Academic Leaders Meetup: Boston | Toddle
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Academic Leaders Meetup: Boston 2026

Forging connections, deepening leadership

Academic Leaders Meetup Boston 2026 banner
October 29, 2026 | 9:00 AM - 4:00 PM
October 29, 2026
9:00 AM - 4:00 PM
Venue: The Loft on 2
Academic Leaders Meetup Boston 2026 banner

Event overview

Independent schools have long valued teacher independence and professional judgment. But for students, that can mean moving between classrooms with completely different expectations, systems, and learning experiences. Most academic leaders know this tension well. How do you create more consistency for students without flattening the autonomy and creativity that make independent schools special?

This gathering brings together independent school leaders from across the country, including peers from Shady Hill School and Beaver Country Day School, together to wrestle with exactly that challenge. Designed in partnership with Mastery Transcript Consortium, Authentic Education, and R.E.A.L. Discussion, the day is built around conversation, practical examples, and the shared challenge of building systems that can actually sustain great teaching.

Your seat is free because the work matters. Schools move further when leaders have space to think together.

This event is designed for:

Academic Leaders
Directors of Innovation
Academic Technology Leaders
Directors of Teaching & Learning
ALF Meetup Boston practitioner speakers
6+

Practitioner
speakers

ALF Meetup Boston local leaders
70+

Local
leaders

ALF Meetup Boston interactive sessions
5

Interactive
sessions

Register here for Academic Leaders Meetup for free

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Key topics

A human-centered approach to academic leadership

A human-centered approach to academic leadership

Explore best practices in documenting and reporting on learning

Explore best practices in documenting and reporting on learning

Real conversations with local leaders sharing stories and strategies

Real conversation with local leaders sharing their stories and strategies

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Join academic leaders from leading independent schools

The Browning School
Carrol School
Dwight School
Wooster School
The Windward School
Lib ISB
Trinity School

Why attend

Because lasting change takes collective vision.

Connect

Connect

Build meaningful relationships with fellow academic leaders navigating similar challenges.

Explore

Explore

Examine the ideas, tensions, and shifts shaping the future of learning and leadership.

Strategize

Strategize

Built-in reflection and action-planning time helps you turn ideas into next steps.

Lead

Lead

Strengthen your capacity to guide change while staying grounded in your school’s mission and values.

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Frequently Asked Questions

No! The Academic Leaders Meetup: Boston is a completely free event. We value and appreciate all you do for your learners and this event is our way of thanking you!

The Academic Leaders Meetup: Boston is a free, in-person event hosted at the Loft on 2 in Boston. It’s designed specifically for academic leaders in schools and districts who are thinking deeply about how to shape the future of teaching, learning, and assessment./p>

We’d love for you to join us for the full day of learning, connection, and conversation. That said, we know school leaders have packed schedules, and your time is valuable. You’re absolutely welcome to attend the sessions that align best with your interests and availability. Your presence, even for part of the day, would be truly appreciated.

All participants who attended Academic Leaders Meetup: Boston will be provided with a learning certificate from Toddle.





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Built for teachers, by teachers, Toddle is an AI-powered teaching & learning platform for progressive K-12 schools and districts. Going beyond a typical LMS, Toddle helps you streamline all your work – from curriculum planning and assessments to progress reports and school-home communication. 2,500+ schools and districts across the world trust Toddle to help teachers reclaim valuable time for what matters most – teaching.

Built for teachers, by teachers, Toddle is an AI-powered teaching & learning platform for progressive K-12 schools and districts. Going beyond a typical LMS, Toddle helps you streamline all your work – from curriculum planning and assessments to progress reports and school-home communication. 2,500+ schools and districts across the world trust Toddle to help teachers reclaim valuable time for what matters most – teaching.

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Progress Reports Assistant

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Writing Assistant

Generate high-quality first drafts for your announcements, messages, incident reports & more in a click

Save time and elevate your practices with personal AI assistant

World’s most powerful AI suite for K-12 schools

Save up to 10 hours every week. Streamline your work, amplify your impact.

Curriculum Design Assistant

Built to elevate every stage of curriculum design - from courses to units to lessons

Curriculum Design Assistant
Assignment Builder

Give Toddle AI broad strokes and generate worksheets, questions, assessment tools & more in seconds

Assignment Builder
Feedback & Grading Assistant

Let a smart AI assistant take the first pass at evaluating student work, and cut your grading time in half

Feedback & Grading Assistant
AI Tutors

Let students chat with Plato, practice French & debug code with AI tutors. Personalise help and feedback

AI Tutors
Progress Reports Assistant

Write reports in minutes. Synthesise student data into personalised, evidence-based comments

Progress Reports Assistant
Writing Assistant

Generate high-quality first drafts for your announcements, messages, incident reports & more in a click

Writing Assistant

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Adam Hellebuyck
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Director of Instructional Technology, The Mount Vernon School, Atlanta
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