Human Resources Assistant Jobs in Chicago, IL
Human Resources Assistant jobs in Chicago are in steady demand across healthcare, finance, and professional services, with hiring concentrated in the Loop, River North, and Streeterville. Employers actively filling roles right now include Midwest Express Clinic, ADM, and KOOTH. Scan the live roles below and apply to whichever ones fit.
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Job Title: People Operations Generalist (HR Generalist)
About Remarcable
Remarcable builds the software that keeps trade contractors' crews equipped and on schedule. Our platform brings material procurement, inventory and tool tracking, prefab requisitions and invoice automation into one place, connecting field crews, warehouses, purchasing teams and suppliers in real time. We were founded by former foremen, purchasers, project managers and engineers who lived the jobsite pain we now solve, and today we serve more than 40% of the top 50 electrical contractors in the U.S.
Backed by a $15M Series A led by Insight Partners (June 2025), we are growing fast across our teams in the U.S. and Vancouver, B.C. That growth is why we are hiring for this role.
The role
As our People Operations Generalist (HR Generalist), you will keep Remarcable's HR engine running smoothly as we scale. You will own the day-to-day operations of HR, primarily in our U.S. locations: Rippling HRIS and data, onboarding and offboarding, benefits and payroll inputs, compliance and policy. You will report to the VP, People and join a small, close-knit People team: one colleague in the U.S. (soon to be two) and two in Vancouver, B.C. With a team this size, no task is too small and no project is someone else's job.
One day you may run a benefits enrollment or audit HRIS data; the next you may onboard a cohort of new hires, document a process, or help create training. You will build the scalable processes, systems and documentation that let Remarcable grow without losing what makes it a great place to work. You will primarily support our U.S. employees and work closely with our Vancouver-based People colleagues.
What you'll do
HR operations, systems and data
Own the Rippling HRIS as the system of record: data entry, audits, workflows, permissions and integrations with payroll and benefits.
Process all employee lifecycle transactions accurately: new hires, job and pay changes, transfers, leaves and terminations.
Build and maintain HR reporting: headcount, turnover, time to hire, compensation and engagement metrics.
Document HR processes, build templates and checklists, and create self-serve resources for employees and managers.
Evaluate, implement and improve HR tools as we scale, and automate manual work where possible.
Employee support and relations
Be the first point of contact for HR questions from employees and managers across Marketing, Sales, Customer Success, Engineering, Product and G&A.
Guide managers on policies, documentation and HR processes, and support performance conversations.
Lead employee relations matters end to end: intake, investigation, documentation and resolution, escalating to the VP, People or People Business Partner as needed.
Talent acquisition and onboarding
Partner with our Recruiting team and U.S. hiring managers on workforce plans, job descriptions, interview processes and offers.
Own a consistent, welcoming onboarding experience for U.S. new hires, including remote employees across multiple states.
Manage offboarding, exit interviews and related documentation.
Performance, growth and engagement
Run performance review, goal-setting and promotion cycles; help managers calibrate fairly.
Support learning and development programs, career frameworks and manager training.
Run engagement surveys, turn results into action plans, and help shape culture, recognition and team events.
Total rewards
Administer benefits enrollment, renewals and employee questions for U.S. plans, working with brokers and carriers.
Support compensation work: salary benchmarking, merit cycles, equity communication and leveling.
Partner with Finance and Payroll on accurate, on-time payroll inputs, leaves and changes for U.S. employees.
Compliance and policy
Keep policies, handbooks and practices compliant with U.S. federal, state and local law, including for multi-state remote employees, and align with the Vancouver team on company-wide policies.
Manage leaves of absence, accommodations, I-9s and required filings and postings.
Draft and update policies as the company grows, and train managers on them.
Projects that help us scale
Lead or support People projects such as new-market or new-state expansion, HR tech rollouts, org changes and integration of new teams.
Bring ideas, raise risks and pitch in wherever the team needs it.
What you bring
Required
3–5 years of HR experience, including at least 2 years in a generalist or People Operations role.
Experience at a high-growth startup or scale-up, ideally in SaaS or technology.
Experience with Rippling HRIS and/or Payroll
Solid working knowledge of U.S. employment law, including multi-state compliance for remote employees.
Proven judgment handling employee relations, investigations and confidential matters.
Hands-on experience administering an HRIS (e.g., Rippling, BambooHR, HiBob, Workday), strong Excel or Google Sheets skills, and sharp attention to detail with HR data.
Strong communication skills and sound judgment when advising managers on policy and process.
A builder's mindset: comfortable with ambiguity, quick to create structure, and happy to do both strategic and tactical work.
Nice to have
Experience supporting employees in Canada, especially B.C. Employment Standards, or managing a cross-border workforce.
Experience with benefits renewals, compensation cycles or equity programs.
Familiarity with construction, trades or field-based industries, or supporting go-to-market and implementation teams.
HR certification such as SHRM-CP/SCP, PHR/SPHR or CPHR.
What success looks like
First 30 days: Know our product, customers and team; meet every people leader; learn our HRIS, policies and open employee matters.
First 60 days: Own day-to-day HR support for U.S. groups; run onboarding for new hires; flag the top 3 process gaps.
First 90 days: Lead at least one improvement project (e.g., onboarding, HRIS cleanup or policy refresh); core HR processes are documented and HRIS data is clean.
First year: Run a full performance or compensation cycle; deliver regular people metrics; help scale U.S. headcount smoothly.
Why Join Us
Opportunity to shape HR systems and processes as the company scales
Chance to start with a high-growth company at an early stage and advance as the company scales
Work closely with members of the People team on meaningful initiatives
Competitive salary and performance-based bonus
Comprehensive health and wellness benefits including Medical, Dental, Vision, STD, LTD and Life Insurance. 401(k) with company match.
Opportunity to grow with a fast-scaling tech company
Collaborative, mission-driven culture
Join Us
Apply now to help us build the future of procurement for the trades.
Please be aware of potential phishing scams. Remarcable will never advance job applicants money or ask them to send money (via Venmo, Zelle, Paypal etc.) to preferred vendors. If you are concerned about the application process, please contact Remarcable directly at (216)770-3322.
Remarcable is not associated with info-remarcable.com. For information about applying for a position with Remarcable, please reference remarcable.com.
Compensation Range: $70K - $85K
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Human Resources Assistant Jobs in Chicago: Frequently Asked Questions
How do I get a human resources assistant job in Chicago?
Focus your search on Chicago's Loop and River North business districts, where corporate headquarters and professional services firms post the most openings. Healthcare systems anchored in Streeterville and the Medical District also hire consistently. Candidates who combine a human resources degree or certificate with hands-on experience in HRIS platforms like Workday or ADP tend to move faster through hiring processes here. Tailoring your resume to specific industries matters in Chicago's competitive market.
Which companies hire human resources assistants in Chicago?
Companies currently hiring human resources assistants in Chicago include Midwest Express Clinic, ADM, and KOOTH, per current listings on Migrate Mate as of October 2026. Chicago's mix of Fortune 500 headquarters, large hospital networks, and regional professional services firms makes it one of the more active markets for this role in the Midwest.
Are there remote human resources assistant jobs in Chicago?
Yes, though availability is limited since human resources assistants often support in-person onboarding, filing, and employee interactions that require an office presence. About 81% of human resources assistant openings tied to Chicago are remote or hybrid as of October 2026, with most flexibility found in benefits administration and HRIS data entry roles rather than generalist or onboarding-focused positions.
How can I get a human resources assistant job in Chicago with little or no experience?
The most realistic entry path in Chicago is landing a coordinator or administrative support role at a staffing agency or mid-size company in the Loop, where turnover creates consistent openings for candidates without full HR experience. Chicago's large hospital systems, including those tied to Northwestern and Rush, also hire HR support staff at the entry level. A SHRM-CP or PHR exam enrollment, even while job searching, signals commitment to local hiring managers.
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