People Operations Manager

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 on a mission to innovate the implant supply chain and bring greater transparency to the cost of patient care. From procurement to payment, Casechek automates workflows for vendor supported surgical procedures. Our emergent Bill Only solution provides a comprehensive system of record for Hospitals and Health Systems to manage the complexity of surgical cases with implantable medical devices, expose hidden expenses and surface revenue opportunities.

As a People Operations Manager, you will take full ownership of our people operations function. In this pivotal role, you will oversee all aspects of talent acquisition, workforce strategy, talent development and culture cultivation. As a trusted advisor to both leadership and team members, you will enhance policies and procedures, spearhead engagement initiatives, and manage compensation and benefits administration to support our team's growth and well‑being. This position offers a unique opportunity to lead and drive organizational growth.

Casechek is a highly collaborative environment, and our team is also self-motivated and works independently. We strongly believe that great ideas are not created in isolation. Our team interacts with our healthcare customers to understand their needs and ultimately deliver the best user experience possible.

About Us

• Casechek is based out of Chicago’s Fulton Market, but we’re a hybrid, remote and in-person team.
• We are highly motivated and passionate about solving healthcare’s messiest problems with new technologies.
• We value diversity, curiosity, and a passion for learning. The team has a lot of advanced degrees and even a few professional musicians.
• Innovating the implant supply chain is a marathon and not a sprint. We support each other in long-term growth and value developing transferable skills.

About You

• Highly motivated with a strong sense of urgency to drive results.
• Passionate about fostering great teams and building ethical organizations.
• Demonstrated ability to take ownership of projects with minimal oversight.
• Strong presentation skills, capable of articulating complex ideas effectively.
• Resourceful self-starter with a proactive approach to problem-solving.
• Exceptional ability to prioritize and manage multiple projects simultaneously.
• Proficient in handling highly sensitive and confidential information.
• Advocate for diversity and inclusion, committed to creating an inclusive work environment.

Responsibilities

• Lead all aspects of talent acquisition, from sourcing and interviewing to onboarding, ensuring a positive experience for candidates and team members.
• Develop and execute workforce strategies that align with organizational goals, fostering a culture of continuous improvement and employee engagement.
• Serve as a strategic advisor to leadership and team members on people operations matters, providing guidance and support.
• Oversee payroll and benefits administration in partnership with our PEO.
• Stay updated on HR best practices, labor laws, and industry trends to ensure compliance and drive continuous improvement.

Requirements

• 7+ years of People Operations experience including full-cycle recruiting, onboarding, payroll and benefits administration, policy development, personnel relations and leading engagement initiatives.
• Bachelor’s degree
• Experience filling technical and data driven roles including software engineering and data analytics positions.
• Strong analytical skills with the ability to use data to drive outcomes.
• Excellent interpersonal skills and coaching ability.
• In-depth knowledge of human resources best practices and labor laws.
• Demonstrated success in building high-caliber organizations.

Reside in the Chicagoland area and be able to work in the office as part of a hybrid work environment.

TECH STACK

• Leapsome
• Greenhouse ATS
• Google Workplace
• Slack
• Docusign
• Carta

WHY YOU’LL LOVE WORKING HERE

• Competitive Salary and Annual Bonus – The salary range for this role is $100,000 - $115,000
• Opportunity for Long-Term Incentives (LTI) – Be part of our success with equity or long-term incentive plans that grow with the company.
• 401(k) Match – Invest in your future with our generous matching program to help you build long-term financial security.
• Work-from-Home Flexibility – Enjoy the freedom to work where you're most productive with a supportive hybrid (Chicago) or remote setup (National).
• Flexible Time Off (Unlimited PTO) – Recharge and focus on what matters most with unlimited paid time off tailored to your needs.
• Parental Leave – Take time to bond and care for your growing family with fully paid parental leave options.
• Comprehensive Medical and Dental Benefits – Prioritize your health and well‑being with premium plans for you and your family.
• Brand-New Pro-Level Laptop – Equipped with top-tier tools and technology to set you up for success from day one.
• Annual Education Budget – Expand your skills and knowledge with dedicated funding for courses, certifications, and learning resources.