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Director Remote People Operations Jobs in Chicago, IL

Casechek

People Operations Manager

Chicago, IL · On-site +1

As a People Operations Manager , you will take full ownership of our people operations function. In ... Casechek is based out of Chicago's Fulton Market, but we're a hybrid, remote and in-person team.

Caresyntax

Key Account Director

Chicago, IL · On-site +1

Key Account Director Remote US / Chicago-base preferred About Caresyntax Caresyntax is a global ... Collaborate with Clinical Operations, Data Science, Statistics, and Regulatory teams to ensure ...

Caresyntax

Key Account Director

Chicago, IL · Remote

Key Account Director Remote US / Chicago-base preferred About Caresyntax Caresyntax is a global ... Collaborate with Clinical Operations, Data Science, Statistics, and Regulatory teams to ensure ...

Prelim

Business Operations Lead

Chicago, IL · Remote

$240K - $260K/yr

You'll collaborate with People Operations on software contracts, offsites, and team meetups. What ... Additional benefits include unlimited PTO, a remote work stipend, a life-style stipend, and twice ...

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All JobsPeople Operations JobsDirector Remote People Operations JobsDirector Remote People Operations Jobs in Chicago, IL

Director Remote People Operations information

See Chicago, IL salary details

$35K

$110.9K

$184.9K

How much do director remote people operations jobs pay per year?

As of Sep 6, 2026, the average yearly pay for director remote people operations in Chicago, IL is $110,926.00, according to ZipRecruiter salary data. Most workers in this role earn between $77,800.00 and $139,600.00 per year, depending on experience, location, and employer.

What does a director of remote people operations do?

A Director of Remote People Operations oversees the strategies and processes that manage remote employees within an organization. Their responsibilities typically include designing remote work policies, supporting virtual team engagement, ensuring compliance with labor laws across different locations, and developing programs for remote employee onboarding, development, and retention. They play a crucial role in creating a positive remote work culture and ensuring that remote employees have the tools and support they need to succeed.

How does a director of remote people operations ensure effective team engagement and communication across distributed teams?

A Director of Remote People Operations typically fosters team engagement and communication by implementing digital collaboration tools, setting clear expectations for regular check-ins, and promoting a culture of transparency. They often coordinate virtual events, manage asynchronous workflows, and provide training for managers on remote leadership best practices. Ensuring consistent feedback loops and recognizing employee achievements are also key strategies. Their role involves closely collaborating with HR, IT, and departmental leaders to optimize the remote work experience and maintain strong team cohesion.

What are the key skills and qualifications needed to thrive as a director of remote people operations, and why are they important?

To thrive as a Director of Remote People Operations, you need a strong background in HR management, remote workforce strategy, and employment law, typically backed by a degree in HR or business and relevant experience. Familiarity with HRIS platforms, remote collaboration tools like Slack or Zoom, and certifications such as SHRM-SCP or PHR are highly valuable. Exceptional communication, change management, and cultural sensitivity set top candidates apart by fostering trust and engagement in virtual teams. These skills are vital for building effective policies, maintaining compliance, and ensuring a positive employee experience across distributed environments.

What is the difference between Director Remote People Operations vs HR Director?

AspectDirector Remote People OperationsHR Director
CredentialsHR certifications, leadership experienceHR certifications, senior HR experience
Work EnvironmentRemote, cross-functional teamsTypically office-based, some remote options
Industry UsageTech, startups, remote-first companiesCorporate, large organizations, various industries
FocusRemote workforce management, talent strategyEmployee relations, compliance, HR policies

The main difference is that the Director Remote People Operations focuses on managing remote teams and implementing remote work strategies, while the HR Director oversees overall human resources functions within an organization, often in a traditional office setting. Both roles require HR expertise and leadership skills but differ in scope and work environment.

What are the most commonly searched types of Remote People Operations jobs in Chicago, IL?

The most popular types of Remote People Operations jobs in Chicago, IL are:

What are popular job titles related to Director Remote People Operations jobs in Chicago, IL?

For Director Remote People Operations jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Director Remote People Operations jobs in Chicago, IL look for?

The top searched job categories for Director Remote People Operations jobs in Chicago, IL are:

Director Remote People Operations jobs near you

People Operations Manager

Casechek

Chicago, IL • On-site, Remote

Full-time

Medical, Dental, Retirement, PTO

Re-posted 15 days ago

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.

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