Heads & Tales Live NYC

Transatlantic Perspectives from Top Schools

Roosevelt House, NYC

Monday 16th November
5:45pm for 6pm Q&A, 7:15pm drinks

Horace Mann and Choate Rosemary, Eton and Wellington.

Join four of the world’s leading headmasters from both sides of the Atlantic for a rare, candid conversation on what defines a great education. 

This intimate panel with limited attendance brings parents inside the thinking, leadership and day-to-day realities of exceptional schools. 

Whether you’re aiming high for your own children, or curious to hear how the best institutions operate, this is a unique opportunity to hear directly from those at the helm, and to ask the questions that matter most. 

Roosevelt House offers capacity for just over 100 attendees, with a networking drinks with our speakers to follow the event. 

Dr Tom Kelly
Horace Mann

Dr Alex Curtis
Choate Rosemary

James Dahl
Wellington College

Simon Henderson
Eton College

Hosted By

Henry Faber

Head Boy at Eton College before studying at Oxford University, Henry has spent a decade enabling mentoring for more than 10,000 students, while advising families on how best to support their children to access and thrive within the world’s best schools and universities. Henry was recognised as a Forbes 30 Under 30 founder for social entrepreneurship alongside co-founder and friend Walter Kerr. He lives in New York City, working closely with NYC-based families, and leading independent and public sector schools across multiple continents. 

Meet the speakers

  • Dr Tom Kelly

    Horace Mann School

    Dr. Tom Kelly has served as Head of School at Horace Mann School for over 15 years, one of America’s top preparatory schools. Born in D.C. and raised in Westchester County, NY, he holds degrees from Columbia University and Fairfield University. 

  • Smiling woman with blonde hair wearing a black blazer and white top standing outdoors near a brick building with large windows.

    Dr. Alex Curtis

    Choate Rosemary Hall

    Dr. Alex Curtis, born and raised in the UK, is Head of School at Choate Rosemary Hall, home to 850 boarding and day students in Wallingford, CT. He has a Ph.D from Princeton and leads from a background of teaching architectural history.

  • A middle-aged man in a suit with a blue tie, smiling, standing inside a warmly lit library with bookshelves in the background.

    Simon Henderson

    Eton College

    Simon Henderson has been Head Master of Eton College, the UK’s most famous school, since 2015 - becoming its youngest headmaster at 39. Educated at Winchester and Oxford, he taught History at Eton from 2001, and eventually led Bradfield College before returning as Head Master. He will retire from his position at Eton in Summer 2027. 

  • James Dahl

    Wellington College

    James Dahl is the 15th Master of Wellington College, appointed in 2019 as the school’s first internally appointed Master. Educated at Cambridge (Classics), he began at Brighton College and Repton, before joining Wellington in 2013, serving as Director of Admissions & Marketing and Deputy Head Pastoral before becoming Master. 

Introducing Charles Russell Speechlys

Charles Russell Speechlys is an international law firm with a focus on private capital, at the intersection of personal, family and business. We have a broad range of skills, collective legal expertise and an international outlook across the full spectrum of business and personal needs. 

Our ability to understand people makes us who we are. We work together to build deep and trusted relationships that deliver meaningful value. We do this with empathy, attention and clarity. No jargon, no attitude. We know what matters.

  • "It was an incredibly informative evening. Henry led the conversation beautifully, allowing the event to be both educational and enjoyable. It was pleasure as well to meet school officials from such venerable secondary schools."

    John Dearie, Director of Secondary School Counselling at Saint David’s School, NYC

  • "Oppidan Education is bringing something fresh and new to NYC with the aim to help children and families. Henry and his team truly care about their work and the people they partner with."

     Colleen Vasey, Director of High School Advising at St. Luke’s School, NYC

  • "An engaging panel and reception that gave U.S. educators valuable insight into the world of top UK schools while fostering meaningful connections."

    Natalie Alterman, Executive Director of ISAAGNY

  • "Education plays a very significant role in determining the people we become and what we do with our lives. More effort needs to be made in helping parents pick the right education for their children and Oppidan seems to be pioneering an answer to that problem."

    James McDonald, NYC Parent