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A Personalized Approach to Mastering Pickleball with Doug Steinberg, PaddleUp Pickleball, Natick, MA

A personalized approach to mastering pickleball

with Doug Steinberg



During his 35-year career in squash, Doug won multiple Massachusetts state titles in team singles and doubles and was ranked as high as 5th in the state and 54th in the country for players 50 years old and over.


Four years ago,  he discovered pickleball, subsequently tossed all of his squash gear and never looked back!  A consistent medalist at the 4.5 level, Doug is a competitive player who enjoys the fun and comradery of tourneys and recreational play.

While Doug loves to play, he has a greater passion for coaching.  He is known throughout the Metrowest Boston area for being able to break down a player’s stroke, footwork and strategy at any level of play, and find simple and understandable ways to improve all three phases. 


Throughout the journey to improvement, Doug focuses on control, accuracy and consistency while always infusing fun into the sessions. The results of his success with his students can be measured in the dozens of medals his students have won across all levels and ages along with constant referrals from satisfied players.

Learn about Doug, owner of Paddle Up Pickleball, Natick, MA
our mission

The mission of Paddle Up Pickleball School (PUPS) is to guide students on their journey to becoming strong, strategic and adept players. We do this by developing their understanding and foundations of the game, while also honing in on skillset and on-court tools that help lead to successful matches. Servicing Natick, Wellesley, Wayland and MetroWest Boston area, PUPS is quickly building a reputation for making beginners at any age feel welcome to the sport and turning competitive players into champions; we attribute a lot of our success to our ability to coach assertively while also mixing in some fun!


Clinics & Lessons

Private Lessons

1 on 1 coaching focusing on stroke, footwork and decision making.


$85 per hour

(either 60 or 90 minute sessions)

up the river /
down the river

This clinic is for seasoned players who have incorporated dinking, third shot, etc, into their game. 

For 3.25 - 4.0 players.

Play for 12 minutes, the winning team moves up the court, the losing team moves down the court.

Pricing: $30 per person.

Semi-Private Lessons

Coaching focusing on stroke, footwork, decision making and some team strategy. 


Two players $50 per player per hour

(either 60 or 90 minute sessions).

Specialty Clinics

These clinics focus on one or two strokes and are tailored toward the level of players’ play.  An example of a Specialty Clinic is the “Dinks and Thirds” Clinic.


Pricing depends on size of group.

Play with the Pro

The Pro plays a 90 minute session of games and drilling with 3 other similar leveled players.  You find a group of 3 that you want to play with and the session focuses on both strategy and technique.  Multiple games are played along with some drilling mixed in. 


Pricing: $45 per person outdoor

$50 per person indoor.

Parks & Rec

Learn the fundamentals of the game of Pickleball. Recommended for ALL NEW players and players getting back in the game. Includes Grip, ready position, safety, basic overview of shots and footwork drills.  

See Town Sites for Offerings.

Wayland | Wellesley | Natick

recent pups student medalists


Doug has a unique ability to assess every detail of my game quickly and accurately. He then patiently guides me to form better habits and awareness to improve my paddle and grip dynamics, court position, and game strategy. Working with Doug has been a game changer for me.

Aggie M., Wayland, MA

Doug is the best!  I so look forward to my lessons with Doug.  He can see what needs to be tweaked right away and helps make the adjustment.  His teaching skills and knowledge of the game are the best.  He instills confidence all while having fun!

Laura S., Natick, MA

Doug has a thoughtful approach to teaching Pickleball. He watches your strokes and movement very closely and is able to build your skills to move you forward with the game. I worked out physically during the lesson, but most importantly he made me really think about my playing. I am looking forward to my next lesson with Doug!

Elaine D., Natick, MA

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