Toast: Senior Benefits Analyst
401 Park Drive
Boston, MA 02215

Employee Testimonials

Maura Grimes Toast
Edmund Korley Toast
Kendal Austin Toast

Office Tour Photos


We are looking for an enthusiastic, organized, and detail-oriented Senior Benefits Analyst to join our People and Culture Team. Reporting to the Director, People and Culture, the Benefits Specialist will be responsible for the administration, compliance, and management of all benefit programs for our employees throughout the US and Dublin.

The Senior Benefits Analyst will be friendly and helpful, comfortable with handling highly confidential information and will know how to prioritize work and understand the balancing act of managing multiple projects simultaneously. The ideal candidate thrives in a fast-paced environment, and has excellent analytical and communication skills.

What you will do:

  • Primarily responsible for all aspects of the development, administration, and compliance of benefit programs including health and welfare benefits, retirement benefits, and wellness initiatives.
  • Develop, recommend and implement new/modified benefit plans, policies, and process improvements.
  • Respond to and ensure resolution of employee inquiries regarding benefit plans.
  • Develop and deliver benefit communications including employee onboarding, open enrollment, and other initiatives.
  • Ensure compliance with all federal and state legal requirements for qualified plans including plan documents, summary plan descriptions, vendor contracts, policy manuals, compliance testing, audits, and government filings.
  • Serve as the primary liaison with all vendors and auditors for benefit plan administration, funding, account reconciliation, premium payments, employee changes, cost analysis tracking, annual open enrollment, and compliance activities.
  • Perform quality checks of benefits-related data to ensure accuracy.
  • Work with management and employees to process and support all leaves of absence including FMLA, ADA, medical, parental, etc.
  • Handle Affordable Care Act (ACA) compliance reporting.
  • Keep our internal and external website up to date with current benefit information.
  • Perform other benefit projects as necessary.

Do you have the right ingredients?

The ideal candidate in this role will be customer oriented with strong organization skills, the ability to manage multiple high priority tasks with tight deadlines, while maintaining an impeccable attention to detail and accuracy. Additional qualifications are:

  • 5+ years experience working in a HR department focused on benefits administration required
  • International benefits experience a plus
  • Experience with Workday preferred, other HRIS systems will be considered
  • Excellent analytical skills; ability to research, collect, compile and analyze data
  • Knowledge of pertinent benefits-related federal and state regulations, filing and compliance requirements
  • Ability to work with confidential information and maintain discretion

Employee Testimonials

Maura Grimes Toast
Maura Grimes
Field Service Coordinator

"Ahh toast is awesome! The people, the culture, the bouncy balls, the crazy customers, the killer POS system, and the incredible talent floating through the air. "

Edmund Korley Toast
Edmund Korley
Software Engineer

"I've been participating in the Toast2Toast mentoring project. As a relatively new engineer at Toast, getting the opportunity to discuss technical (and other) topics with a mentor has been really valuable."

Kendal Austin Toast
Kendal Austin
Sr. Marketing Manager

"I have a degree in Marketing Communications and have worked in B2B technology my entire career. My background ranges from social media to paid programs to product marketing. I heard about Toast from a mentor and was connected with the co-founder on LinkedIn. As the second Marketing hire at Toast, I've had the opportunity to be a generalist as well as a specialist, moving where I was needed as the team grew."

Archie Grace Toast
Archie Grace
Engineering Manager

"I looked at a lot of start-ups during my last job search and Toast was by far the most exciting. It was instantly obvious to me how the product is useful to people and why someone might want to buy it. The proof of that has been in the way we have grown and the excitement we have already generated. However, what really excites me about the company is that I feel like we are just scratching the surface in terms of what we can accomplish. There are SO many untapped opportunities around our product and as we continue to grow, I am excited about being able to explore them more.​"