Dean of Students

About SailFuture Academy

SailFuture Academy is a purposefully disruptive, non-profit private high school in St. Petersburg, Florida, serving youth who have faced significant challenges.

As a nonprofit organization, we are reimagining education to empower students with the character, skills, and real-world experiences they need to achieve economic freedom and social mobility.

Our students don't just learn-they build, lead, create, and grow. We are searching for an individual passionate about transformative education, community impact, and working alongside a team that truly cares.

About the Role

The Dean of Students plays a pivotal role in shaping a positive, supportive, and high-expectation culture across our campus.

You'll be a driving force behind student growth-emotionally, socially, and academically-and will help students navigate their journeys toward adulthood and independence.

This is more than a job; it's a chance to be part of a team that believes every young person deserves to thrive.

Key Responsibilities

Culture & Community Leadership

• Cultivate a school culture rooted in respect, accountability, and purpose.
• Lead student behavior systems and implement individualized growth plans.
• Build strong, trusting relationships with students and their families.
• Promote a safe and inclusive learning environment-physically, emotionally, and intellectually.

Engagement & Partnerships

• Design and lead engaging on- and off-campus student activities.
• Recruit and manage volunteers and community partners to enhance learning.
• Establish strategic partnerships with local middle schools to support enrollment pipelines.

Operations & Logistics

• Oversee key operational areas of the school, including:
  
  • Daily transportation and student bussing
  • School lunch program and food services
  • Student scheduling and enrollment
  • Inventory and supply management

What We're Looking For

• 3-5 years of professional experience, ideally in education, youth development, or leadership
• Bachelor's Degree required
• Proven leadership track record with demonstrated growth and responsibility
• Strong communicator with experience in relationship-building roles (e.g., customer service, sales, coaching)
• Independent, self-motivated problem solver with strong critical thinking skills
• Committed to continuous personal and professional growth
• Professional, confident, and approachable demeanor

Compensation & Benefits

• $250/month health care reimbursement
• 401(k) with 6% employer match
• 15 days of paid time off per year (accrued)
• A dynamic, mission-driven team that supports and challenges you

Program SailFuture Academy Locations St Petersburg