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The Winchendon School

The best college prep school for students with significant unrealized potential

Learning Strategists

Ashley Paulson

Ms. Paulson brings to Winchendon a strong background in kinesiology, health, fitness, coaching – and supporting students as a tutor.   She understands boarding school having attended and then returned to work at Culver Academies.  And she knows hockey!   Ms. Paulson played at Culver, then went on to be a leader of the D1 program at the University of North Dakota, before returning to the boarding school world where she has coached and taught.  She also receives high marks for knowing what it takes for players to get ready to compete at the highest levels.  Ms. Paulson will also be helping Wapiti develop their “academic muscles and habits” as a Learning Strategist in the Hatch Program.

Favorite Quote: “Man in the Arena” (famous speech by Theodore Roosevelt)

Superpower of choice: Teleportation. No one likes long travel days.

Hero: My parents. They both have worked so hard to support and provide the best opportunities for my sister and me.

Famous person that Ms. Paulson would most like to meet: Taylor Swift

Favorite pastime: hiking, trail running, working out and spending time with family.

“Bucket List” trip that Ms. Paulson would like to take: Backing around Europe

“Go to” comfort food: Chicken pot pie

Michael Santos

In addition to his new wife Anne, Coach Santos brings to Winchendon extensive experience in lacrosse coaching, recruiting, and college placement.  Prior to joining the Winch team, Coach Santos has held coaching and leadership roles including at Next Level, St. Albans School (DC) and New Canaan (CT) High School.  He has also started his own consulting business, through which he has recently worked with several Wapiti student athletes.  Mr. and Mrs. Santos have recently relocated to Winchendon from the Washington, DC area.

Superpower of choice: Flying

Song to start the day: “Burning Up” by Jonas Brothers

Famous person that you would most like to meet: Vin Diesel

Favorite pastime: Pickleball

“Bucket List” trip that you would like to take: Greece

“Go to” comfort food: Chicken Parmesan

Which Winch ColLAB or course would you like to take? Pickleball

Kara Santoro

Ms. Santoro describes herself as “teaching enthusiastically and using the knowledge she gained from previous coaches to keep a positive and competitive family culture for her teams.”  This philosophy certainly informed her work during her first year at Winchendon, and, as a result of her great presence and skill, Ms. Santoro was named Head Coach of the 19U girls hockey program for the coming year.  And her Learning Strategies feel just as positively about her as her players do.

When off duty, Ms. Santoro enjoys playing roller hockey and deck hockey or will find herself indulged in the Marvel Cinematic Universe.

Favorite Place and Book: My favorite place is Lake George, NY. I travel there every year with my family and many of our family friends. Every year we find something new to do and explore, but we always make sure to leave a lake day or two for boating and lounging.   A book that I found myself reading there is Relentless by Tim Grover. The book speaks to competitive athletes and how they do what they do. Many of the lessons described can be translated off the ice and implemented into a person’s mindset for life.
Bucket List: My major bucket list item is to skydive in all 50 states. I love to travel and I would love to see all of the USA – what better way to do it than 10,000 feet in the air! My first jump was actually in 2020 in Saratoga, NY during our annual trip to Lake George.

Go-to Comfort food: My go-to comfort food is hands down Chipotle.

Superpower of Choice: I always love this question because there are so many possibilities and weighing the pros and cons of each could take a lifetime. But, I think I would have to go with teleporting. The thought of not having to fly on a plane or drive for hours (or days) is incredible. It would also make getting to all 50 states to skydive a lot easier!

Phil Simplicio

Phil is passionate about helping others and getting the best out of someone. He is an avid Boston sports fan, a UCONN basketball fan, and a Notre Dame football fan. As a teacher, he is excited to be at Winchendon. At Bates College, he majored in Economics with a minor in Religious studies and a concentration in Education. He was also a leader on the Bates football team, and loves golf, cribbage, and reading.

A favorite place to visit and the books you would take there? My favorite place in the world is Popponesset Cape Cod. I would bring my biographies on Bill Belicheck and Willie Mays and sit right by the ocean with my toes in the sand. 

On the bucket list?  Get to a game at Notre Dame stadium. 

Hero/heroine? My Grandpa, Richard Roche. He is the best man I know.  

Song to start the day? That’s Alright by Just Like Us 

Bernard Lipat

Bernard Lipat

This past spring, Bernard completed his Ph.D. in Applied Physics and Applied Mathematics with a concentration in Atmospheric Science at Columbia University in the City of New York and at NASA/GISS as a NASA Earth and Space Science Fellow. His dissertation was entitled “Quantifying the Linkages between Clouds and the General Circulation of the Atmosphere”. At Columbia University, Bernard served as co-chair of the department social committee and co-founded qSTEM — the organization for queer graduate students in STEM. Before that, Bernard completed his undergraduate degree from New Jersey City University with a double major in Mathematics and Psychology as well as a minor in Computer Science. There, he served as President of the Psychology Society, President of the Math Club, and President of KME — the mathematics honor society.

Globetrotting adventure: Brasil!

Go-to comfort food: Mac & Cheese

Favorite place and books on hand: Any play by Ibsen, read while cuddling my dog

Song to start the day: I feel better – Hot Chip

Superpower of choice: Telekinesis

Madeline Legro

Maddie moved to New York in 2016 after receiving her Bachelor of Arts in Ethnomusicology and Classical Studies from Bates College. Since then, she’s worked full-time as an audio engineer and part-time as a barista, bookworm, and folk musician. Maddie is thrilled to be an incoming faculty member at TWS Brooklyn!

Which Winchendon class would you most like to take: I’d most like to take “The Sword, Pen, and Arrow: Freedom is Born out of Function” ColLAB!

Superpower of choice: Shapeshifting!

What you’re looking forward to the most this year: I’m most looking forward to learning and growing with Winchendon Students, designing ColLABs, and diving deeper into social justice in Brooklyn.

On the bucket list: See the Aurora Borealis, travel to Timbuktu by Jeep, record a studio album.

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