Program Management
MA - Boston metropolitan area
About the Organization

For the past seven years, The Possible Project (TPP) has designed, implemented, assessed, and refined a model for after school programming that provides high school students with an opportunity to: a) create and take products to market, b) partner with local businesses for real-work design and business operations projects, c) provide students with access to industry and professional mentors who can help hone their skills and grow their access to networks of supportive adults, and d) provide pathways counseling for post-secondary opportunities.

Through TPP's program, students have access to dream up, design, and create real products for sale in the cutting-edge Makerspace and learn job-readiness skills working in TPP's existing businesses: Made Possible and We Sell Possible.

TPP's impact stretches beyond the skills learned by the students who participate; using entrepreneurship as a mechanism for bolstering creativity, fostering perseverance, harnessing optimism, and revealing the possible. The Possible Project places importance on diverse perspectives and understands that they are critical to its success, and as such, values these perspectives in hiring and decision-making. To learn more about The Possible Project, please visit

About the Position

The Chief Learning Officer serves as the organization's senior leader of curriculum and pedagogy. The Chief Learning Officer will lead the development and refinement of TPP's approach to curriculum and instruction for its students and will oversee TPP's Entrepreneurship program. The Chief Learning Officer will also contribute to the pedagogy and curriculum evolution of TPP's Social Enterprises and Pathways programs, ensuring a high quality, meaningful, and impactful student experience for all program participants. The Possible Project is committed to educating students through the principles of social emotional learning and design thinking, developing culturally responsive and trauma-informed teaching methods that will prepare students to design their lives towards post-secondary and/or career success. Working closely with other members of the executive and education teams, the Chief Learning Officer will serve as an evangelist for the spread of TPP's programs to new schools and district partners, and the adoption of its approach to teaching social emotional learning, growth mindset, and job readiness skills by the education community at large. This is an exciting opportunity for a highly motivated and innovative leader to build upon the organization's current capabilities and elevate it to the next level of impact.

Reporting to the Executive Director, the Chief Learning Officer will serve on the executive leadership team and manage the Director of Education, and an overall team of eight. Primary responsibilities include:

Executive Leadership

  • As a member of the TPP executive team, contribute to the development and implementation of the overall organizational vision and strategy, ensuring that all departments and activities are well coordinated and lead to a compelling and impactful student experience
  • Contribute to TPP's ongoing commitment to cultural competency development and training
  • Serve as a mentor and role model for all team members, supporting a culture of learning, feedback, and continuous improvement
  • Collaborate with the Community Development, Social Enterprises, and Pathways teams, serving as a strong internal and external voice for TPP and its work, effectively communicating TPP's successes and value proposition to a variety of audiences, with the ultimate goal of accelerating impact
  • Play a major role in community and school development in relation to further expansion into Boston in the Fall of 2020, and identify opportunities for cross collaboration with current and prospective partner organizations
  • Drive the departmental budget development process and oversee ongoing reporting to ensure strong accountability
  • Work with the Vice President of Evaluation and Learning to publish papers and increase awareness of The Possible Project across the country, and thus, the organization's impact
  • Broaden TPP's access and exposure to leading thinkers and leaders within the education sector through networking and contributions at conferences/professional forums
  • In addition to sitting on the executive leadership team, the CLO will also serve as a member of the Program Project Team and Social Enterprises Project Team, helping to launch the new Innovation Center in the Fall of 2020

Instructional Leadership

  • Oversee the development, refinement, and streamlining of TPP's pedagogical approach, effectively introducing high school students to the principles of entrepreneurship, job-readiness, and/or post-secondary matriculation, as a way to ready young people from low income communities to actively participate as members of the 21st century workforce
  • Coach, mentor, and manage the education team, leading classroom observations and providing timely and relevant feedback, working closely with the VP of Human Resources to support staff professional development
  • Co-design and develop curricula, integrating research-based best practices based in social emotional and trauma-informed learning, as well as culturally responsive teaching, to create a cohesive program arc that supports the development of TPP's students
  • Facilitate trainings/workshops that can be used to prepare caring adults (with limited formal classroom teaching experience) to excel as teachers of content and mentors to high school students
  • Ensure effective refinement and implementation of TPP's model, supporting the development of hope, resilience, and growth mindsets in students, as well as its next generation educational model
  • Working hand in hand with the Social Enterprises and Pathways Department, drive student recruitment, retention, and realization at program sites; support students through program completion by ensuring all aspects of TPP programming are engaging for students and resources are in place
  • Collaborate and manage external partners including school-based personnel, community leaders, and other key stakeholders
  • Work with leadership team members in designing alumni programming, ensuring that consistency and excellence are at the forefront in all programmatic components
  • Partner with the Vice President of Evaluation and Learning to develop and implement data collection and measurement strategies, as well as identify/pilot evaluation opportunities to enhance program quality and student outcomes
  • Write and develop grants for continued organizational growth in partnership with the Vice President, Development and Partnerships
  • Collaborate with the Director of Communications and External Affairs to contribute to thought leadership in the spaces of social emotional learning, design thinking, and culturally responsive and trauma-informed teaching through articles, leadership presentations, and publications
  • Lead team members in the design and launch of a parent engagement program
Candidate Requirements:

Beliefs and Attitudes

  • A demonstrable passion for the mission, vision, and values of The Possible Project and a fundamental belief that all children can and will succeed if provided with opportunities, excellent instruction, and hands-on learning opportunities
  • Demonstrated commitment to diversity and inclusion, based on the communities they have served and the teams they have led
  • Enthusiasm for serving high school students in low income communities and working with creative colleagues from diverse backgrounds
  • Proactive attitude, upbeat personality, good sense of humor, and ability to thrive in a fast-paced environment
  • Driving passion for making a difference for the students TPP serves, with a longstanding commitment to trauma-informed and culturally responsive instruction

Experience and Credentials

  • 15+ years of relevant professional experience with progressively increasing responsibility, in education and/or youth development organizations, with a successful track record as a Principal, Chief Program Officer, VP Program, or VP Education, working within a relevant educational context (school or non-profit program) serving low income communities
  • Experience leveraging innovative approaches in student-directed and/or experiential learning techniques
  • Demonstrated success in visioning, creating, and executing programs in non-profit institutions or businesses, particularly start-ups
  • Direct experience managing educators and/or youth development staff delivering relevant programming, with a track record of preparing adults for roles in classrooms or other instructional environments
  • Track record of exceptional curriculum development and pedagogy delivery, aligned with the outputs of The Possible Project logic model
  • A Master's degree in education or a related area is preferred

Knowledge and Skills

  • Knowledge of culturally responsive instruction and a track record of developing and implementing culturally competent, trauma-informed educational programs
  • Strong evidence of rigorous use of data (quantitative and qualitative) to drive strategy and decision making
  • Experience managing teams to support student growth, both academically and in terms of soft skills such as hope and growth mindset
  • Ability to proactively deliver and solicit feedback on performance with an eye toward continuous improvement
  • Ability to work as part of a team, collaborating closely with high-powered leadership teams in a matrixed organization characterized by growth, change, and entrepreneurship
  • Strong communication skills, with an ability to communicate effectively with students, educators, community members, volunteers, and other key stakeholders
  • Excellent problem-solving, operational, and communication skills
  • Ability to implement strategy to develop staff of all levels, providing opportunities for growth for individuals and the organization

The Possible Project is an equal opportunity employer and does not discriminate on the basis of sex, race, color, religion, sexual orientation, national origin, cultural heritage, ancestry, political belief, age, marital status, pregnancy, physical or mental disability or veteran status.

Compensation and benefits:

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