Senior Community Strategy Specialist

Senior Community Strategy 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 35 years to equip other organizations and employers with practices to help build a more inclusive economy. Learn more at www.caracollective.org.

About the External Affairs Team

The External Affairs Department aims to advance Cara Collective’s mission by amplifying our brand, building strategic partnerships, attracting resources and investments, and driving public awareness and practice change. Through coordinated efforts across communications, development, and external engagement, the team ensures our message resonates with stakeholders and strengthens our impact. With a commitment to storytelling, relationship-building, and thought leadership, External Affairs connects Cara Collective to the broader community, fueling growth and deepening our influence in the workforce development field.

About the Role

Chicago’s current moment calls for urgent, coordinated action—and employment must be part of the solution. Cara Collective is working alongside community violence intervention (CVI) organizations, employers, and civic partners to expand access to economic opportunity for individuals most impacted by violence.

The Senior Community Strategy Specialist plays a critical role in the implementation and day-to-day execution of Cara Collective’s CVI Workforce Initiative. Reporting to the Senior Director of Community and Employment Strategies, this role is responsible for operationalizing partnerships once they are established, maintaining systems and relationships, and coordinating work across multiple teams and organizations.

Key Responsibilities

Initiative Implementation & Project Coordination (30%)

• Independently manage assigned CVI workstreams, ensuring timelines, deliverables, and next steps remain on track.
• Maintain systems and workflows that support day-to-day execution of the CVI workforce initiative.
• Coordinate internal and external meetings; prepare agendas, capture notes, and drive follow-up to completion.
• Track action items across teams and partners, proactively flagging risks, delays, or gaps.

Workforce & Employer Coordination (30%)

• Support senior director in collaboration with Cara Plus, Employment Services, and Business Development teams to align CVI participant pathways with employer, transitional job, and workforce opportunities.
• Support coordination for employer engagement activities, ensuring partners and internal teams have the information and materials needed to engage CVI participants effectively.
• Assist with planning and partner communication related to hiring events, workshops, and employer engagement initiatives.

CVI Partner & Ecosystem Engagement (20%)

• Maintain ongoing relationships with CVI partner organizations once pathways are co‑designed and launched.
• Participate in regular partner touchpoints (e.g., weekly calls) to ensure systems and processes are working smoothly.
• Coordinate communication between CVI partners and Cara internal teams to support participant needs and pathway execution.
• Support operationalization of shared processes including referrals, co-located cohorts, and other programming and associated preparation.
• Serve as a reliable, solutions-oriented‑ point of contact for partners navigating Cara systems and services.

Systems, Data & Infrastructure Support (20%)

• Help maintain internal tools, documentation, and tracking systems that support the CVI workforce initiative.
• Support basic data tracking, review, and analysis to inform continuous improvement.
• Identify operational challenges and improvement opportunities; escalate insights and recommendations to the director.
• Contribute to internal coordination related to infrastructure, model development, and training needs as they relate to CVI workstreams.

Qualifications

We’re excited to connect with candidates who bring a mix of operational excellence, relationship management, and commitment to economic and community safety.

Required & Preferred Experience

• 2–5 years of experience in workforce development, community partnerships, project coordination, or related field.
• Demonstrated ability to reliably execute a defined body of work with minimal supervision.
• Strong organizational and project management skills; able to manage multiple priorities and follow through consistently.
• Excellent collaboration and communication skills across internal teams and external partners.
• Familiarity with trauma informed, community based, or equity centered approaches preferred.
• Lived experience or deep proximity to communities most impacted by violence and economic exclusion strongly valued.
• Passion for equity, public safety, and expanding access to meaningful employment.

Reports To

Senior Director of Community & Employment Strategies

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. For this role, that means a minimum of three days in the office. 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 $57,000-$62,000 annually.  

Any offered salary is determined based on relevant factors such as applicant’s skills, job responsibilities, prior relevant experience, certain degrees and certifications and market considerations.  

Benefits

Cara Collective is proud to offer a comprehensive, competitive benefit package, with options designed to help you make the best decision for yourself, your family, and your lifestyle. Available benefits are based on eligibility.

• 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.