Youth Advisor/Instructor

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Published 3 days ago

Youth Advisor/Instructor, The Possible Project

BOSTON, MA (NOT remote)


Imagine supporting student entrepreneurs in an out-of-school setting as they explore their passions and inspiring creativity as they identify problems to solve and solutions that become business ideas.

Imagine walking into an Innovation Center - equipped with a Makerspace for student entrepreneurs to learn skills to design prototypes for their business ideas. 

Imagine engaging in project-based learning activities that place students as the leaders of their own learning through hands-on activities that push them to think critically and collaboratively with other student entrepreneurs.

Envision supporting students in Advisory experiences to reflect on their learning, identify areas for growth, and discover deeper insights about their identities, goals, and post-secondary pathways.

Imagine a supportive adult professional learning community that sparks your creativity, honors your experiences, and encourages collaboration and ongoing coaching.

The Possible Project (TPP) is seeking a Boston-based Youth Advisor/Instructor

to lead students through TPP's Entrepreneurship curriculum and engage students in targeted college-career readiness through our Pathways Advisory.

Youth Advisors/Instructor​s will teach groups of high school students in our after-school program, supported by STEAM experts or other skilled adults. Utilizing TPPs Entrepreneurship curriculum, instructors will facilitate students’ engagement in design-thinking, ideation, iteration, prototyping, and development of a business plan and product. Youth Advisors/Instructors​ will also facilitate a small group advisory where they will provide opportunities for students to reflect on their learning, identify post-secondary pathways, set goals, and compile an e-portfolio to share with external audiences. 

Youth Advisors/Instructor​s should expect to contribute ideas to TPPs program development and ongoing curriculum design. This role also requires flexible scheduling, since TPPs programming runs after-school and Mondays - Saturdays throughout the year.


  • Effectively engage learners in Entrepreneurship and Advisory learning experiences, including: developing a business idea, product, plan, and pitch to external stakeholders; and reflecting on progress towards TPPs SEL, identify, and college-career readiness competencies.
  • Cultivate a strong community within TPPs learning spaces, meaning: understand the science of learning and how to promote students’ belonging by establishing shared norms, relationships, and routines that create a safe and brave space to take risks.
  • Engage in planning sessions in collaboration with other Educator-Advisors and STEAM technician/makerspace manager to prepare for learning experiences and reflect on learning (to inform lessons and curriculum planning)
  • Engage in ongoing department specific and organization-wide professional learning, including: bi-weekly sessions with the Program Team, 1-1 coaching cycles with Program leaders.
  • Contribute to the design of TPPs next generation curriculum 
  • Support students in the development of their e-portfolio that documents their progress throughout their experience at TPP
  • Track and monitor student progress towards TPP’s core competencies 
  • Collect, analyze, and use student data to drive high quality student experiences and outcomes
  • Collaborate with the Development team to engage external volunteers in programmatic events
  • Effectively use TPP’s systems (SIS and LMS) to track, monitor, and update student information each semester 
  • Participate in weekly Eship / Advisory meetings 



  • Professional Experience: At least 3 years of experience working with high school students in either formal classrooms/schools or informal settings (for instance, youth development, camp counselor)
  • Instructional approaches: experience engaging youth from under-resourced communities in ways that are culturally-responsive, project-based, and competency-based, with attention to the whole-child, SEL and identity development, and building a strong culture and community
  • Content knowledge: Experience in 1 or more of the following:
  • Entrepreneurship: you have started and run a business
  • College-Career counseling (e.g.: FAFSA, college essays, college admissions’ processes, career exploration, resume writing and interviewing)
  • Business: you bring experience in a specific aspect of business, e.g.: Marketing, Sales, Finance
  • STEAM: science, technology, engineering, arts, and mathematics 
  • Demonstrate entrepreneurial spirit that inspires students to explore passions and dreams while providing the scaffolds or supports to actualize them 
  • Commitment to the success of every learner; have a growth mindset and self-awareness 
  • A courageous learner, design-thinker, problem-solver, and ignite these qualities in others
  • Create a growth-promoting culture that is brave and safe; effectively manage learning experiences 
  • Strong facilitation; you believe learning is an active process, and support learners in driving their learning 
  • Commitment to Diversity, Equity, and Inclusion
  • Embraces change and navigates multi-cultural spaces with openness and awareness 


Compensation & Benefits

The Possible Project offers a robust compensation and benefits package including high-quality health benefits and an employer contribution to your 401(k) plan. 

DEI Statement:

We believe every member of our team and student body deserves opportunities for growth, success and inclusion. We recognize that for many of our students, staff and communities, their life journeys run through oppressive structures and systems (e.g. classism, racism, sexism) — and that’s what makes our organizational culture and work so necessary and important.

We believe that diversity in perspective, backgrounds, ethnicities and lived experience is a strength, and from that strength, we can accomplish great things with the students we serve. Together as students, staff, organizations, communities, volunteers, and partners, we are intentional about creating safe spaces where all members can speak authentically and be themselves.

We are committed to Diversity, Inclusion, and Equity. As members of The Possible Project community, our progression along this ongoing journey raises thoughtful questions, reveals biases, and opens conversations. We celebrate one another and are unified in our commitment to young people, excellence, and innovation. This work is our shared responsibility and our opportunity to welcome all members who share in our mission and strive to provide pathways that further prepare students in achieving their desired success.


The Possible Project (TPP) is a multi-year, youth entrepreneurship program offering students exciting project-based experiences:

  • the creation and running of student-directed, passion-based ventures 
  • hands-on experiences within TPP Social Enterprises
  • work-based learning opportunities through internships and fellowships  
  • learning about and use of high-technology maker equipment, such as laser cutters, 3-D printers and clothing printers/presses
  • personalized college and/or career advising

The spirit of entrepreneurship grounds students’ experiences, igniting their passions, inspiring creativity, and providing opportunities to engage in design-thinking, problem-solving, and build self-efficacy. Throughout their TPP journey, high school students work with dedicated educators, advisors, peers, and field experts; earn stipends; design products and services in a state-of-the-art makerspace; attend pitch panels and marketplaces; build and apply essential skills, mindsets, and social capital; and explore the exciting opportunities that exist post-high school. Students have fun learning, growing and interacting with peers as they design their futures.  

TPP is in its second decade of operations, having served nearly 1000 students in the greater Boston area. The organization employs 30+ professionals with plans to grow significantly in Boston over the next 4 years, as well as other cities beyond 2025. TPP offers a strong professional development ethos, a fast-paced entrepreneurial culture, innovative curriculum & pedagogy, and a commitment to excellence and student impact. Importantly, TPP is highly committed to Diversity, Equity and Inclusion in everything we do. Currently in an expansion mode, TPP plans to open a 35,000 sq ft Boston Innovation Center serving 1000 students a year, launching in fall 2021. 

TPP is currently developing its next generation Program design and curriculum which includes a focus on project-based and competency-based learning, culturally responsive teaching practices, whole-child approaches, and a commitment to developing not only skills and mindsets, but also students’ social-emotional learning and identity. TPPs vision is a world where young people shape their own futures, and we seek educator-advisors to actualize this, contributing to an evolving model of transformative learning. 

Youth Advisor/Instructor, The Possible Project

BOSTON, MA (NOT remote)


Imagine supporting student entrepreneurs in an out-of-school setting as they explore their passions and inspiring creativity as they identify…

Details at a Glance

  • Time Commitment
    Full Time Schedule


Temporarily Remote
Work must be performed in or near Boston, MA
Associated Location
31 Heath St, Boston, MA 02130, USA

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