Training Specialist - Chicago, IL

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 ...

Job description

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 at

About the Cara Collective Impact Team

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.

About the Cara Collective Training Team

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.

About the Role

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.

Qualifications 

The ideal candidateis 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.

Requirements

• A 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/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. 

Key Responsibilities

The purpose of this section is to outline the primary responsibilities of the position, providing a clear and structured overview of the role's expectations and duties within our organization.

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 externalgistics, and preparation for training sessions and workshops
• Participate in team meetings, case conferencing, and planning sessions to support participant success

Participant Progress & Do

•  training partners or guest facilitators to enhance learning experiences
• Support scheduling, lo

cumentation (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 the refinement of curriculum and training approaches
• Participate in professional development opportunities aligned with Cara's values and learning culture

All other responsibilities, as assigned 

Reports To

Manager of Training

Report (s) 

N/A

Workplace Type & Team Culture

Cara Collective has a strong team culture that values collaboration, communication, and camaraderie. We believe in the power of working together in person, which is why we expect our employees to be onsite at one of our Chicago-based locations multiple days each week.  The exact number of onsite days per week may vary by role, employee tenure, and other factors. This commitment to in-person collaboration fosters a sense of belonging and teamwork among our employees, creating a supportive and dynamic work environment.

We consistently measure staff satisfaction through employee surveys and have found that year over year, the vast majority of staff agree that Cara Collective is a great place to work and grow. This high level of employee satisfaction reflects our dedication to creating a positive and fulfilling workplace for all members of our team.

Starting Pay Range

We take budget and starting salary very seriously. We market our roles and are using a salary analysis tool called Payscale and offer competitive, market-based compensation to all employees.

This position's expected starting pay range is $52,000-55,000.

Benefits

Cara Collective recently benchmarked benefits offerings and found that we exceed industry standards in terms of employee-friendliness and benefit offerings. Employee out-of-pocket contributions are substantially lower, in some cases up to 63% less. Our comprehensive benefit package include:

• Medical, Dental, Vision Plans
• Basic Life Insurance
• Long Term Disability
• Personal Technology Reimbursement
• 4 Weeks Paid Parental Leave
• Starting with 17 Vacation Days, 8 Sick Days,
• 14 Paid Holidays

Employee Paid Benefits

• Pre-Tax Medical Flexible Spending Account
• Pre-Tax Dependent Care Account
• Pre-Tax Transit & Parking Options
• Supplemental Life and AD&D Insurance
• Short-Term Disability Insurance
• 401(k) Retirement Plan (employer match up to 4% upon hire & immediately vested)

As of this posting, we annually review our benefit offerings to meet our employees needs and be competitive in the market. All listed benefits offerings a at the discretion of the employer.

Equal Opportunity Employer

Cara Collective is committed to creating a diverse work environment and is proud to be an equal opportunity employer. Cara Collective does not discriminate on the basis of race, color, national origin, sex, gender identity, religion, sexual orientation, age, disability, parental status, veteran status, or any other protected status under applicable laws. We encourage individuals of all backgrounds to apply. If you are a qualified candidate with a disability, please email us at if you require reasonable accommodation to complete this application.