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Senior Director of Post-Secondary Pathways

We’re seeking an outstanding leader to serve as TPP’s Senior Director of Post-Secondary Pathways. The Senior Director will be responsible for leading our work to link students with compelling educational and employment opportunities aligned with their personal goals.

For the past seven years, The Possible Project (TPP) has built, 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) apply entrepreneurial and job-readiness skills to our in-house social enterprises, d) access industry and professional mentors who can help hone their skills and networks of supportive adults, and e) provide pathways counseling for post-secondary opportunities.

Through our program, students have access to dream up, design and create businesses that they are passionate about, while receiving direct and personalized support from our Pathways team. Ultimately, we aim to support our students in carrying their experiences and skills sharpened in our program, to dream up and design a plan for their lives.


As we think about our next five years and beyond, we seek a Senior Director to build on the strong foundation of college and career-readiness programming already in place at The Possible Project. As a key complement to our programming, all students participating in TPP have access to a college and career counselor. While our college pathways are robust, we are keen to identify and create additional resources for students seeking a direct pathway to a career. To this end, you will be responsible for expanding the internship, job placement and vocational resources available to students as complements to a rigorous college pathway which is available to any student who is interested in college attendance.

Your role will be to both supervise two college and career counselors while also working with groups of students directly. Through this work, you will monitor the quality of the counseling offered to students and make changes to the curriculum and techniques used to counsel students based on impact data and best practices learned from studies of organizations delivering similar programming.

Together, we will work to advance our goals in service of students and to partner with schools and communities to demonstrate what is possible through our core values of entrepreneurship, respect, teamwork, resilience, integrity, and fun.


As Senior Director you will be responsible for the following threads of work:

  • Team Management and Leadership
    • As a member of TPP’s senior leadership team, collaborate with our entire program team to continuously innovate our student experience, specifically ensuring that students develop agency in their post-secondary pursuits (with most thought leadership growth in the school-to-career expansion)
    • Serve as a mentor and leader for a team of counselors working directly with students to coach them through conceptualizing and taking action on a post-secondary path to success
    • Serve as an internal thought leader for post-secondary success and embrace a culture of continuous learning; we strive to be at all times an environment where we drive each other toward achieving common goals
  • Pathways Curriculum and Student Experience
    • In collaboration with current Pathways leaders, take a fresh look at our 3-year Pathways curriculum and use your deep experience to provide input on how we can grow our student experience and more fully realize our program outcomes
      • College Access and Persistence Frameworks
        • Using data from the field, help to grow student experiences in navigating, financing, and pursuing college
      • School to Career Frameworks
        • At TPP, we have come to understand that success in life can take many forms, as such we have seen a rise (especially in partnership with vocational schools) in students desiring to go straight to the workforce from High School. Using data from the field, help to grow student experiences in navigating and pursuing school-to-career options
        • Identify potential ways our school-to-career options could be amplified with the attainment of industry-recognized credentials
  • Partnership Management
    • College Readiness
      • Identify and cultivate key college access and college success partners to elevate our ability for students to access affordable routes to both 2 and 4-year colleges/universities
    • Career Readiness
      • Identify and cultivate key career access and career success partners that can support our expansion of students becoming career ready - this includes apprenticeship partners, internships, etc.
  • Direct Student Support
    • While you will have a team, being a model for our work is key to the success of your team. Work directly with students to support their paths to college by assisting with “right match” colleges; navigating applications, essays, and financial aid
    • Work directly with students choosing to enter careers directly from school, to identify career track first-time jobs, support resume building, and interview prep, while always building a plan with students to be “lifelong learners” helping them to see alternative paths toward industry-recognized credentials and degrees while working


There are innumerable ways to learn, grow and excel professionally. We know people gain skills through a variety of professional, personal, educational, and volunteer experiences. We respect this when we review applications and take a broad look at the experience of each applicant. We want to get to know you and the unique strengths you will bring the work. This said we are most likely to be interested in your candidacy if you can demonstrate the majority of the qualifications and experiences listed below:

  • 10 + years of experience working with students to achieve college and career goals
  • Experience leading a team of varying levels of experience
  • Experience and strong working knowledge of the following: Higher education (1-, 2-, and 4-year options); financing higher education; educational/career counseling; and positive youth development
  • Sensitivity to and understanding of the needs of young adults, particularly those who are low-income, recent immigrants, and/or face barriers to success; cultural competence is a must
  • Highly organized; ability to build systems
  • Data-driven and enjoys learning ways to improve work
  • Commitment to collaborate with a team and is energized to be a role model for staff and students
  • Commitment to live the values of our organization
    • Particularly as it relates to this work, data shows more and more that in college/career success, mindsets and “soft skills” matter. As such, it is important that leaders demonstrate a commitment to model what we believe lead to success for our students

In addition, the successful candidate will demonstrates the organization’s key values:








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


The Possible Project is working to close the skills and opportunities gap facing our students by providing resources and support that make them more likely to finish high school, complete education, and training beyond high school, and enter careers that will provide them with a living wage.

The Possible Project is a youth entrepreneurship program that teaches students with untapped potential on how to start and run their own businesses. In the process, students acquire a host of personal and professional skills that propel them to long-term success in life.

Through a combination of curriculum, support, and STEAM projects, students are empowered with the knowledge and skills necessary for success beyond high school—including resiliency, hope, and self-confidence.

The Possible Project is a 501(c)(3) organization. For more information, please visit possibleproject.org.

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.

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