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US Payroll & Benefits Manager



Accounting & Finance
Cambridge, MA, USA
Posted on Tuesday, March 5, 2024

Why us?

Insurify is one of the America’s fastest-growing MIT FinTech startups and has been recognized as one of Inc. 5,000’s fastest-growing private companies in America of 2023, 2022 and 2021, Forbes Fintech 50 List for 2023, 22, 21, Forbes Next Billion Dollar Startups of 2022 global and Top 100 InsurTech company. We’re changing the way millions of people compare, buy and manage insurance with artificial intelligence, technology, and superior product design. Our company vision is to be recognized as the preeminent and most trusted digital agent for insurance comparison, purchase, and management. Our team is critical to achieving our vision and fostering the right culture is essential to our team’s success.

Join us if you like

  • $1.3 Trillion market opportunity
  • MIT alumni founders
  • Female-led startup
  • $130M total funding
  • Strong leadership team with experience from many successful start-up’s around the world

How you will make an impact

Calling all Payroll & Benefit geeks! Insurify is seeking a seasoned and exceptional candidate to build and lead the payroll and benefits administration for our 100+ US employees..

This is truly an exciting time to join! Historically, these functions have been shared among several areas of the company. We’ve recently made the decision to bring them under the People & Culture team into this newly created role. We believe that focused attention and investment in these areas will allow us to more effectively and efficiently serve our employees.

This role will report directly to the Global Head of People & Culture and will be responsible for evaluating current tools and processes and researching and recommending new projects, initiatives and approaches. Among other things, the ideal candidate will bring a positive can-do attitude and a passion for HR.

Primary Areas of Focus:

  • Payroll - Ownership of the end-to-end payroll process for 100 US employees . Ensuring all aspects of payroll are completed timely, accurately, and in compliance with all state and federal laws.
  • Benefit Management & Strategy - Ownership of the health, wellness, and financial benefit areas including plan assessment/design, administration, and implementation of benefit programs to ensure competitiveness, cost effectiveness and compliance with all state and federal laws. Maintain strong relationships with vendors and external brokers to ensure the most optimal pricing is negotiated on existing and new benefit programs.
  • Leave of Absences - Manage LOAs to ensure proper administration and compliance with the FMLA, ADA, and Workers Compensation. Assure compliance of all government regulations affecting employee benefit programs; keep abreast of pending legislation and its potential impact upon the company. Advise department managers and employees on interpretations of benefit policies and practices.
  • Continuous Improvement - Responsible for ongoing review and improvement of internal processes and tools. Partner with the People & Culture team on policy implementation and amendments. Design and maintain effective internal controls for the function.
  • Communication - Ownership of overall communication strategy to ensure current and new employees understand their pay and benefits package, including any changes or updates. Act as point of contact for all employee inquiries related to benefits, pay, LOAs.
  • Reporting & Data Management - Responsible for ensuring people data is accurate in our systems and partnering with key stakeholders (ex finance, leadership) to assist with reporting needs.

The position responsibilities outlined above are in no way to be construed as all encompassing. Other duties, responsibilities, and qualifications may be required and/or assigned as necessary.

Who you are


  • Bachelor’s degree in Human Resources, Business Administration, Finance or related field
  • Proven experience in a payroll/benefits role with 4+ years of payroll management experience and 2+ years of benefits management experience
  • Fluent in English (knowledge of Bulgarian a plus)

Additional Skills/Experience:

  • Ability to work from our Cambridge, MA office 3 days per week (Tue, Wed, Thur)
  • Proven ability to implement new tools and processes resulting in measurable results
  • Experience working at a start-up or company with 50-200 people
  • Significant experience in the knowledge, design and implementation of HRIS and benefits programs
  • Knowledge of ERISA, HIPAA, COBRA and emerging regulatory issues preferred
  • Knowledge of state payroll tax issues
  • Exceptional communication skills and attention to detail
  • Demonstrated proficiency with Excel and Google Workspace (Sheets, Docs, etc.)
  • Ability to demonstrate sound judgment in working through complex transactions, with the ability to analyze, problem solve and communicate observations and recommendations
  • A proactive, thoughtful and timely approach to communication, analysis and problem solving.


  • Competitive compensation
  • Generous stock options
  • Health, Dental Coverages
  • 401K plan with match
  • Unlimited PTO
  • Generous company holiday calendar
  • Learning & Development Stipends
  • Paid Family Leave
  • Social impact volunteer time and donation matches
  • Catered lunches in the office
  • Commuter Benefits
We are proud to be an Equal Employment Opportunity and Affirmative Action employer.