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Dean of Students for an Innovative Private Academy

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About the SailFuture Academy

The SailFuture Academy is a purposefully disruptive, private nonprofit high school in St. Petersburg, Florida. Our mission is to empower at-risk students to achieve economic freedom and social mobility through character development and pragmatic, project-based learning.

SailFuture Academy operates on a year-round calendar with 5 terms to provide meaningful breaks to students and faculty throughout the year. During each 6-8 week term, students are led through integrated coursework in business, technology, science, math, and language arts. Students also participate in (2) full-day learning labs in Construction and Maritime settings per week.

Dean of Students Job Description

In our search for a Dean of Students, SailFuture is seeking a passionate and experienced leader who shares our vision for project-based technical education and our core values, including the commitment to serve hard-to-reach youth and the use of sailing as a platform for character development. The Dean of Students oversees curriculum, school culture, teacher development, and enrollment efforts.
The SailFuture administrative team provides facility management, marketing, finance, HR, legal, technology, and risk management. The Dean of Students will report to the Chief Executive Officer of SailFuture. This is a year-round position and typical working hours are 730am - 5pm The Dean of Students will take ownership of the design of the curriculum, and the formation of the culture and tone of the school.

● Assist with student recruitment and enrollment
● Lead the design and development of project-based learning curriculum and lesson plans
● Lead teacher training and onboarding
● Lead school culture efforts, including the implementation of student professionalism scores and
the crew system
● Act as the lead administrator for student behaviors and discipline
● Manage student bussing and transportation logistics
● Develop the framework and criteria for competency-based high school graduation
● Act as the primary point of contact for student families
● Assist with DOE, SUFS, and accreditation compliance efforts
● Assist with recruiting community partners and volunteers
● Build and steer a positive school culture rooted in our core principles
● Develop strategic partnerships with middle schools for enrollment

The ideal candidate:
The ideal candidate should be eager to begin, and capable of sustaining, the work needed to build a legacy project and should meet the following criteria:
● Has a successful track record working with at-risk youth
● Experience leading and managing teams
● Experience facilitating project-based learning
● Passionate about reimagining education
● Committed to technical, hands-on learning
● Committed to maritime education
● Inspired by the SailFuture Mission
● Collaborative in their approach
● Flexible and able to thrive in a start-up environment
● Willing and able to commit to building a legacy project
● Entrepreneurial in their thinking and a creative problem solver
● Lead by example and be excited to work in the trenches

● $50,000 salary
● Performance bonus based on annual performance
● $250 per month employee health contribution
● 401k with 6% match
● 20 days PTO (accrual)

Or, know someone who would be a perfect fit? Let them know!

Perks and Benefits

  • 401k with 3-6% employer match

  • Paid Time Off and Sick Days

  • $250 Monthly Health Insurance Contribution

  • Access to sailboats, powerboats, and kayaks

  • Part of dynamic and integrated teams

  • Flexible Work Schedules

Who We Are

We're a small but mighty agency with a 'whatever it takes' mentality.

Our approach to social work is complex and requires dynamic, passionate leaders to bring all their skills to the table.

We're committed to each other as much as we are to our kids, and protect the family dynamic within our motley crew.


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