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Payroll & Benefits Specialist

Boston, MA
  • Expired: over a month ago. Applications are no longer accepted.
Job Description

We'd love to hear from you if you like:

  • Making a big impact with a Forbes Top Startup Employer

  • Working at a startup that has traction (40X revenue growth in 4 years | #1 rated app in the insurance comparison category)

  • Working closely with serial entrepreneurs and seasoned leaders who have scaled companies like Robinhood, Amazon, LinkedIn, Wayfair, SoFi, Microsoft, etc.


About the opportunity:

We are looking for a Payroll and Benefits Specialist to join our team! You will be responsible for processing semi-monthly and weekly payrolls across multiple countries, ensuring that Jerry's payroll and benefits obligations are met in a timely manner in accordance with our internal policies, and that we are compliant with state, provincial, and federal government regulations. You will own the full scope of payroll and benefits administration for the entire lifecycle of all exempt and non-exempt employees, and contractors including tax rate changes, life events, leave administration, benefit enrolment, garnishments, deductions, and investigate and resolve pay issues and end user testing for payroll system changes to ensure a seamless payroll process with minimal gaps. 


  • Oversee our global payroll processing across the U.S., Canada, China, Ukraine, Poland, and the Philippines

  • Review and audit payroll for all exempt and nonexempt employees and contractors; work closely with managers of nonexempt employees to ensure time sheets are accurate and free from error

  • Administer benefit enrolments and terminations, leaves, and compensation adjustments 

  • Act as the main point of contact for our team members regarding benefits, leave and compensation including questions concerning employee leaves, 401(k), or other employee welfare programs and assist employees with electronic processes and comprehension of benefit plan design when needed

  • Ensure data integrity in all benefit vendor sites and HRIS regarding employee demographic and compensation information 


  • 3 years of experience managing global payroll including the U.S. across multiple states (preference for CA, WA, PA, and NY)

  • Prior experience setting up or updating internal controls to ensure payroll and benefits are accurately administered and compliant with state and federal regulations while ensuring optimal efficiency

  • Payroll certification. HR certificate is a plus!

Ideal Profile:

  • You have meticulous attention to detail

  • You are a creative problem solver

  • You are a strong communicator

Jerry is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.

Jerry is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at

About Jerry:

Jerry is building the first Super App to save car owners time and money on all their car expenses. Drivers deserve better. That’s why we’re committed to making shopping for insurance, financing, maintenance, repairs, parking and more just a few clicks, texts, or swipes away. 

Jerry is taking processes that haven’t substantively changed in decades and reimagining and redesigning them. Using artificial intelligence, machine learning and bots, Jerry eliminates the need for long forms and phone calls while providing personalized services for all car-owners’ needs. 

Today, Jerry is the #1 rated and most downloaded app in its category and the fastest way to compare and buy car insurance. We have more than 2M customers and we are just getting started. Join our team of curious and passionate people who love tackling real-world problems and be a part of building a revolutionary product that’s disrupting a massive market. 

Jerry was founded in 2017 by serial entrepreneurs and has raised more than $130 million in financing. 



Boston, MA



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