Chief Impact Officer

CHIEF IMPACT OFFICER

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. Currently, we connect over 1,000 people to jobs each year; however, our results don’t just end with employment. 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

About the Impact Team

The Impact Team is the heart and soul of Cara. It is this team that delivers our renowned workforce development program rooted in social emotional learning (“SEL”) and personal transformation. The work of the Impact Team is foundational to bringing individuals in need back to the dignity and productivity of employment. Through these efforts, families become stronger, relationships are healed, and communities become more vibrant because nothing gives you a positive outlook on life like a meaningful career. The team is comprised of life and career coaches, trainers specializing in SEL, and specialists in supportive services, financial and digital literacy, program recruitment and intake.

About the Role

The Chief Impact Officer (CIO) serves as a member of the Executive Team and is responsible for overseeing the delivery of all Cara Collective programming, including recruitment and admissions, social emotional development, career coaching and advancement, and holistic participant support services. The Chief Impact Officer strategically manages Cara’s core program and initiatives related to our participants’ preparation for, placement into, and long-term success in employment. This role, and the team it leads, are the backbone of the organization. In addition to overseeing direct service delivery, the Chief Impact Officer manages and maintains program-connected external and internal stakeholder relationships.

As an Executive Team member, the Chief Impact Officer ensures the integration and alignment of program services between departments across the organization. This role provides unique insights on approaches to participant personal development and transformation, as well as career pathway development. The CIO will ensure programmatic alignment with employer and market demands utilizing data-based decision-making while collaborating with organizational leaders across operations, finance, external affairs, HR and other existing and future business units including our social enterprise Cleanslate. Additionally, the Chief Impact Officer should demonstrate consistent work ethic, a positive attitude, and a commitment to teamwork while upholding Cara’s mission and values at all times.

The ideal candidate is a proactive and influential leader who builds trust quickly, communicates with clarity, and partners effectively across all levels of the organization. They are known for driving results, navigating complexity, and delivering high-quality work that strengthens people and operations. They demonstrate strategic leadership and expansive thinking that supports and honors past practices with an eye towards trends and future innovations. They have significant, strong knowledge of and experience with leading organizations or teams through change.

The ideal candidate is self-aware and possesses a growth mindset. They approach challenges with curiosity, and lead with both empathy and accountability. They are passionate about serving the underserved and creating opportunities for them to thrive. They are committed to both leading a team and being a member of a team. They professionally develop staff, set high expectations for them, and strive to crush goals while keeping participant success top of mind. They are a leader who demonstrates significant experience in the C‑Suite with a history of strong accomplishments in organizations with comparable participant‑facing missions.

Reports to:

Chief Executive Officer

Direct Reports:

Team of Directors and Senior Manager(s), who oversee managers and front‑line staff for a total of 35+ Impact Team members.

Key Responsibilities

The Chief Impact Officer is a multi‑faceted high‑profile role with responsibility for a wide variety of programmatic matters, from operations to partnerships with employers, donors, and external stakeholders. Core focus areas include:

Program Execution and Oversight

• Lead and ensure proper execution of the complete spectrum of Cara’s proprietary direct service delivery model: recruitment/intake, social emotional learning, mental health and wellness, life coaching/supportive services, career coaching, and job placement/employment services.
• Ensure integration of additional services including, but not limited to, financial and digital literacy, and other topical content as deemed necessary for participant success and well‑being.
• Collaborate across all organizational domains to ensure operational, contractual, financial, and legal compliance with protocols, policies, and procedures whether internal or external to Cara.
• Partner with the external affairs team for fundraising, development, funding and implementation of innovative initiatives
• Ensure integration with existing and future social enterprise ventures (Cleanslate and Clear Space)
• Effectively deliver program services within Cara’s operational budget

Strategic Leadership

• Contribute to organization‑wide decision‑making and leadership as member of the Executive Team
• Shape, implement, develop and iterate programmatic elements of enterprise strategic plan
• Critical insights and support for organization‑wide policymaking, protocols, and processes

Continuous Improvement

• Research, study, and apply societal, macroeconomic, and industry trends to inform and innovate on our programmatic interventions and approach—refining and improving the curriculum and service delivery model where necessary to benefit participant outcomes.
• Develop and implement practices that routinely assess programmatic efficacy and efficiency, measure outcomes, and gauge participant satisfaction. Identify challenges. Create responsive solutions that inform program design and iteration.

Relationship Management

• Maintain and expand partnerships/resources that support the myriad and diverse needs of program participants (e.g. childcare, housing and food security, and/or substance abuse recovery).
• Effectively engage board members, and serve as staff to relevant committees of the board to share and gain insight on strategic direction, outcomes data, programmatic opportunities, impacts, and successes.
• Support all levels of donor engagement, where needed, with existing and prospective funders from initial application to post‑award updates/reports/presentations.
• Ensure meaningful corporate volunteer engagement that is consistently aligned with our programmatic instruction, particularly in career preparation, mock interviews, labor market knowledge, workplace comportment, and overall professionalism.

Staff Management & Development

• Coach, support, and develop program staff in accordance with industry trends, best and promising practices.
• Establish high‑performance standards and accountability.
• Foster and encourage on‑going professional development for all team members.
• Audit staff performance, providing continuous feedback, guidance and direction for improvement where needed.
• Collaboratively establish team goals and monitor progress, and set individual team member goals with direct reports.

Minimum qualifications:

• Progressive experience as an executive leader of direct service organizations with demonstrated success, preferably in a nonprofit focused on education, adult education, workforce development or social enterprise.
• Applicant may demonstrate expertise in one of two ways:
  • Graduation from an accredited college or university with a Master’s degree preferably in Social/Behavioral Sciences, Business Management, Public Administration) or a related field, PLUS a minimum of ten (10) years of direct service program experience; OR
  • A combination of 15 years of direct service program experience, training and education in relevant disciplines such as workforce development, social work, education, or adult education.

Knowledge, Skills and Abilities

• Experience leading, developing, and growing direct service programming to successful outcomes while utilizing data to drive improvements and participant outcomes.
• An established professional track record of developing and motivating others, acting with integrity, thinking strategically, and driving results within a positive workplace culture.
• Significant experience developing and maintaining relationships with employers other external partners
• Excellent written and verbal communication
• High accountability; high attention to detail; and the ability to manage multiple tasks in a fast‑paced environment.
• A passion for creating a diverse, equitable, and inclusive work environment and society.
• The ability to identify errors or irregularities and take timely appropriate action.
• The ability to demonstrate tact and diplomacy in managing employee and other stakeholder issues in a wide range of diverse situations.
• The ability to institute problem solving techniques in diverse and sometimes emotional situations with participants.
• Proficiency with CRM systems such as Salesforce.
• Ability to complete all required reports, documentation and assigned tasks in a timely fashion and in accordance with expected deadlines
• Ability to complete other duties as assigned, or as may arise.
• Experience leading a departmental or domain budget.
• A collaborative spirit and ability to work well with all stakeholders from board members to participants, funders to employers, staff to executive leadership, community to corporate partners.

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.

Why Join Us:

• Make an Impact : Help us shape the future of our city and our nation to be more inclusive and accessible to all.
• Growth Opportunities : We’re a growing organization that’s committed to developing both our staff and the people we serve. You’ll have the chance to shape your role and grow professionally.
• Community-Driven Environment : We pride ourselves on being a supportive, team‑oriented organization where community – with one another and the people we serve – comes first.

Starting Pay Range

We take budget and starting salary very seriously. We benchmark our roles to the market to offer competitive, market‑based compensation to all employees.

The expected starting pay for this role is $200,000 annually.

Benefits

• 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 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. To be considered for this role, be sure to submit a resume and tailored cover letter. 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 View email address on click.appcast.io.