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Payroll & Benefits Specialist

| Chicago

We are EXPANDING our People Operations team at our Home Office in Chicago, IL and adding a People Operations/Payroll & Benefits Specialist.

Company Overview

Launched in 2014, ShipBob is a tech-enabled fulfillment and logistics solution for growing e-commerce companies. Our goal is to alleviate the daily stress associated with picking, packaging and shipping so business owners can focus on more important aspects of their brand. Through our software and operations arm, we are on a mission to help businesses be successful online

We pride ourselves on our inclusive and richly diverse company culture. All voices are heard regardless of tenure or job title. We are looking for creative problem solvers with a strong work ethic and ability to persevere. 

Role Description:

The People Operations/Payroll & Benefits Specialist will be responsible for overseeing all aspects of payroll, benefits and HRIS practices at ShipBob, Inc. They will develop, implement, and maintain policies, procedures, and forms; support department managers and employees regarding payroll , benefits and leave issues; and maintain personnel records in accordance with organizational/ regulatory requirements. The People Operations/Payroll & Benefits Specialist will report directly to the Director of People Operations in the interim and the People Operations Manager long term.



  • Process weekly and bi-monthly payroll for hourly, non-exempt and exempt team members in multi-state (Illinois, New York, California and Texas) using the ADP payroll system and Deputy time keeping system)
  • Review employees’ timecard for accuracy and for compliance with labor laws
  • Audit payroll entries for discrepancies and errors and job classifications
  • Review ADP (Payroll Service Company) reports, and prepare payroll reports for approval
  • Ensure all proper new hire paperwork is submitted relevant to payroll (offer letters, state and federal forms, I9’s & H1B documentation)
  • Assist employees with inquires and resolve issues related to payroll
  • Process and respond to garnishment notices
  • Manage the WOTC
  • Complete wage analysis reviews to ensure wages are competitive.
  • Develop, document, revise and train the payroll process for improved efficiency and accountability


  • Employee information maintenance in the ADP & Deputy systems.
  • Input and maintain employee records (new hire, transfer, personnel & payroll data updates, termination) both in computer system and in personnel files with accuracy and confidentiality
  • New hire orientation and onboarding management.
  • Prepare monthly and other HR related reports as assigned (turnover data, new hire & termination data, evaluation data).
  • Serve as liaison between ShipBob, Inc and ADP for unemployment data
  • Train managers on HRIS system uses and processes.


  • Review and maintain employee benefits (401K, health insurance, commuter benefits, COBRA)
  • Oversee and coordinate annual open enrollment period and new hire enrollment period
  • Coordinate with insurance providers to resolve any issues related 401K and insurance eligibility, COBRA, etc.
  • Coordinate with insurance provider for proper filing of Form 1095
  • Review year end compliance test results, form 5500 employee data and file Form 5500 for 401K plan
  • Prepare and distribute communication regarding benefits & wellness to employee
  • Review and reconcile monthly invoices and submit for payment
  • Research new ideas for benefit programs to take care of team members and keep company competitive.

Leave Management

  • Establish process and provide assistance to employees regarding leave (FMLA, CFRA, New York Paid Leave, California Paid Leave, Worker’s Compensation, etc.)
  • Prepare and provide the necessary forms to employees
  • Coordinate with W/C broker and carrier to manage W/C cases.
  • Other administrative duties
  • Coordinate with CPA to file annual tax returns of expatriate employees
  • Coordinate with immigration lawyer to prepare visa documents for expatriate employees.
  • Review and process HR related invoices (i.e. New York Paid Leave, etc…)

Qualifications Required:

  • Multi-state experience processing payroll and leave programs (specifically in California and New York).
  • 5-7 years experience processing payroll for company sizes above 300 employees.
  • 2-3 years of ADP HRIS & Payroll system experience

Additional Qualifications:

  • CPP certification a plus /SHRM-CP or PHR certification a plus.
  • Advanced computer skills to include data entry, Word, Excel and Adobe Acrobat.
  • Excellent/professional verbal and written communication skills.
  • Ability to interact and communicate with all levels within the organization.
  • Experience using Deputy time tracking system.
  • Strong initiative, ability to anticipate issues proactively.
  • Ability to succeed in a fast-paced environment.
  • Proven track record of reliability and responsibility.
  • Strong organizational and administrative skills. Detail oriented.
  • Discreet, able to handle confidential and proprietary information appropriately. High level of integrity.
  • Strong communication skills. Able to quickly respond to questions and make independent judgments about how to handle various administrative situations.
  • Meticulous attention to detail. Able to organize and categorize information to track, manage and follow through on necessary changes over time.
  • Problem solving skills.
  • Comfortable working independently or as part of a team with minimal supervision
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120 North Racine, Chicago, IL 60607

An Insider's view of ShipBob

What’s the vibe like in the office?

It's a very welcoming and collaborative work environment. Going to work isn't a chore, it's exciting!


Senior Business Development Representative

What projects are you most excited about?

I'm most excited about helping to create the road map for cool features that will help our customers drive more value for their business


Product Manager

How does the company support your career growth?

ShipBob supports my career growth by allowing me to focus on my preferred verticals while giving me all the resources needed to bring in new business. I am given complete responsibility to spearhead new projects that will continue to support other teammates and grow our company.


Senior Business Development Representative

How do your team's ideas influence the company's direction?

Our BDR team are the "Director's of First Impressions". We are the first point of contact with ShipBob. Being at the forefront of the customer experience, it is crucial that our vision shines through. The team is not only responsible for garnering interest, but shaping the relationship that will lead to a positive and fruitful partnership.


Business Development Manager

How has your career grown since starting at the company?

I’ve been given the opportunity to work on very interesting projects across different departments. I initially joined the Analytics team and just recently moved to Strategic Projects where I’m leading some of the initiatives we are working on. Shipbob is definitely a place where you can have an impact and be continually challenged!


Senior Manager, Strategic Projects

What are ShipBob Perks + Benefits

Volunteer in local community
Eat lunch together
Intracompany committees
Open door policy
Health Insurance & Wellness Benefits
Dental Benefits
Vision Benefits
Health Insurance Benefits
Retirement & Stock Options Benefits
Company Equity
Child Care & Parental Leave Benefits
Family Medical Leave
Vacation & Time Off Benefits
Unlimited Vacation Policy
Paid Holidays
Paid Sick Days
Perks & Discounts
Casual Dress
Commuter Benefits
Company Outings
Stocked Kitchen
Happy Hours
Recreational Clubs
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