Employment Specialist 

About Cara Collective 

Cara Collective seeks to fuel a courageous national movement to eradicate relational and financial poverty. Through our three 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 www.caracollective.org.  

About the Cara Collectives Employment Services Team 

The Employment Services Team is responsible for securing job opportunities for participants and providing concierge-style service to our employment partners through job matching. 

We are a fast moving and passionate team with one focus, working with our job seekers to help them secure meaningful employment.  

About the Role 

Employment Specialists are monitored on key performance indicators including successful management of their participant caseload, consistent touchpoints with their caseload before being placed on a long-term job, send-outs, and send-out to placement conversion percentages with the ultimate goal being placements.   

Qualifications   

We are excited to offer this opportunity for a passionate individual to join our team and our community. This role is ideal for a proactive, relationship-focused professional eager to contribute to workforce development and help individuals secure meaningful, permanent employment. 

The ideal candidate will be inspired by Cara Collective's mission and committed to working in an environment dedicated to racial equity and breaking the cycle of poverty. They should be a self-starter, energized by fostering strong partnerships, highly organized with exceptional attention to detail, and committed to continuous learning. They should possess excellent interpersonal skills, a strong desire to collaborate as a team player, and approach challenges with a solutions-oriented mindset. They should excel in interacting with participants, demonstrating problem-solving skills to support successful employment placements. 

While prior experience in a social justice organization or with workforce development is not required, it is considered a plus. 

Requirements: 

• 1 -2 years of experience in workforce development, or a related field. 

• Strong organizational and written/verbal communication skills, with the ability to manage multiple priorities and meet tight deadlines. 

• Ability to work efficiently in a fast-paced, high-energy environment while balancing competing demands. 

• Adaptable and flexible in a changing environment. 

• Strong relationship-building skills with diverse stakeholders. 

• Proactive, hands-on self-starter with a commitment to operational excellence and continuous improvement. 

• Working knowledge of Microsoft Office Suite (especially Excel, Word, and Outlook) required; Salesforce experience preferred. 

• Ability to develop tools and templates to streamline and optimize operations. 

• Driven by Cara Collective’s mission and values, with a passion for supporting adults from all walks of life in advancing their lives and careers. 

• Demonstrated leadership qualities that foster trust, cultivate growth, and inspire others to see what is possible. 

• Solid educational foundation or equivalent professional experience that prepares you for success in the role. 

 This is a unique opportunity to contribute to Cara Collective’s transformative work while growing your career in workforce development. If you are ready to make an impact, we encourage you to apply! 

Key Responsibilities of the Position 

Participant Support (90%) 

• Manage a caseload of participants while providing assistance for all stages of the job search process including:   

• Application help  

• Interview prep  

• Post hire onboarding support    

• Consistent follow up and ongoing communication with participants and all internal teams.    

• Coach and guide participants to review job requirements and other employer expectations to determine best fit roles.   

• Participate in in person Cara Days where we get to know incoming job seekers.   

• Help participants navigate company websites in researching potential roles and companies to pursue (utilizing the Employer Research Sheet).   

Miscellaneous (10%) 

• Maintain accurate, timely, and complete data entry in Salesforce and other internal systems.  

• Track and manage monthly metrics related to job orders, send-outs, and placement outcomes.  

• Participate in monthly cross-departmental meetings with Coaching, Training, Recruitment/Admissions, and Employment Services teams to align on participant progress, employer needs, and shared goals.  

• Collaborate closely with internal teams to ensure a coordinated, participant-centered approach across the enterprise.  

Reports to 

Manger of Employment Services 

Direct Reports 

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 47,000- 52,000 

Benefits 

Cara Collective recently benchmarked benefits offerings and found that we exceed industry standards in terms of employee-friendliness and benefit offerings. Our comprehensive benefit package include: 

• Medical, Dental, Vision Plans 

• Basic Life Insurance  

• Long Term Disability  

• Personal Technology Reimbursement  

• 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 and inclusive work environment and is proud to be an equal opportunity employer. We do 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. This commitment applies to all employment practices, including those supported by technology or artificial intelligence tools used in the hiring process. 

We encourage individuals of all backgrounds to apply. If you are a qualified candidate with a disability and require reasonable accommodation to complete this application or participate in the interview process, please email us at kboelkens@carachicago.org.