Dean of Students
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Are you frustrated with an antiquated education system that does not prepare young people for the real world?
Are you confident in your ability to create a culture that deeply engages students in character growth and development?
Do your colleagues often rely on you to find solutions effectively? Do people describe you as someone with outstanding moral character?
If this sounds like you, you may have just found your next work family.
We are searching for a Dean of Students to lead Student Culture and operations at the SailFuture Academy. You guide and lead a student culture in a hands-on project-based learning environment where students are expected to critically think, problem-solve, and grow their character. You will grow our student base and continuously improve school operations. You will be the rock for our students, family, and community.
At the SailFuture Academy, you will find the space, resources, and support to lead a student culture that motivates and inspires students to self-actualize.
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 school culture, enrollment, and school operations. This is a year-round position and typical working hours are 730am - 5pm, Monday through Friday. Additional non-traditional working hours are required to meet student recruitment and parent engagement goals.
The Dean of Students will take ownership of the design of the formation of the culture and tone of the school.
- Lead student and school culture, including the implementation of character growth tools and social-emotional learning rooted in our Guiding Principles
- Have ownership of student recruitment and enrollment
- Be responsible for student behaviors, discipline, and growth plans
- Establish and maintain meaningful relationships and trust with student’s families
- Manage Academy operations including:
- student bussing and transportation logistics
- school lunch program and daily food operations
- student class schedules
- student enrollment
- operations-specific supply inventory
- school maintenance
- Ensure a safe learning environment, both physically and intellectually
- Create off and on-campus student engagement opportunities
- Assist with DOE, SUFS, and accreditation compliance efforts
- Assist with recruiting community partners and volunteers
- Develop strategic partnerships with middle schools for enrollment
- 5-7 years of professional experience
- Record of promotion to a leadership role within an organization
- Technologically proficient and highly comfortable working in a digital environment (Platforms:, Coda, Slack, Notion, Google Docs, Google Admin, etc.)
- Experience in direct communication roles, preferably in customer service or sales
- Self-starter who is able to work independently
- Problem solver with strong critical thinking skills
- Ambition to learn and grow
- Presents a professional and confident manner
Knowledge and Attributes You Bring to the Team:
- Alignment with our core values
- Eager to begin, and capable of sustaining the work needed to build a legacy project
- You lead by example and are excited to work in the trenches
- You possess the GRIT and passion to commit to a long-term legacy project that is bigger than yourself
- You’re entrepreneurial in your thinking and you are a creative problem solver
- You’re collaborative in your approach
- You’re flexible and able to thrive in a start-up environment
- You’re passionate about reimagining education
- You’re inspired by the SailFuture Mission
Standout Applicants May Also Bring:
- Bachelor’s degree
- Experience leading an educational institution
- Performance bonus
- $250 per month employee health contribution
- 401k with 6% match
- 20 days paid time off annually (accrual)
About 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.
The school model leverages integrated coursework in business, technology, science, math, and language arts with practical application labs in construction, maritime, and culinary settings.
Students focus on foundational academic and character development curriculum in 9th and 10th grade and participate in an in-house internship in 11th grade and an external apprenticeship in their 12th-grade year.
- SailFuture Academy
- St Petersburg
401k with 3-6% employer match
Paid Time Off
$250 Monthly Health Insurance Contribution
Access to sailboats, powerboats, and kayaks
Opportunity to travel on international sailing expeditions
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.
Based in St. Petersburg, FL, SailFuture serves 200 children and families a year through innovative programs ranging from international sailing expeditions to an entrepreneurship high school.
Dean of Students
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