People Operations Leader — Hybrid/Remote & Equity Options

Casechek; Chicago (IL); Hybrid; USD 100,000 - 115,000; Full time

Benefits offered by this job

Competitive salary & annual bonus

Long-Term Incentives (LTI)

401(k) match

Work-from-Home flexibility (hybrid/NC)

Unlimited PTO

Parental leave

Medical & dental benefits

Professional development budget

Company-provided laptop

Job summary

Casechek is seeking a People Operations Manager to own talent acquisition, workforce strategy, and culture initiatives. You will partner with leadership to shape policies, manage compensation and benefits with a PEO, and drive employee engagement in a hybrid environment.

The role requires 7+ years in People Operations, experience filling technical roles, and strong data-driven decision making. Chicago area hybrid/remote work options are supported.

Qualifications

• 7+ years in People Operations with full-cycle recruiting, onboarding, payroll and benefits.
• Experience building and scaling talent and culture in fast‑growing environments.
• Strong data‑driven decision making and policy development.
• Proven ability to lead engagement initiatives and coach leaders.

Responsibilities

• Lead all aspects of talent acquisition, from sourcing to onboarding.
• Develop workforce strategies aligned with company goals and culture.
• Advise leadership on people operations matters and compliance.
• Oversee payroll and benefits administration with our PEO partner.
• Stay current on HR laws and industry trends to drive improvements.

Skills

People Operations

Full-cycle recruiting

Onboarding

Payroll & benefits

Policy development

Employee relations

Engagement initiatives

Data-driven roles

Analytical skills

Interpersonal skills

HR compliance

Diversity & inclusion

Education

Bachelor's degree

Tools

Leapsome

Greenhouse ATS

Google Workspace

Slack

DocuSign

Carta

Job description

Casechek is seeking a People Operations Manager to own talent acquisition, workforce strategy, and culture initiatives. You will partner with leadership to shape policies, manage compensation and benefits with a PEO, and drive employee engagement in a hybrid environment.

The role requires 7+ years in People Operations, experience filling technical roles, and strong data-driven decision making. Chicago area hybrid/remote work options are supported.