Work your way up to the Intermediate category after feeling comfortable with the Beginner classes. You should stick to this level for several months. The Intermediate lessons will help improve your strength and endurance significantly.

  • Advanced 

This level is suitable for people who understand the exercises and know what their bodies need. Yet, they should still start with short classes first and push themselves later if they are ready.



Hardest Peloton Instructors For Cycling

You can’t choose the difficulty level for Peloton cycling classes. However, the rides come with many exercises, some of which are really hard for beginners. Hence, we name Kendall Toole and Olivia Amato because they offer many challenging classes.

1. Kendall Toole

Who is Kendall Toole?

Kendal Toole was born in Texas, the United States, in 1993. There isn’t much information about her family, but the instructor’s always happy when talking about her parents.

Kendal has experienced different jobs. Before becoming a part of Peloton, she was an actress and joined several projects, like Little Canyon (2008), Arcadia (2012), and Frat House Musical (2012). She is also the founder and co-president of Fervor Entertainment.

Fitness is also her interest. You may find her on Instagram as a fitness influencer. As a Peloton cycling instructor, Toole has inspired many people with a healthy lifestyle.



Difficulty level: 8.28

Class overview (updated in 2022)

There are 528 cycling classes by Kendall Toole available. So feel free to aim for the best one after checking all the options.

  • Class type: Warm Up/Cool Down, Beginner, Low Impact, Music, Theme, Intervals, Climb, and Power Zone
  • Class length: 5 to 60 minutes
  • Class music: Alternative, Classic Rock, Electronic, Country, Latin, Pop, Hip Hop, Rock, and R&B

Why should you choose?

If you choose Kendall’s classes, you will have these benefits:

  • There are many HIIT rides to select from. These exercises will be perfect choices for strengthening your muscles.
  • Her humorous teaching style makes the atmosphere more comfortable, although the lessons are hard.
  • The trainer is so dedicated to every minute she’s on the camera. She even tries to mix her outfit to fit the vibe of her lesson.


2. Olivia Amato

Who is Olivia Amato?

Olivia is a cycling, running, and strength instructor at Peloton. She was born in New York City, the United States, in 1991.

After studying Business and Finance, Amato took her first job in the Sales and Trading division on Wall Street. However, she decided to change her job because of her passion for fitness.

Rebecca Kennedy, a Peloton instructor, discovered Olivia’s talents after observing her class at a studio in NYC. Then, Rebecca invited her to join an audition.



Difficulty level: 8.35

Class overview (updated in 2022)

Olive Amato is also a good instructor for beginners in her cardio classes. However, her cycling lessons are much harder, requiring a higher skill set.

There are 358 cycling classes of this trainer to choose from. You can pick your favorite by filtering the type, length, and music.

  • Class type: Warm Up/Cool Down, Beginner, Low Impact, Music, Theme, Intervals, Climb, Power Zone, and Peloton Studio Original
  • Class length: 5 to 45 minutes
  • Class music: Classic Rock, Electronic, Country, Latin, Pop, Hip Hop, and Rock

Why should you choose?

Olivia Amato is famous among Peloton users who look for advanced classes because:

  • Many of her classes have a difficulty level above 8.0. The most popular ones are Power Zone lessons.
  • You can try intense exercises with little rest in the middle.
  • The trainer will inspire you with the spirit of “Never Give Up” regardless of how hard the workouts are.


Hardest Peloton Instructors For Running

Although running sounds more difficult than cycling, it has less complicated lessons. The hardest Peloton running instructors offer difficulty levels around 7.1 to 7.1, which are lower than cycling instructors.

We highly recommend Jess Sims and Becs Gentry if you want to improve your running skills.

3. Jess Sims

Who is Jess Sims?

Born in the USA in 1990, Jess Sims was an energetic girl during her early life. She liked to play soccer, lacrosse, and basketball. However, unlike her active personality, Jess became a kindergarten teacher after graduation.

As you can guess, Jess Sims didn’t follow this career for too long. She returned to her fitness passion by becoming a HIIT and boxing instructor. 

Luckily, Rebecca Kennedy, one of her boxing students, invited Jess to Peloton in 2018. So, now, Jess Sims is a running, walking, Bootcamp, strength, and stretching trainer on this platform.



Difficulty level: 7.2

Class overview (updated in 2022)

Jess Sims has 167 running classes. You can choose the advanced-level classes and then select the class length and music.

  • Class type: Warm Up/Cool Down, Running Skills, Intervals, Endurance, Speed, Music, Theme, and Heart Rate Zone
  • Class length: 5 to 60 minutes
  • Class music: Electronic, Country, Latin, Pop, Hip Hop, and R&B

Why should you choose?

If you need an instructor to accompany your challenging journey, Jess Sims will be who you are looking for. By joining her classes, you will have some benefits:

  • The “glazed donut” warm-ups keep you on your toes.
  • Her interactive teaching style will encourage you to follow her speed.
  • Interval Runs can help you improve your strength and endurance considerably.


4. Becs Gentry

Who is Becs Gentry?

Becs Gentry was born in England in 1986. Gentry was an active and professional runner. You will spend hours checking for her running career achievements, and attending the Tokyo Olympics 2021 is the most outstanding one.

Before joining the Peloton community, Becs Gentry was an office worker. However, this job didn’t suit her energetic personality. So, she quit the office career to follow a marathon journey and became a tread and strength Peloton instructor. 



Difficulty level: 7.1

Class overview (updated in 2022)

Becs Gentry has 533 running classes. You can choose the Heart Rate Zone lessons to improve your skills.

  • Class type: Running Skills, Warm Up/Cool Down, Theme, Music, Endurance, Speed, Intervals, and Heart Rate Zone
  • Class length: 5 to 60 minutes
  • Class music: Alternative, Country, Electronic, Hip Hop, Latin, Pop, R&B, and Rock

Why should you choose?

Becs Gentry is one of the most famous tread Peloton instructors for advanced classes because:

  • This professional runner has a high requirement for her students to speed up their progress.
  • Her unlimited energy will urge you to move forward.
  • Although the lessons are difficult, Becs Gentry knows how to motivate you by playing a perfect list for the atmosphere.  


Hardest Peloton Instructors For Yoga

Yoga isn’t as intense as running or cycling. As a result, it comes with a lower difficulty level, and even the hardest instructors have a rate around 6.5. However, you need to work a lot on your flexibility. If you find it too hard, Ross Rayburn and Anna Greenberg can give you a lot of help.

1. Ross Rayburn

Who is Ross Rayburn?

We can’t find Ross Rayburn’s personal information on the internet. However, you may have heard his name somewhere since he’s one of the most famous yoga instructors at Peloton. 

Ross Rayburn has experienced a severe injury. Then, he discovered that yoga could help with his healing and transformative properties. 

Ross has practiced yoga since 1997 and became a yoga trainer in 2003. He visited more than 30 countries to deliver lessons and motivate people to try this practice.



Difficulty level: 6.5

Class overview (updated in 2022)

Ross Rayburn has 643 yoga classes. His Restoration lessons are the best. You can also opt for other options as follows:

  • Class type: Flow, Focus Flow, Slow Flow, Restoration, Theme, Yoga Anywhere, Yoga Basics, and Beyond the Pose
  • Class length: 5 to 75 minutes
  • Class music: Alternative, Classic Rock, Electronic, Country, Latin, Pop, Hip Hop, Rock, and R&B

Why should you choose?

According to Peloton members, Ross Rayburn is the best choice for intermediate and advanced yoga classes because:

  • The instructor has been working in this category for nearly 20 years. His experience is the most impressive factor to consider.
  • His sarcastic personality makes the lessons interesting.
  • Although the classes are difficult, Ross doesn’t intimidate his students but gives them alternatives instead.


2. Anna Greenberg

Who is Anna Greenberg?

Anna Greenberg is an American yoga trainer at Peloton. She doesn’t mention her age, but we can guess she may be in their thirties.

During Greenberg’s teenage years, she suffered greatly from her toxic relationships and friends. Thankfully, her mother, a yoga teacher, helped her overcome this terrible period.

Anna Greenberg chose yoga as a way to heal others’ mental and physical health. With her 10-year experience in yoga, this instructor will give great help to exercisers from all levels.



Difficulty level: 6.5

Class overview (updated in 2022)

Anna Greenberg teaches many yoga classes. You can check their type, length, and music to opt for the most suitable choices among 686 yoga classes delivered by this American trainer.

  • Class type: Flow, Focus Flow, Slow Flow, Restoration, Theme, Yoga Anywhere, Yoga Basics, Family & Pre/Postnatal, and Beyond the Pose
  • Class length: 5 to 75 minutes
  • Class music: Alternative, Classic Rock, Electronic, Latin, Pop, Hip Hop, Rock, Indie, and R&B

Why should you choose?

Anna Greenberg will be a good choice if you look for advanced yoga classes because:

  • You can find many intermediate and advanced lessons in her library.
  • After working in yoga for ten years, the instructor knows how to lead your training sessions on the right path.
  • The instructor is excellent at helping you find space and stability in your mind and body. 


Hardest Peloton Instructors For Strength

Strength classes are the second hardest after cycling. The best choices for you in this category will be Tunde Oyeneyin and Rebecca Kennedy.

1. Tunde Oyeneyin

Who is Tunde Oyeneyin?

Tunde Oyeneyin is in her mid-thirties. She grew up in Texas with her parents.

Looking at her right now, you will be surprised to know that the trainer used to suffer from bullying because of her excess body weight. It even made her lose her confidence.

When Tunde couldn’t bear all the criticism, she decided to register for a gym membership and took her first step in the fitness world. She also attended aerobics classes and succeeded in losing weight.

Now, Tunde is a Peloton cycling and strength instructor. She takes her mission of inspiring people to work out seriously.



Difficulty level: 7.4

Class overview (updated in 2022)

Although cycling is her primary lesson (with 507 classes), some Peloton users first think of her name when choosing strength courses. With 24 strength classes, Tunde can also help with your goal.

  • Class type: Arms & Light Weights
  • Class length: 10 minutes
  • Class music: Electronic, Pop, Hip Hop, and R&B

Why should you choose?

Tunde Oyeneyin is one of the fiercest Peloton instructors. Even so, her classes are worth trying because:

  • The trainer can push you to break your limit. 
  • Many of her classes have a high difficulty level, around 8.1.
  • Tunde is also in charge of beginner classes, so she knows how to balance the intense degree of her exercises to fit all students.


2. Rebecca Kennedy

Who is Rebecca Kennedy?

Rebecca Kennedy is one of the most famous Peloton instructors. She has also helped Peloton invite many talented trainers to join the group as her position is Director of the Peloton Fitness Program. 

Rebecca is from America. The 27-year-old lady has gained many achievements in her career. For example, she’s an AFFA and NASM certified trainer. She also works with Nike, Under Armour, and Reebok as a model. You can also easily find her in Fitness, Self and Health, and Runners Worlds magazine.



Difficulty level: 7.7

Class overview (updated in 2022)

Rebecca Kennedy has 386 strength classes. Your options include:

  • Class type: Warm Up, Bodyweight, Full Body, Core, Upper Body, Lower Body, Strength for Runners, and Pilates
  • Class length: 5 to 45 minutes
  • Class music: Alternative, Electronic, Latin, Pop, Hip Hop, Rock, and R&B

Why should you choose?

Aside from her fame, you will find her classes interesting and beneficial for these reasons:

  • The instructor specializes in body weight workouts and will bring out the best of it in you.
  • The frequent use of animal movement style eliminates the need for weights.
  • Rebecca aims to improve your mental and physical health. 


Benefits Of Hard Peloton Classes

Many people set their goals of achieving advanced Peloton classes for the following reasons:

  • There are many HIIT (High-Intensity Interval Training) classes at this level. These exercises do an excellent job of lowering your blood pressure and improving your endurance.
  • Bootcamp rides in this category will help build muscle and burn fat incredibly. 
  • Beginner and Intermediate classes are safe choices. If you want more challenges and enjoyment in workouts, go for the harder ones.


When talking about hard instructors, we don’t mean that they are harsh on you. Instead, they will give you advanced classes with more intense exercises. Yet, they still help you catch up with the pace for the best outcome.

If the practicing beginner lessons are too simple for you Why don’t you try advanced classes? Peloton instructors will always be willing to assist you on this challenging path.

Frequently Asked Questions

1. Who has the hardest classes on Peloton?

The answer differs depending on your targeted class type. Here are our recommendations;

  • For cycling: Kendall Toole and Olivia Amato
  • For running: Jess Sims and Becs Gentry
  • For yoga: Ross Rayburn and Anna Greenberg
  • For strength: Tunde Oyeneyin and Rebecca Kennedy

2. Who is the easiest Peloton instructor?

If you are looking for beginner classes, these instructors will be your best decisions:

  • For cycling: Cody Rigsby
  • For stretching: Hannah Corbin
  • For yoga: Dennis Morton
  • For cardio: Olivia Amato
  • For running: Matt Wilpers
  • For Power Zone Endurance: Ben Alldis
  • For strength: Andy Speer

3. Who is the most difficult Peloton yoga instructor?

Ross Rayburn is a nice choice if you need to improve your yoga practices. He will teach you more complex skills in yoga, but his 20-year experience can aid you in handling advanced classes easily.

4. Who is the hardest Peloton bike instructor?

Kendall Toole is the hardest bike instructor. He offers you many classes with an average difficulty level of 8.28.

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