HR Generalist

Posted 4 Days Ago
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Chicago, IL, USA
In-Office
100K-115K Annually
Senior level
Artificial Intelligence • Insurance • Machine Learning • Real Estate
The Role
Manage day-to-day US People Operations: HRIS and data integrity (Rippling/HiBob), ticket queue, payroll and benefits administration, multi-state compliance and LOA management, onboarding/offboarding, reporting, and HR systems optimization to support rapid growth.
Summary Generated by Built In
Honeycomb

At Honeycomb, we're not just building technology, we’re reshaping the future of insurance. 

In 2025, Honeycomb was recognized by Dun & Bradstreet as “Top 10 Best Start Up Companies to Work For” in Israel and named by LinkedIn as “Top 10 Startups in Chicago”.

How did we earn these honors?

Honeycomb is a rapidly growing global startup, generously backed by top-tier investors and powered by an exceptional team of thinkers, builders, and problem-solvers. Dual-headquartered in Chicago and Tel Aviv (R&D center), and with 5 offices across the U.S., we are reinventing the commercial real estate insurance industry, an industry long overdue for disruption. Just as importantly, we ensure every employee feels deeply connected to our mission and one another.

With over $55B in insured assets, Honeycomb operates across 20+ major states, covering 60% of the U.S. population and increasing its coverage.

If you’re looking for a place where innovation is celebrated, culture actually means something, and smart people challenge you to be better every day - Honeycomb might be exactly what you’ve been looking for.


Position Summary

We’re hiring an HR Generalist to run the day-to-day operations and systems behind our People function for our US based employees. The work is hands-on and execution-heavy - payroll support, benefits administration, LOA management, multi-state compliance, HRIS, reporting, and the operational mechanics that keep a growing company running.

Reporting to the VP HR, you will partner closely with our Senior HRBP lead, who focuses on employee relations, performance management, talent density, and L&D programs. While you ensure the systems and operations behind the employee experience are consistent, compliant, and scalable.

Our U.S. team has more than doubled in the past year across 18 states, and we’re building a strong, scalable People foundation to support our growing workforce. We recently migrated to Rippling and have a lot of runway ahead to optimize it.

This hybrid role is based in our Chicago office three days a week (Tuesday through Thursday) with occasional Mondays as needed.

Key Responsibilities:

  • Day-to-Day People Operations

    • Maintain accurate employee data and records in the HR tech stack - process changes, audit fields, and keep the system trustworthy as the source of truth.
    • Handle the transactional ticket queue (pay questions, benefits enrollment, address and tax changes, verification requests, system access) with accuracy and quick turnaround

    Systems, Data & Rippling Maintenance

    • Work fluently across our HR stack: Rippling, HiBob, Google Workspace, Claude Enterprise, Culture Amp and Greenhouse 
    • Serve as the liaison between Rippling and our team - our in-house HRIS expert configuring, optimizing, and continuously improving the platform.
    • Drive data integrity across all HR systems through audits, clean-up, and disciplined data hygiene.
    • Build and maintain reporting and dashboards that give the People team and leadership reliable visibility into the workforce.

    Payroll, Benefits & Compliance

    • Provide payroll support, partnering with our Finance stakeholders to process end-to-end payroll.
    • Administer benefits end to end, including health plans, HSAs, 401(k) management, and COBRA, plus vendor and broker coordination. Run open enrollment and communicate and market benefits and systems updates to employees.
    • Partner with the HRBP and Payroll stakeholders to ensure Leave of Absence is handled end to end with accuracy and care. 
    • Own the multi-state compliance calendar (federal, state, and local) and keep us compliant in all states where we operate, maintaining audit-ready documentation, state-specific addenda, and required postings while surfacing risks before they become problems.

    U.S. Employment Lifecycle Operations

    • Execute pre-boarding, onboarding, and offboarding: system setup, paperwork, payroll and benefits enrollment, IT coordination, final pay, and data archival.
Qualifications & Experience
  • 5 - 7 years of progressive, hands-on People Operations experience, with significant time spent in a startup or high-growth company.
  • Direct experience owning payroll, benefits, and multi-state compliance, including vendor management (payroll providers, benefits brokers).
  • Hands-on knowledge of Rippling, Greenhouse, and Culture Amp is required, including administering, configuring, and optimizing these platforms. Comfort with Google Workspace, Slack, Monday, and Claude.
  • Strong understanding of U.S. HR operations best practices, benefits administration (COBRA, HSAs, 401(k)), and multi-state compliance and operational risk management.
  • You use AI tools to automate repetitive work, draft communications, summarize data, and accelerate everything from onboarding to compliance reporting.
  • Clear, accurate written communication across email, Slack, tickets, and documentation.
  • SHRM-CP, CPP, or similar certification is a plus but not required
Benefits
  • Salary Range: $100,000 - $115,000, plus a target 10% annual bonus
  • ISO stock options
  • Medical, dental, and vision coverage for you and your dependents
  • HSA with company contributions
  • 401(k) with employer match
  • Flexible time off 
  • 10 company-paid holidays
  • Paid family leave

Honeycomb is committed to fair and equitable compensation practices. The base salary range listed in each job posting represents our good faith estimate of what we expect to pay for the role. Actual compensation may vary based on skills, experience, education, and location, as well as internal alignment and market factors.


Skills Required

  • 5-7 years progressive People Operations experience in a startup or high-growth company
  • Direct experience owning payroll, benefits administration, and multi-state compliance, including vendor management
  • Hands-on knowledge administering, configuring, and optimizing Rippling, Greenhouse, and Culture Amp
  • Comfort with Google Workspace, Slack, Monday, and Claude Enterprise
  • Strong understanding of U.S. HR operations best practices, benefits administration (COBRA, HSAs, 401(k)), and multi-state compliance
  • Experience using AI tools to automate repetitive work, draft communications, and summarize data
  • Clear, accurate written communication across email, Slack, tickets, and documentation
  • Ability to work hybrid in Chicago office three days a week (Tuesday-Thursday)
  • SHRM-CP, CPP, or similar certification

Honeycomb Insurance Compensation & Benefits Highlights

The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Honeycomb Insurance and has not been reviewed or approved by Honeycomb Insurance.

  • Healthcare Strength Employees receive comprehensive medical, dental, and vision coverage, including 100% premium coverage for employees and additional support such as an HSA with company contributions.
  • Flexible Benefits A broad set of allowances and reimbursements is described, including a $600 annual perk allowance and support for home office setup plus monthly internet/phone/co-working reimbursements.
  • Equity Value & Accessibility Equity is positioned as a meaningful part of total rewards through stock options/RSUs with multi-year vesting, framed as valuable in a growth-stage company context.

Honeycomb Insurance Insights

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The Company
Chicago, Illinois
190 Employees
Year Founded: 2019

What We Do

Honeycomb was built to disrupt the real estate insurance industry. Using Artificial Intelligence and computer vision, we offer apartment buildings, condominium associations and single-family rental dwellings perfectly customized policies at unbeatable rates. Our digitally-native platform makes purchasing insurance an easy and transparent process for property owners, property managers associations directors, and retail agents.

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