Business & Entrepreneurship Program Manager

SailFuture
Saint Petersburg, FL


About the SailFuture Academy

The SailFuture Academy is a purposefully disruptive, private non-profit high school in St. Petersburg, Florida. Our mandate is to develop an exceptional model for system-involved youth and families experiencing extreme poverty.

We believe in making exceptional education accessible to hard to reach youth, and empowering our students to achieve economic freedom and social mobility through a pragmatic high school experience.

Students focus on foundational academic and character development curriculum in 8th - 10th grade and participate in an in-house internship in 11th grade and an external apprenticeship in their 12th-grade year.

Most notably, every student participates in a 7-week, international rite-of-passage sailing expedition onboard a 100’ school ship.

Entrepreneurship Instructor
At SailFuture Academy, our Business and Entrepreneurship curriculum forms the cornerstone of our educational approach. Our educational philosophy is rooted in a hands-on approach, encouraging students to experiment and create their own classroom business ventures to learn, act, and gain firsthand experience.

For instance, you may supervise a project in which students design, market, and sell t-shirts at a nearby middle school. Alternatively, you might organize a visit to a business where students perform a consultation, including a digital marketing strategy and brand redesign, or facilitate the cold calling of products made in a woodworking class.

Additionally, you will serve as a thesis advisor and educator for the senior class's business plan thesis projects, dedicating two classes each week to teach and guide students through the development of a polished business plan for a venture-backable product or service.

Our curriculum is crafted in-house, allowing you to collaborate closely with school leadership to develop, deliver, and implement the curriculum with significant creative freedom.

SailFuture Academy operates on a year-round, 5-term calendar with breaks between terms for students. Instructors work throughout the year, with designated weeks for planning and training during student breaks.

A typical workday runs from 8:00 am to 4:00 pm, with the aim of reducing after-hours work. Instructors benefit from dedicated annual planning and training time, along with weekly planning periods and allocated grading and planning time from 2:00 pm to 4:00 pm daily.

Responsibilities:

  • Work in partnership to co-author project-based learning curriculum and lesson plans

  • Lead up to 25 students in a classroom designed to teach critical thinking and problem-solving in a hands-on and project-based way

  • Lead a class of senior students to the successful completion of their business plan thesis

  • Ensure students uphold community standards in the classroom and within our community

  • Establish meaningful relationships and build trust with students and families to assist in improving their behavior, educational performance, and social relationships

  • Serve as the primary parent contact and campus advisory leader for students in your assigned ‘crew’

  • Submit daily professionalism score and assignment feedback for each student using provided rubric and guidelines

The Ideal Candidate:

The ideal candidate is aligned with our core values and is eager to begin, and capable of sustaining, the work needed to build a legacy project. The ideal candidate will:

  • Deep understanding of business and entrepreneurship

  • Lived or Professional experience that enables empathy for the kids we serve

  • Possesses a ‘whatever it takes’ mentality

  • 5+ years management or leadership experience

Compensation:

  • 7 weeks paid time off

  • 7 Paid Holidays

  • $250 per month employee health contribution

  • 401k with 6% match

Perks:

  • Membership to Clearwater Community Sailing Center (Kayaks, sailboats, beach)

  • Consistent time off throughout the year (1 week every 7 weeks)

  • 10-15 hours of planning time per week

  • (2) 1-week all expenses paid sailing experiences with faculty and students

  • Curriculum freedom and autonomy

Posted 2026-05-06

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