Training Specialist - Bilingual

TRAINING SPECIALIST About Cara Collective

Cara Collective seeks to fuel a courageous national movement to eradicate relational and financial poverty. Through our four entities – Cara, Cleanslate, and Cara Plus – we engage job seekers, employers, and other organizations across the country to break the cycle of poverty through the power and purpose of employment.

At present, we produce 1,000 jobs each year; however, our results don’t just end with employment. Today, we take the insights gained over the past 30 years to equip other organizations and employers with practices to help build a more inclusive economy. Learn more acollective.org.

Cara Collective’s Impact Team drives the heart of our mission—ensuring every participant has the tools, resources, and support needed to succeed in their employment journey. The team works across our enterprise to align strategy, training, engagement, and coaching practices that not only prepare participants for meaningful careers but also foster long‑term personal and professional growth. By integrating data, innovation, and lived experience, the Impact Team ensures Cara Collective continues to deliver measurable results while shaping best practices that influence the broader workforce development field.

Their work is central to advancing our vision of creating pathways out of poverty and building a more inclusive economy.

The Training Team sits at the heart of Cara Collective’s participant experience. The team delivers the core learning experience for participants, building workplace competencies, socio‑emotional skills, and professional readiness through structured, supportive training. Working in close partnership with internal teams, the Training Team ensures participants are prepared to secure, sustain, and succeed in employment while upholding our core values of equity, dignity, and accountability.

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.

This role creates a supportive, high‑expectation learning environment where 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. You balance structure with empathy, are confident leading groups, and are energized by helping individuals build the skills and mindset needed for success in the workplace.

You are adaptable, reflective, and collaborative, with the ability to manage classroom dynamics, respond to participant needs in real time, and partner closely with internal teams and external training providers.

• Aminimumof3yearsofdemonstrated 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/facilitatingworkshopswith justiceinvolvedindividuals,youth/young adults,and individualsimpactedby substances and mental barriers.
• Experience delivering or supporting curriculum focused on workplace competencies, socio‑emotional learning, and professional development.
• Experience workingwithan economicallydisadvantagedanddiverse population,ideallyinacoachingcapacity, 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.
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