LEADERSHIP COACH

Our Piece of the Pie; Hartford (CT); On-site; USD 42,000 - 56,000; Full time

Benefits offered by this job

Medical, dental, vision insurance

401(k) retirement plan with company-m匹

Life and disability insurance

PTO and paid holidays

Job summary

Our Piece of the Pie seeks Leadership Coaches to walk with each young person toward education, employment, and life goals. You will mentor, advocate, and practice CBT/TEB, ARS, TIC, and MHFA to empower resilience, self-efficacy, and belonging.

Responsibilities include building trust-based relationships, providing stabilization support, and coordinating ILPs and life-skills opportunities in community and school settings.

Qualifications

• Bachelor’s degree in social work, education, psychology, human services, or related field preferred — or equivalent experience.
• At least 2 years’ experience working with youth ages 14–24 in youth development, case management, or workforce development settings.
• Demonstrated ability to build trust and meaningful relationships with leaders from diverse backgrounds, especially those impacted by trauma, poverty, the justice system, or foster care.
• Familiarity with PYD, TEB, TIC, ARS, CBT, MHFA, Motivational Interviewing.
• Skilled in workshop facilitation, coaching, and managing individualized plans.

Responsibilities

• Build rich relationships through consistent, authentic engagement focused on each leader’s story and goals.
• Use trauma-informed approaches to sustain trust and create emotionally safe spaces.
• Provide stabilization support and barrier reduction (housing, food, transportation, documentation, clothing).
• Integrate emotional wellness and mindset coaching into daily interactions.
• Promote a sense of purpose, belonging, and motivation by identifying individual spark and values.
• Maintain regular communication and visibility in communities, including home and school visits.

Skills

Bachelor’s degree

Youth development experience

Trauma-informed care

Strong communication

Data tracking

Education

Bachelor’s degree

Job description

Description

Our Leadership Coaches are the heart of our mission—walking alongside each young person to build trust, foster belonging, and offer consistent support. This role is rooted in Positive Youth Development (PYD), healing-centered engagement, and belief in each young person’s capacity to define and pursue their own path forward.

The Coach is a mentor, advocate, and practitioner who empowers to build resilience, emotional regulation, and self-efficacy while working toward education, employment, and life goals. Using frameworks like CBT/TEB (Thoughts, Emotions & Behavior), ARS (Authenticity, Resilience, Safety), Trauma-Informed Care (TIC), and Mental Health First Aid (MHFA), YDCs support youth with individualized learning plans (ILPs), life skills, career exposure, and community-based opportunities that align with their identity, interests, and strengths.

Key Responsibilities

Youth Engagement, Stabilization & Trust-Building

• Build RICH relationships through consistent, authentic engagement that centers each leader’s story, goals, and lived experience to establish trust and connection as the foundation for growth.
• Sustain trust through trauma-informed approaches that model empathy, support self-determination, and create emotionally safe spaces.
• Provide stabilization support and barrier reduction (e.g., housing, food, transportation, documentation, clothing, crisis navigation).
• Integrate emotional wellness and mindset coaching practices (e.g., CBT, ARS, identity development) into daily interactions.
• Promote a sense of purpose, belonging, and motivation by helping to identify internal “spark” and values.
• Maintain regular communication and visibility in communities, including home and school visits.

Individualized Planning (GPS Coaching)

• Develop and maintain Individual Learning Plans (ILPs) using OPP’s GPS model: Goal setting, Pursuit, and Strategy.
• Use data from strength-based assessments to build leadership-centered, culturally responsive goals.
• Track and review progress on ILPs quarterly, including growth in the 6Cs.
• Align ILPs to stabilization needs, academic planning, employment readiness, and personal development.

Youth Development & Coaching

• Model authenticity, accountability, emotional regulation, and a growth mindset; create a safe, affirming space for leaders to thrive.
• Facilitate and/or coordinate workshops on life skills, PYD, digital literacy, career readiness, conflict resolution, and self-regulation.
• Coordinate service-learning projects and community-based opportunities based on readiness, interests, and aspirations.
• Support development in leadership, civic engagement, and advocacy skills through exposure and guided practice.
• Cultivate entrepreneurial learning experiences through partnership development and coordination.
• Ensure that coaches themselves are charged up, practicing reflection and emotional regulation to show up whole.

Education & Career Development

• Support with re-enrollment or re-engagement in school, GED programs, credit recovery, or alternative education.
• Collaborate with caregivers, teachers, and school staff to monitor attendance, progress, and academic goals.
• Coordinate post-secondary planning, including credentialing programs and college access.
• Deliver or coordinate Career Competency Development Training (CCDT).
• Assist in building resumes, completing applications, preparing for interviews, and securing jobs or internships.
• Transition leaders to OPP’s Pathways to Careers Initiative when developmentally ready.

Community Engagement, Family Partnership & Advocacy

• Serve as a visible OPP ambassador and advocate in community spaces and systems.
• Build and maintain partnerships with schools, social workers, probation officers, and other support systems.
• Attend court, DCF meetings, or case conferences to ensure access to second-chance opportunities.
• Conduct home visits and host caregiver meetings to engage families in success.
• Educate families on OPP’s mission, program model, and how to support leadership goals.

Documentation, Data & Accountability

• Maintain accurate and timely documentation in ETO or other data systems (ILPs, case notes, placement verification).
• Track outcomes across engagement, retention, stabilization, and 6C growth.
• Use data to inform coaching practice and ILP adjustments.
• Participate in weekly supervision, case conferencing, and internal training to sharpen tools and strategies.
• Collaborate with Directors to vet and build leadership-centered partnerships that align with mission and needs.

Requirements

• Bachelor’s degree in social work, education, psychology, human services, or related field preferred—or equivalent lived and professional experience.
• At least 2 years’ experience working with youth ages 14–24 in youth development, case management, or workforce development settings.
• Demonstrated ability to build trust and meaningful relationships with leaders from diverse backgrounds, especially those impacted by trauma, poverty, the justice system, or foster care.
• Familiarity and experience with PYD, TEB, TIC, ARS, CBT, MHFA, Motivational Interviewing.
• Skilled in workshop facilitation, coaching, and managing individualized plans.
• Strong documentation, case management, communication, and organizational skills.
• Experience with data tracking systems such as ETO preferred.
• Valid driver’s license, reliable transportation, and willingness to conduct community-based work.

We offer comprehensive medical, dental, and vision insurance, 401(k) retirement plan with a competitive company match, company-paid life and disability insurance, and generous paid time off (PTO) and paid company holidays.