Field Staff

Sam Adair

Lead Instructor

Simon Beckford

Sailing Program Coordinator

Pronouns: He/They

Hometown: Clifton, ME

Started with HIOBS: 2011

Fun facts: Simon is a Photographer and Artist as well as a HIOBS Instructor, and enjoys personal adventures sailing a small dory on the coast of Maine or hiking and backpacking in Maine and Scotland.

Jonathan Bickford

Lead Instructor

Pronouns: He/Him/His

Hometown: Kittery Point, ME

Started with HIOBS: 2012

Fun fact: Maine is the only US state to border one ocean, one country, and one other state.  

Barton Blankenship

Lead Instructor

Pronouns: He/Him/His

Hometown: Palmetto, FL

Started with HIOBS: 2008

Fun fact: On the sailing part of his spring semester, Bart had a 10’ Hammerhead swim up to him and stop at 6’. He had a foot cramp and swam back to the boat with one leg looking wounded. Everyone cracked up when Bart got back in the boat because he swam so poorly.

Courtney "Beans" Boucher

Lead Instructor

Pronouns: She/Her/Hers

Hometown: Annapolis, MD

Started with HIOBS: 2022

Tucker Brown

Land Program Coordinator

Sarah "eSBee" Buhlman

Lead Instructor

Pronouns: They/Them

Hometown: Marriottsville, MD

Started with HIOBS: 2012

Fun Facts: eSBee is a health teacher in Portland, ME when they're not working for HIOBS, and are currently in grad school for Public Health. They are finally fulfilling lifelong hopes of learning how to surf and mountain bike in the past couple of years! 

John "Sockeye" Calogero

Lead Instructor

Pronouns: He/Him/his

Hometown: San Juan Islands

Started with HIOBS: 2011

Fun fact: Sockeye came up with the phrase, "It is only trivia out of context" while teaching some nautical detail. 

Lucy Chatfield

Instructor

Abigail Colby

Instructor

Pronouns: She/Her/Hers

Hometown: Midcoast Maine

Started with HIOBS: 2023

Fun fact: 

Ben Cornell

Instructor

Erin Cunningham

Instructor

Pronouns: She/Her/Hers

Hometown: Weymouth, MA

Started with HIOBS: 2021

Fun facts: Erin enjoys spending time swimming, hiking, skiing, running, and anything else outside! 

John Donovan

Lead Instructor

Preferred Pronouns: He/Him/His

Hometown: Hanover, NH

Started with HIOBS: 1976

Fun fact: John skippered a 35' sailboat on two short-handed transatlantic crossings.

Alexis Doroski

Logistics Coordinator

Lena Downes

Instructor

Sofia Fea Ruiz

Instructor

Haley "Bird" Ferrer

Instructor

Pronouns: She/Her/Hers

Hometown: West Chester, PA

Started with HIOBS: 2022

Fun fact: Bird has never flossed!

John Fisher

Instructor

Gray George

Instructor

Pronouns: She/They

Jacob Grant

Logistics Manager

Pronouns: He/Him/His

Hometown: Austin, TX

Started with HIOBS: 2024

Fun fact: Jacob won a hot dog eating contest when he was 12.

Lucy Hayward

Instructor

Preferred pronouns: She/Her/Hers

Hometown: Rockport, ME

Started with HIOBS: 2021

Fun facts: Lucy ran her first half marathon in Bhutan while she was studying abroad. Since then she has run two more!

Morgan Hinson

Lead Instructor

 Pronouns: She/Her/Hers

Hometown: Northern Wisconsin

Started with HIOBS: 2019

Fun fact: Like many Outward Bound instructors, Morgan looks forward to someday having a dog and a garden of her own. For now, she has four shared tomato plants and likes thinking of potential dog names.

Sheldon Ito

Lead Instructor

Beth Jackson

Lead Instructor

Hometown of Bloomington, IN

Instructor since 2007

Fun Fact: Beth once had a dog that would steal Halloween candy and hide it under pillows. She never opened the candies so it was like getting presents all the time!

Ray Jackson

Instructor

Pronouns: He/Him/His

Hometown: New Orleans, LA

Started with HIOBS: 2022

Fun fact: Ray is a published poet and playwright.

Liam Janson

Instructor

Mathias Klingemann

Instructor

Sophia Lacambra

Instructor

Preferred pronouns: She/Her/Hers

Hometown: Seattle, WA

Started with HIOBS: 2021

Fun facts: Sophia studied Environmental Science at Barnard College and loves being on or as close to the water as possible! Some of her favorite activities are running, reading on the beach, and listening to and playing music. 

Allison Lichtenstein

Instructor

Pronouns: She/Her/Hers

Hometown: Hanover, NH

Started with HIOBS: 2023

Fun fact: Allison's favorite animal is a highland cow (looks like a cow/ golden retriever mix!).

Ben Lidoski

Instructor

Olivia Lord

Lead Instructor

Pronouns: She/Her/Hers 

Hometown: Cambridge, MA

Started with HIOBS: 2021

Fun facts: Olivia will be sailing and rowing in the Race to Alaska for the first time this year (2022) with Team Sockeye Voyages! When she's not working for HIOBS, you can find her hanging out on oyster farms in Cape Cod or on SEA Semester tallships in the South Pacific and North Atlantic. Olivia is a huge fan of stargazing and cloud spotting. 

Heyward Main

Instructor

Pronouns: He/Him/His

Hometown: Charleston, SC

Started with HIOBS: 2023

Fun fact: Heyward has had the same water bottle since 4th grade.

Marissa Mann

Instructor

Kayla Markwardt

Instructor

Pronouns: She/Her/Hers

Hometown: Ithaca, NY

Started with HIOBS: 2023

Fun fact: Kayla can ride a unicycle (sometimes).

Dave Menges

Senior Lead Instructor

Preferred pronouns: He/Him/His

Started with HIOBS: 1989

Hometown: Cleveland, Ohio

Fun fact: Dave was an elementary school principal at an all-boys school in Richmond, VA for 17 years. He's currently serving as the Head of School for another independent school in Richmond.

Rachel Milito

Lead Instructor

Chris Myrick

Burnt Island Program Coordinator

Pronouns: He/Him/His

Hometown: Hingham, MA

Started with HIOBS: 2021

Fun facts: Chris loves being on his feet and working with his hands. Some of his favorite pastimes include pool, frisbee, hacky sack, and watching movies. When he's outdoors you can find him hiking and climbing in the mountains, cross country skiing, running along a park trail, or maybe even sailing a pulling boat! 

Jay O'Hara

Instructor

Jackie O'Malley

Kitchen Coordinator

Pronouns: She/Her/Hers

Hometown: CT

Started with HIOBS: 2024

Fun fact: Jackie has sailed over 20,000 nautical miles! She loves long walks on the ocean.

Luke O’Neill

Lead Instructor, OBP Facilitator

Pronouns: He/Him/His

Hometown: South Portland, ME

Started with HIOBS: 1990

Fun Facts: Luke always bring a “spoon-tula” - a combination spoon and spatula - with him on course to capture every last morsel of food from bowls, pots, and pans.  Food is fuel! 

Anna Parker

Lead Instructor

Pronouns: They/Them/Their

Hometown: Boston, MA

Started with HIOBS: 2014

Fun fact: In their free time, AP dances with a lion and dragon dance troupe in Boston.

Jeremy Reinertson

Assistant Program Director

Pronouns: He/Him/His

Hometown: Springfield, IL

Started with HIOBS: 2018

Fun facts: Jeremy enjoys long walks on the beach, candlelit dinners, poetry readings, and falling headfirst into gurgling mud pits. He has written three novels, which he holds close to himself like secret treasures locked inside a silver chest.

Nicki Ripple

Lead Instructor

Pronouns: She/Her/Hers

Hometown: Pittsburgh, PA

Started with HIOBS: 2016

Drew Schmid

Lead Instructor

Pronouns: He/Him/His

Hometown: Boothbay, ME

Started with HIOBS: 2019

Fun fact: Drew has a moose skull, an owl's wing, and three raccoon rib bones in his car right now.

Naman Sharma

Instructor

Pronouns: He/Him/His

Hometown: Himachal Pradesh, India

Started with HIOBS: 2023

Fun fact: Naman's name is a Palindrome. 

Sheetal Shelke

MOLI Program Coordinator

Pronouns: She/Her/Hers

Hometown: India

Started with HIOBS: 2024

Fun fact: When in India, Sheetal enjoys being in the Himalayan mountains or looking for big cats in the Indian Tiger Reserves. She is also a snake catcher/rescuer!

Anthony Sousa

Lead Instructor

Pronouns: He/Him/His

Hometown: Tarpon Springs, FL

Fun Fact: "Ant" grew up in Maine, but his life partner loves it sunny, so Florida it is!

Grace Stein

Instructor

Lydia Vanderburg

Lead Instructor

Pronouns: She/Her/Hers

Hometown: Seattle, WA

Started with HIOBS: 2022

Fun facts: Lydia's favorite pastimes are reading science fiction, knitting socks, and messing about in boats. When not working, Lydia can most often be found lying on the ground, examining mosses and small flowers.

Dan Wellehan

Lead Instructor

Tierney Weymueller

Sailing Program Coordinator

Pronouns: She/Her/Hers

Hometown: Alvin, TX

Started with HIOBS: 2022

Fun fact: Tierney loves to put peanuts in her coke! 

Nora Willauer

Instructor

Peals Wrobel

Lead Instructor

Pronouns: She/Her/Hers

Started with HIOBS: 1976

Hometown: Buffalo, NY

Fun facts: Peals used to hitchhike a lot before getting her motorcycle and car. She’s still not a grown-up.

Vidar Zay

Instructor

Lady Sky

Lead Napper

Pronouns: She/Her/Hers

Hometown: Midcoast Maine

Started with HIOBS: 2023

Fun fact: