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