Deputy Director of Fellow Learning & Development


The Great Oaks Foundation is a non-profit organization that brings its model of high dosage tutoring to schools from Maryland to Connecticut with the mission of preparing students for college success. The tutoring is provided by the Great Oaks AmeriCorps Fellows, which is a selective cadre of recent college graduates who deliver high-dosage small group instruction. This is a crucial strategy to increase student achievement and build a pipeline of teachers to work in our schools. 


We recruit, train, and support a corps of tutor/mentors in a year-long fellowship in schools that embrace the power of high-dosage tutoring. Great Oaks Fellows focus on three tenets:

  • Our Fellows Instruct for Mastery through the provision of high dosage tutoring. Students must have deep knowledge, understanding, and the ability to apply that to new contexts and situations. Mastery emphasizes continuous learning.
  • Our Fellows Mentor for Leadership through providing site based social-emotional learning support. Our students will use the skills that they have learned to shape the world and not be defined by its current limitations. Leadership towards equity and justice is essential to the work we do in schools.
  • Our Fellows Develop Community through parent engagement, after school clubs, and presence throughout the school. Community is the basis for healthy development and for active engagement with the world. 

The Great Oaks Foundation has successfully replicated this program in Newark, NJ; Bridgeport, CT; New York, NY; and Wilmington, DE. Additionally, we have begun partnering our Fellow program with several non-Great Oaks schools as well. A select group of the Fellows are enrolled in a Teacher Residency program that is being conducted in partnership with NYU’s Online Teacher Residency Program and Relay Graduate School of Education.


As Great Oaks prepares for expansion, we are creating a new role to focus on the learning and development of the key site-based staff essential for an effective Fellowship program: Fellows, plus the various staff members who mentor and manage Fellows at each of our sites. In this position, you will support the arc of development for Fellows and staff members by designing and facilitating trainings that will support their own professional growth while maximizing their impact on students.

This role is part of the Great Oaks Foundation’s AmeriCorps Fellows team, reporting to the Director of Fellow Development.


As Deputy Director, you will:

  • Design and facilitate high-quality adult learning experiences focused on skill development, mindset development, and issues of diversity, equity, inclusion, and antiracism. The goal of these sessions is to engage Fellows and make the most out of our limited time to promote their growth and development. You should expect to design a mix of asynchronous, virtual experiences that Fellows can complete independently as well as live sessions to be facilitated in-person or virtually. In many cases, session materials currently exist but need to be updated or adapted to a virtual format. You will be part of a team of skilled facilitators, and we work together to determine who is best positioned to lead a particular learning experience.
  • Apply your knowledge of adult development by working in partnership with school site leadership to schedule Fellow learning sessions for the highest-leverage moments during the school year. This requires a deep understanding of adult learning and the development path of first-year educators, as well as strong relationship-building and lateral management skills. Our team is responsible for the growth of both Fellows’ technical skills and their mindset development. We are building an arc of development for Fellows and staff members, and we need your help to operationalize it.
  • Support the development of the staff members who mentor and manage Fellows at our sites. While the primary focus of your role is the development of Fellows, you should expect to support our team’s programming for Fellow Leads, Fellow Managers, and Fellow Directors at our sites. You will play a role in both design and facilitation here. As our program grows, your role may focus on supporting the staff members at a subset of sites. Depending on your location and skills, we will work together to determine division of responsibilities.
  • Maintain an accurate calendar of when, where, and how sessions are happening, and create an organization system for session materials. This can be a challenge given the size of our network and the different levels of support we provide to each site. You will need to ensure that we have accurate information on our internal calendars and that sites have reserved the same times for Fellows or staff members. Success in this area will ensure that our programming avoids potential conflicts and maximizes the availability of our team’s facilitators. With better knowledge management, we will avoid reinventing the wheel and we will ensure that staff members know how to access materials from their learning experiences.
  • Participate fully in the fast-paced work of the Great Oaks Foundation’s AmeriCorps Fellows team. We are a high-functioning team responsible for many projects throughout the year. Our team structure is very collaborative, and it’s common for the entire team to support each of these projects. Here is a partial and non-exhaustive list of what we do together:
    • Fellow pre-service retention and development, in partnership with the Great Oaks Recruitment Team
    • Major programming such as the Great Oaks Forum every August, Beyond the Corps Day every winter, and Alumni Induction at the end of the year
    • Check ins, progress monitoring, data analysis, and collaborative problem-solving with the leadership of each site’s Fellows program
    • AmeriCorps compliance, budgeting, and reporting
  • Contribute to the Great Oaks Academics Team on projects in service of the broader Great Oaks Model and vision. This includes, but is not limited, to the following key domains:
    • Building Great Oaks as an anti-racist organization with specific training and support for staff, Fellows, teachers, and leaders on these issues
    • Participating in staff conversations focused on diversity, equity, inclusion, and antiracism
    • Establishing a culture of adult learning
    • Supporting our Teacher Residency program by helping to identify and recruit Fellows who are interested in earning their certification
    • Strengthening our connections between the schools, Fellows and the communities we serve
    • Facilitating network-wide professional learning experiences 


  • Bachelor’s Degree
  • 4+ years of teaching experience, working directly with students from low-income backgrounds
  • Significant experience designing and facilitating adult learning experiences
  • Experience leading adults, through mentoring, coaching, facilitation, or direct supervision
  • Knowledge of adult learning theories and principles, and a passion for supporting early-career educators
  • Passion for academic learning and an insistence on academic excellence for all students
  • Excellent oral and written communication skills
  • Ability to share and receive constructive feedback with staff members that you support but don’t manage directly
  • Superb organizational and self-management skills, with an ability to handle multiple responsibilities effectively and thoughtfully
  • An attitude of doing whatever it takes to help all students achieve academic success, including a willingness to work occasionally on the weekend or in the evening
  • A strong belief that all students can succeed


  • Master’s Degree in teaching, education, or a related field
  • 6+ years of experience in schools
  • Coaching experience
  • Experience designing and facilitating sessions focused on diversity, equity, inclusion, and antiracism
  • AmeriCorps experience
  • Great Oaks Fellowship experience
  • Math instructional experience
  • Tutoring experience, via AmeriCorps or City Year or a similar program
  • Familiarity with Kim Marshall’s rubric for teacher evaluation


Great Oaks provides a competitive compensation and benefits package; exact compensation will vary based on experience and education. Must also have proof of U.S citizenship or legal resident status.

Location: The ideal candidate for this role lives in the Northeast Corridor, as this role requires frequent travel to schools located in Baltimore, Wilmington, Newark, New York and Bridgeport.

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