Director of People & Culture

DIRECTOR OF PEOPLE & CULTURE

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 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 www.caracollective.org.

About the Cara Collective HR Team

The Human Resources (HR) Team is committed to serving, supporting and guiding the Cara Collective community in all aspects of HR. The HR Team is the link between Cara Collective’s employees and business entities, ensuring a community-driven organizational culture, strong employee professional development, implementation of policies and practices that support employee well-being, and creating a foundation where the organization, the staff, and the mission flourish.

About the Role

As the Director of People & Culture, you will be the heart of driving our organization’s mission to fuel a national movement to eradicate relational and financial poverty through a culture that is inclusive, supportive and allows all employees to thrive. You’ll have the unique opportunity to shape the employee experience, foster a culture of belonging, and lead organizational development initiatives that empower our team to transform lives.

This role is ideal for an HR professional who brings experience in organizational development and a genuine desire to enhance the human side of our growing staff community. You’ll work closely with Cara Collective’s executive team, leadership and staff to cultivate a culture that is both innovative and supportive, guiding our people as we expand our impact. Your influence extends to key areas such as building Cara’s employee culture, developing leaders across the organization, promoting inclusive practices, facilitating cultural integration across our entities, ensuring compliance with employment regulations, and more.

You will have a comprehensive scope in this role, encompassing not only Cara but also its affiliated social enterprise, Cleanslate, and any future social enterprises. You will be uniquely positioned to implement people, culture and HR best practices across the entire organization, contributing to the overall success and sustainability of Cara Collective's mission.

Qualifications 

The ideal candidate is an experienced human resources leader aligned with Cara Collective’s mission to advance equity and break the cycle of poverty. You bring strong business acumen, sound judgment, and the ability to balance strategic thinking with hands-on execution in a dynamic, mission-driven environment.

You are a proactive and influential leader who builds trust quickly, communicates with clarity, and partners effectively across all levels of the organization.

You bring a growth mindset, approach challenges with curiosity, and lead with empathy and accountability. You are passionate about fostering inclusive, people-centered workplaces and developing leaders who reflect organizational values.

What You Bring:

• At least 5 years of experience as a senior leader of human resources and people & culture with demonstrated success, preferably in a nonprofit or social enterprise environment
• An established professional track record of developing and motivating others, acting with integrity, thinking strategically, and driving results within a positive workplace culture.
• High accountability for strict deadlines; high attention to detail; ability to manage multiple tasks in a fast-paced environment.
• A passion for creating a diverse, equitable, and inclusive work environment.
• Excellent communication skills and a collaborative mindset.
• Proficiency with HRIS systems.
• Strong knowledge in labor relations, compliance, and change management.
• A collaborative spirit and ability to work with senior leadership.

Key Responsibilities

People Operations & Talent Strategy (35%)

• Drive full cycle recruitment, onboarding, retention and succession planning initiatives for Cara and its social enterprise(s) to ensure the organization continues to attract and retain top talent.
• Oversee the company’s Career Pathing strategy and execution.
• Lead professional development, job and career training efforts for employees and managers.
• Oversee employee benefit programs, ensuring they remain a vital component of all that makes Cara Collective a desirable place to work.
• Oversee the organization’s semi-annual employee performance evaluation process, including managing the process and training leaders on how best to conduct them.
• Lead periodic salary analyses to ensure Cara Collective stays on target relative to market compensation.
• Administer employee surveys; develop key performance indicators and benchmarks to evaluate and manage organizational performance.

Leadership & Organizational Development (30%)

• Lead a total team of 4 individuals and provide coaching, mentorship and growth opportunities.
• Serve as a member of Cara Collective’s Leadership Team, and a strategic thought leader for organizational culture & development and people development.
• Collaborate with COO and the rest of Executive team on development and implementation of organizational strategic plans and programs.
• Oversee HR initiatives and projects in the context of Cara Collective’s strategic priorities.
• Serve as a trusted advisor and confidant to staff at all levels, offering guidance on professional development, conflict resolution, and organizational growth.

 Change Management & Culture (30%)

• Partner with leadership to support organizational change initiatives, guiding employees through transitions while maintaining morale and productivity.
• Cultivate a positive, inclusive, and collaborative workplace culture that aligns with our values and mission.
• Foster a growth mindset and champion innovation, helping teams adapt to new tools, systems, and ways of working.
• Advocate for a healthy work environment, offering creative solutions for team-building, mental health support, and professional development.

 Compliance & Policies (5%)

• Manage organizational compliance with federal, state and local legislation pertaining to all personnel matters; maintain knowledge of industry trends in this area. Make recommendations to executive management as necessary.
• Communicate with employees regarding changes in statutory regulations or the organization's personnel policies and procedures.

Reports To

Chief Operating Officer

Direct Reports

The Director of People & Culture manages a team of 3 HR professionals, including an HR Manager who supervises the HR Associate.

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 – to one another and the people we serve – comes first. 

Starting Pay Range

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

This position’s expected starting pay range is $105,000 - $115,000 annually.

Benefits

Ø Medical, Dental, Vision Plans

Ø Basic Life Insurance

Ø Long Term Disability

Ø Personal Technology Reimbursement

Ø 4 Weeks Paid Parental Leave

Ø Starting with 17 Vacation Days, 8 Sick Days, 14 Paid Holidays

 Employee Paid Benefits

Ø Pre-Tax Medical Flexible Spending Account

Ø Pre-Tax Dependent Care Account

Ø Pre-Tax Transit & Parking Options

Ø Supplemental Life and AD&D Insurance

Ø Short-Term Disability Insurance

Ø 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 HR@carachicago.org.