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Founding Head of School - SailFuture Maritime Academy

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Founding Head of School

SailFuture is recruiting an entrepreneurial school leader to launch a trauma-informed vocational high school in St. Petersburg, FL as part of SailFuture’s existing network of social services.

About SailFuture
SailFuture was founded in 2013 as a volunteer after school mentorship program using sailing as a platform to mentor students in a title 1 drop-out prevention program.

In 7 years the organization has grown to a dedicated team of more than 30 professionals and is recognized as a leader in Florida’s Child Welfare system.

SailFuture is based in St. Petersburg, FL and operates 5 distinct programs ranging from residential foster care to adventure-based therapeutic services. Last year SailFuture served more than 200 children and families.

Building upon our work in experiential learning and trauma-informed care for hard to reach youth, SailFuture is excited to launch a project based nonprofit private school in St. Petersburg, FL in the Fall of 2021.

The SailFuture Board and leadership team are fully committed to the development of this unique school model. The organization has raised more than $2M in private funding, acquired a 25,000 sqft facility, and garnered widespread community support through existing partners.

About the SailFuture Maritime Academy
The SailFuture Maritime Academy is a private nonprofit vocational high school for low-income families and youth in foster care in St Petersburg, FL. The school will serve students in grades 9th - 12th who have become disengaged in traditional public school settings.

The school will focus on technical education and prepare students to enter the maritime, culinary, and construction workforces. Students will participate in a blend of on-the-job training and project based learning activities to master the core competencies required for graduation.

Our commitment is to match each graduating student with a living-wage job through one of our employment partners. Students will select an industry preference when they enter the upper school and begin industry-specific training in the 10th grade.

Students will develop a Student Growth Plan in 9th grade that outlines key milestones for their high school graduation. Each student’s plan is made up of STEM (Science, Technology, Engineering, and Math), Liberal Arts, and technical education milestones achieved through the completion of mastery projects.

Student achievement will be measured with a student growth transcript that measures mindset, technical skill, knowledge, and social-emotional ability.


Head of School Job Description
The Founding Head of School will launch the SailFuture Maritime Academy, a private nonprofit technical high school for low-income families and youth in foster care in Pinellas County.

In our search for a founding Head of School, 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 Head of school will serve as the Chief Executive of the school and lead both the academic and operational functions of the school. SailFuture will provide back office functions, including marketing, finance, HR, legal, technology, and insurance. The head of school will report to the Executive Director of SailFuture.

The Head of School will take ownership of the development of the physical campus, the design of the curriculum, and the formation of the culture and tone of the school. 

The Head of School will be hired in February 2020 in advance of the Fall 2021 campus opening. 

Year 0 Responsibilities (February 2020 - August 2020): 

  • Recruit 30 scholarship-eligible students between February 2021 and August 25, 2021
  • Develop the project-based learning curriculum for the first school year
  • Develop the STEM and Liberal arts curriculum for the first school year
  • Assist with the design and furnishing of classrooms and other school spaces
  • Finalize with the design and framework for student growth plans
  • Design the framework for an effective student rewards system
  • Design the framework for an effective student disciplinary system
  • Develop a student bussing and transportation plan
  • Develop the framework and criteria for competency-based high school graduation
  • Design and build the framework for mastery projects
  • Recruit and train 4 Learning Coaches to form the core team for the founding year
  • Lead community outreach efforts

Year 1+ Responsibilities:

  • Work with the Board to raise private funding for operations 
  • Recruit students per the school’s established enrollment plan
  • Recruit community partners to serve as volunteer and part-time subject matter expert learning coaches
  • Develop strategic partnerships with elementary and middle schools for enrollment
  • Facilitate weekly staff meetings with all staff
  • Oversee the development and implementation of curriculum
  • Oversee recruitment, selection, retention, and development of all academic and operational staff
  • Ensure annual DOE and SUFS school compliance 
  • Build and steer a positive school culture rooted in our core principles
  • Manage student bussing and transportation
  • Serve as a Crew Sponsor to 1 group of students
  • Serve as a mastery project coach for up to 2 projects per year
  • Manage AmeriCorps members
  • Lead community outreach efforts
  • Oversee and manage the school budget

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
  • Has a successful track record raising private funding
  • 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


  • Salary commensurate with experience
  • 401k 
  • Health insurance contribution
  • PTO


The Facility
2154 27th Ave. N. 
St Petersburg, FL

  • 25,000 sqft building 
  • 13 classrooms
  • 4 Offices
  • Teaching Restaurant
  • Vocational Workshop
  • Coffee Shop Lounge


Student Body
The school will serve students from 9th - 12th grade and is tuition-free for all students eligible for McKay, Step Up For Students, HOPE, and Family Empowerment scholarships. The annual tuition for private pay students is $16,500 per year.

Prospective students will interview with an admissions panel of current students and faculty to determine admission. All admitted students must demonstrate a desire to attend the school.

Enrollment PlanScreen Shot 2020-12-25 at 5.41.54 PM.png

Faculty Design
The faculty will be made up of ‘Learning Coaches’ who specialize in three areas:

  1. STEAM Facilitators - Science, Technology, Arts, Math
  2. Liberal Arts Facilitators - Reading, Writing, History, Social Sciences
  3. Technical Education Facilitators - Culinary, Maritime, Construction

Each Learning Coach will design and facilitate mastery projects in their areas of interest and expertise. In addition to facilitating mastery projects for all students, each Coach acts as the Crew Sponsor for a group of 12 students. 

Crew Sponsors manage each student’s growth plan. This includes meeting 1:1 with each student for weekly performance reviews and mastery planning sessions, as well as forming a positive culture and familial-bond within their Crew. 

Academic Model
Each student works with their Crew Sponsor to design an individual growth plan, which outlines key milestones that the student must achieve prior to obtaining their high school diploma. 

Students participate in 2-4 week mastery projects aligned with their student growth plan. Each project culminates in a capstone activity where the student demonstrates their level of mastery of the project’s subject matter. 

Competency-Based Evaluation
Learning Coaches evaluate student performance in mastery projects through a student growth transcript that measures four domains: Mindset, Knowledge, vocational expertise, and life skills.


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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