Director of People and Culture

Job Description

Job Description

Director of People & Culture

Location: Chicago, IL (60638)

Reporting To: Chief Operating Officer

Status: Full-Time | Exempt

Mission

Architect and execute a high-performance, people-first strategy that enables Continental Sales Lots 4 Less to grow with intention, without compromising on culture, purpose, or compliance.

Why This Role Exists

We’re hiring a Head of HR but not your typical one. The Director of People & Culture is a strategic builder, integrator, and cultural steward who will shape how we attract, retain, develop, and care for our people. As Continental Sales Lots 4 Less expands, our people operations must scale in alignment with our purpose.

This leader will be the connective tissue between strategy and execution designing systems that empower high performance while nurturing a culture where people feel valued and inspired. You’ll report directly to the COO and partner with leadership across the organization to influence everything from workforce planning to engagement, succession, DEI, and compliance.

Guided by the Four Tenets of Conscious Capitalism

• Higher Purpose: You help connect the “why” behind every hire, every policy, every conversation.
• Stakeholder Orientation: You see employees as internal customers—and retention as a key performance indicator.
• Conscious Leadership: You coach with clarity, lead with empathy, and hold yourself and others accountable.
• Conscious Culture: You are intentional about building a workplace where people thrive and feel deeply connected to their work.

Your Core Functions

Talent Acquisition & Workforce Planning

• Own the full-cycle recruiting process from workforce planning to onboarding.
• Implement values-based hiring using EOS tools.
• Build strategic pipelines of mission-aligned talent to support future growth.
• Standardize job descriptions and compensation bands for equity and clarity.

People Strategy & Team Member Experience

• Lead the design of the full team member lifecycle from onboarding to offboarding.
• Drive programs that promote engagement, performance, retention, and well-being
• Launch stay interviews, pulse surveys, and feedback loops to keep a real-time pulse on culture.
• Introduce equitable, scalable recognition systems and internal mobility pathways.

Leadership & Organizational Development

• Create systems to identify and grow leadership talent before business growth outpaces people’s readiness.
• Facilitate Quarterly Conversations, career mapping, and skills-based development strategies.
• Coach leaders using EOS tools such as LMA, Delegate & Elevate, and the People Analyzer.
• Align leadership behavior with measurable outcomes, accountability, and core values.

Culture Stewardship & Internal Communications

• Act as the culture champion across the organization ensuring alignment between purpose, values, and action.
• Develop internal communication strategies that keep employees informed, aligned, and inspired.
• Partner with leadership to foster an inclusive, psychologically safe environment.

Process, Policy & Compliance

• Own all HR operations, including documentation of processes and policy enforcement.
• Ensure compliance across multi-state jurisdictions; lead audits, investigations, and corrective actions as needed.
• Mitigate risk while maintaining humanity in policy and practice.

HR Systems & People Analytics

• Manage HRIS (or implement one, if needed) to ensure data integrity, compliance, and insight.
• Develop and manage a People Scorecard with real-time metrics on retention, engagement, and talent health.
• Use analytics to guide decisions, not just measure outcomes.

HR Compliance & Total Rewards

• Ensure all compensation and benefits programs are competitive, equitable, and aligned with business strategy.
• Oversee annual benefits open enrollment and vendor management for medical, dental, vision, life, and supplemental plans.
• Conduct periodic reviews of wage and compensation practices for internal equity and market competitiveness.
• Monitor and manage FLSA classifications, ADA accommodations, leave administration, and other compliance-related HR processes.
• Maintain documentation and training protocols to ensure labor law compliance across all locations.
• Partner with finance to support payroll accuracy and benefit deductions; support budgeting and forecasting for people-related costs.

Key Success Metrics (Initial Targets May Evolve)

• Team Member Retention Rate
• % of A-Players in the Right Seats
• Leadership Development Bench Readiness
• Completion of Quarterly Conversations and 30/60/90-day check-ins
• Compliance & audit readiness

What You Bring

• 7–10+ years of progressive HR/People leadership experience, preferably in high-growth or multi-location organizations
• Strong knowledge of labor laws, employment practices, and compliance requirements
• Proven experience designing and implementing systems for talent, engagement, and organizational growth
• HR certification (SHRM-CP/SCP, PHR/SPHR) preferred
• Fluent in people technology systems (HRIS, ATS, survey tools)
• Strategic, structured, and able to balance empathy with execution
• A natural collaborator with an ownership mindset nothing slips through

What Makes This Role Different

This is more than a Director of HR title; it's a seat at the table to help co-create the future of a purpose-driven, performance-minded business. You’ll help shape not just how we grow, but who we become as we do it. If you’re a builder who leads with heart and holds the bar high, we’d love to meet you.