Teacher/Guide - Grades K–5

About Tradewinds School

Tradewinds School is Hawaii's first dedicated elementary school for gifted and profoundly gifted children (grades K-5), launching in Fall 2026. We're not just another rigorous private school—we're building something fundamentally different. Our mission is to serve students with asynchronous development who need true differentiation, not just acceleration or busywork disguised as enrichment.

At Tradewinds, we combine AI-powered adaptive learning with hands-on experiential education, allowing each student to progress at their natural pace without artificial speed limits. We believe gifted children need to be with like-minded peers who understand them, while still receiving age-appropriate social-emotional support. Our goal is to cultivate scholars who maintain their natural curiosity and intellectual fearlessness throughout their educational journey.

As a founding teacher, you'll help shape the culture and educational approach of a school built from the ground up to serve an underserved population. This is an opportunity to move beyond the traditional "faster hamster wheel" approach and create authentic learning experiences that preserve what makes gifted children special.

The Role

As a Teacher/Guide at Tradewinds, you won't deliver lectures or grade worksheets. Instead, you'll facilitate personalized learning journeys for 8-12 students across multiple grade levels, leveraging adaptive learning technology while creating meaningful hands-on experiences. You'll be equal parts mentor, facilitator, and learning architect.

This role requires someone who understands that gifted education isn't about doing more or going faster—it's about going deeper, making connections, and preserving the joy of discovery. You'll work with students who may be performing years above grade level in some areas while needing support in others, requiring sophisticated differentiation and genuine understanding of asynchronous development.

Key Responsibilities

Learning Facilitation

• Guide 8-12 students using AI-adaptive curriculum platforms combined with project-based experiential learning
• Facilitate multi-age learning groups that allow students to work at their natural pace without artificial constraints
• Design and lead hands-on workshops that connect academic content to real-world applications
• Create intellectually rigorous project based experiences

Student Development

• Mentor gifted learners through the unique challenges of asynchronous development
• Help students develop genuine competence through appropriately challenging work, not busywork
• Foster peer relationships among intellectually curious students who often struggle to find like-minded friends
• Support students in developing a "personal best" mindset rather than unhealthy competition
• Guide students in setting and achieving ambitious personal learning goals

Classroom Leadership

• Maintain an environment that preserves natural curiosity and intellectual fearlessness
• Implement positive behavior support that respects individual differences
• Create structured flexibility that provides security while allowing for exploration
• Balance individual advancement with collaborative community building

Parent Partnership

• Communicate regularly with families who deeply understand their children's unique needs
• Provide transparent updates on student progress across multiple developmental domains
• Partner with parents who are actively engaged in their children's education
• Support families navigating the challenges of raising gifted children

Curriculum Innovation

• Collaborate in developing and refining our hybrid AI-adaptive and experiential curriculum model
• Contribute insights from direct student observation to improve learning approaches
• Participate in our educational "brain trust" with advisors from leading gifted institutions
• Help establish best practices that will define Tradewinds' educational philosophy

What Success Looks Like

• Students maintain their love of learning and intellectual curiosity
• Each child progresses at their natural pace without hitting artificial ceilings
• Learners develop both deep competence and broad connections across subjects
• Students feel understood and supported by peers and adults
• Families see their children thriving academically and social-emotionally
• The classroom becomes a joyful community of engaged learners

Ideal Candidate Profile

Required Qualifications

• Bachelor's degree in any field (advanced degree preferred but not required)
• 2+ years of experience working directly with elementary-age children in an educational capacity
• Demonstrated understanding of gifted education and asynchronous development
• Comfort with educational technology and willingness to integrate AI-adaptive learning platforms
• Legal authorization to work in the United States

Strongly Preferred

• Experience with gifted populations, particularly 2E (twice-exceptional) learners
• Background in constructivist/progressive education approaches
• Familiarity with project-based and experiential learning methodologies
• Understanding of social-emotional needs of gifted children
• Experience with multi-age groupings or differentiated instruction
• Personal experience as a high performer, gifted individual, or parent of gifted children

Personal Characteristics

• Intellectual curiosity that matches our students' hunger for learning
• Flexibility to adapt to individual student needs moment by moment
• Emotional intelligence to support students through frustration and perfectionism
• Growth mindset with willingness to iterate and improve continuously
• Collaborative spirit as we build this school together
• Genuine warmth combined with high standards
• Systems thinking to see connections across disciplines
• Stamina for the intensity of working with gifted learners

What We Offer

Compensation & Benefits

• Competitive salary: $65,000 - $85,000 based on experience
• Comprehensive health benefits (medical, dental, vision)
• Professional development budget for conferences and training
• Retirement plan with employer matching
• Tuition remission for employees' children
• Relocation assistance available for mainland candidates

Professional Environment

• Small class sizes (8-12 students) with additional support staff
• Access to cutting-edge educational technology and AI platforms
• Collaboration with educational leaders from top gifted institutions nationally
• Significant autonomy in designing learning experiences
• Direct influence on school culture and policies as founding faculty
• Regular planning time and professional collaboration built into schedule

Growth Opportunities

• Leadership pathway as school expands to middle school
• Opportunity to develop expertise in gifted education
• Potential to present at conferences and contribute to the field
• Mentorship from nationally recognized gifted education experts

The Selection Process

1. Application Review - Submit cover letter and resume
2. Initial Interview - 30-minute video conversation with founding team
3. Teaching Demonstration - Interactive session with sample learning scenario
4. In-Depth Interview - Discussion of educational philosophy and approach
5. Reference Checks - Conversations with previous supervisors/colleagues
6. Final Interview - Meet with board members and advisors
7. Offer - Competitive package with time to consider

How to Apply

Please submit the following materials:

Cover Letter addressing:

• Your understanding of and experience with gifted learners
• Your philosophy on balancing technology with hands-on learning
• Why being part of founding a new school appeals to you
• What unique strengths you'd bring to our community

Resume

Highlighting relevant teaching experience and any work with gifted populations.

Commitment to Diversity

Tradewinds School is committed to building a diverse and inclusive community. We believe gifted children come from all backgrounds and that our school should reflect Hawaii's rich cultural diversity. We strongly encourage applications from candidates of all ethnicities, backgrounds, and life experiences. We do not discriminate on the basis of race, color, religion, gender, gender expression, age, national origin, disability, marital status, sexual orientation, or military status.

Questions?

For more information about Tradewinds School, visit tradewinds.school or email info@tradewinds.school with questions about the position or school.