Training Specialist - Bilingual

TRAINING SPECIALIST

The Training Specialist prepares Cara participants for long‑term career success by facilitating classroom‑based and experiential learning focused on workplace competencies, socio‑emotional skills, and professional readiness. Through structured, trauma‑informed training, participants build the confidence, communication skills, and accountability needed to secure and sustain employment.

A supportive, high‑expectation learning environment is created so participants can practice, reflect, and grow before job placement. By partnering with internal teams and external trainers, the Training Specialist ensures learning experiences are aligned with employment pathways—resulting in participants who are prepared to thrive in the workplace and advance toward economic stability.

The ideal candidate is a mission‑driven facilitator and educator who thrives in dynamic learning environments and is deeply committed to participant growth and transformation. They balance structure with empathy, are confident leading groups, and are energized by helping individuals build the skills and mindset needed for workplace success.

• Minimum of 3 years of demonstrated experience facilitating adult learning, workforce training, or group‑based education in community‑based or human services settings.
• Strong facilitation and classroom management skills, with the ability to engage diverse learners.
• Experience instructing or facilitating workshops with justice‑involved individuals, youth/young adults, and individuals impacted by substances and mental barriers.
• Experience delivering or supporting curriculum focused on workplace competencies, socio‑emotional learning, and professional development.
• Experience working with an economically disadvantaged and diverse population, ideally in a coaching capacity, specifically from Chicago‑area neighborhoods such as Englewood, West Englewood, Roseland, Humboldt Park, Austin, Austin Gresham, Greater Grand Crossing, North Lawndale, and West Garfield Park.
• Ability to assess participant learning and adapt facilitation strategies accordingly.
• Comfort collaborating with external trainers, employers, or partners to enhance participant learning experiences.
• Strong organizational, communication, and documentation skills.
• Commitment to equity‑centered, trauma‑informed, and strengths‑based practice.
• Strong work ethic and business acumen with ability to excel in a fast‑paced and collaborative environment.
• Ability to facilitate classroom activities with native Spanish‑speaking populations with proficiency, required.

Curriculum Facilitation & Participant Learning (70%)

• Facilitate classroom‑based and experiential curriculum focused on workplace competencies, socio‑emotional skills, interviewing techniques, and professional readiness.
• Create a supportive, accountable, and engaging learning environment that promotes participation, reflection, and skill‑building.
• Adapt facilitation approaches to meet participants’ learning styles, needs, and readiness levels.
• Consistently assess the effectiveness of curriculum and instructional methods and contribute ideas for continuous improvement.
• Support participants in practicing and applying skills through role‑plays, group activities, and real‑world scenarios.
• Maintain clear expectations and boundaries while modeling professional behavior and emotional regulation.

Training Program Support & Collaboration (15%)

• Collaborate with internal teams to align training content with employment pathways and participant goals.
• Coordinate with external logistics and preparation for training sessions and workshops.
• Participate in team meetings, case conferencing, and planning sessions to support participant success.

Documentation (10%)

• Observe and document participant engagement, growth, and challenges throughout the training period.
• Provide timely feedback and insights to program staff to support holistic participant support.
• Assist in tracking attendance, participation, and learning outcomes.

Continuous Improvement & Professional Practice (5%)

• Reflect on facilitation practice and incorporate feedback from peers and supervisors.
• Contribute to…