Senior US Benefits Specialist

Posted 13 Days Ago
Be an Early Applicant
Boston, MA
88K-141K Annually
Senior level
Cloud • Fintech • Food • Information Technology • Software
We power successful restaurants.
The Role
The Senior Benefits Specialist at Toast is responsible for overseeing employee benefits programs, ensuring compliance with regulations, analyzing benefit plan costs and trends, managing vendor relationships, and leading open enrollment activities. The role requires strong analytical skills and collaboration with HR teams to enhance benefits offerings for employees.
Summary Generated by Built In

Toast is driven by building the all-in-one restaurant platform that helps restaurants operate their business, increase sales, engage guests, and keep employees happy. The Senior Benefits Specialist is responsible for the design, administration and communications of Toast employee benefits programs in the U.S. This role requires a strong understanding of benefits administration, applicable regulations, excellent analytical skills, and a passion for designing programs that support Toast employees in the moments that matter. 


About this roll* (Responsibilities) 

Benefits Administration:

    • Partner with Toast’s HRIS and vendor partners to successfully administer US employee benefit programs, including health, dental, vision, life insurance, disability, 401(k), flexible spending accounts, and wellbeing programs/stipends. 
    • Partner with Toast’s HRIS systems team to improve Workday’s capabilities to automate benefits administration processes. Manage operational aspects of vendor management, including, but not limited to HRIS integrations, development of required Workday reporting, and troubleshooting enrollment issues 
    • Ensure compliance with all applicable federal, state, and local regulations (e.g., ACA, COBRA, HIPAA, ERISA, State Leave Compliance), such as completion of non-discrimination testing and audit on the Toast 401(k) plan.
    • Manage relationships with Toast’s benefits broker and Toast’s vendor partners; hold external consultants accountable to identified timelines and deliverables
    • Within Toast’s procurement program, set up purchase orders, reconcile benefit invoices and resolve discrepancies.

Benefits Program Analysis and Implementation:

    • In partnership with the benefits team and Toast’s external brokers, select new vendors and complete implementation with internal partners, including procurement, finance, and HR. 
    • In partnership with Toast’s brokers and vendors, review benchmarking studies to evaluate the competitiveness of benefit offerings.
    • Analyze benefit plan costs, utilization, and trends.
    • Develop and present recommendations for benefit plan design changes.

Employee Support:

    • Partner with Toast’s talent operations team to support employee inquiries on the programs, including questions, qualifying life event changes in coverage, and coordination of exit packages.
    • Execute on Toast benefits communications strategy, inclusive of employee facing communications, and maintain accurate and supportive information on The Pantry, Toast’s intranet. 
    • Respond to escalated issues to support Toasters in advocating on behalf of Toaster with vendor partner and Toast’s benefits broker. 

Open Enrollment

    • Lead annual US open enrollment activities
    • Collaborate with the HR Systems and Payroll teams on benefit plan changes that require changes to Toast Workday benefits application and payroll deductions
    • Develop a communication approach to share annual open enrollment updates and execute on approach with Toast vendors.

Process Improvement & Project Management

    • In alignment with Toast’s evolving operating model, improve processes by transitioning certain workstreams to Toast’s Talent Operations team. 
    • Provide subject matter expertise in supporting internal improvement projects
    • Project manage the benefits team, identifying key milestones, documenting progress in Asana in support of keeping deliverables on track year over year. 



Do you have the right ingredients*? (Requirements)

  • Bachelor's degree in Human Resources, Business Administration, or a related field.
  • 5+ years of experience administering employee benefits programs in a corporate or consulting environment.
  • Strong knowledge of benefits laws and regulations, including federal, state, and local regulations (e.g., ACA, COBRA, HIPAA, ERISA).
  • Excellent analytical, problem-solving, and project management skills.
  • Proficiency in Google Suite, Microsoft Excel, and Workday HRIS systems.
  • Strong communication and interpersonal skills.
  • Ability to work independently and as part of a team.



Special Sauce* (Nice to Haves)

  • Experience with benefits administration in a high-tech environment is a plus.



Our Spread* of Total Rewards
We strive to provide competitive compensation and benefits programs that help to attract, retain, and motivate the best and brightest people in our industry. Our total rewards package goes beyond great earnings potential and provides the means to a healthy lifestyle with the flexibility to meet Toasters’ changing needs. Learn more about our benefits at https://careers.toasttab.com/toast-benefits.


The base salary range for this role is listed below. The starting salary will be determined based on skills and experience. In addition to base salary, our total rewards components include cash compensation (overtime, bonus/commissions if eligible), equity, and benefits.

Pay Range

$88,000$141,000 USD


We are Toasters

Diversity, Equity, and Inclusion is Baked into our Recipe for Success.

At Toast our employees are our secret ingredient. When they are powered to succeed, Toast succeeds.

The restaurant industry is one of the most diverse industries. We embrace and are excited by this diversity, believing that only through authenticity, inclusivity, high standards of respect and trust, and leading with humility will we be able to achieve our goals.

Baking inclusive principles into our company and diversity into our design provides equitable opportunities for all and enhances our ability to be first in class in all aspects of our industry.

Bready* to make a change? Apply today!

Toast is committed to creating an accessible and inclusive hiring process. As part of this commitment, we strive to provide reasonable accommodations for persons with disabilities to enable them to access the hiring process. If you need an accommodation to access the job application or interview process, please contact [email protected].

Top Skills

Compliance Regulations
Employee Benefits Administration
Google Suite
Hris Systems
Excel
Workday

What the Team is Saying

Colleen Miller
Kyle Armillotti
Emmy Wright
Brad
Sean Park
Eden
Jane
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The Company
Boston, MA
4,500 Employees
Hybrid Workplace
Year Founded: 2011

What We Do

We're not your traditional tech company, and we don't aim to be. At Toast, people can truly bring their full selves to work. Together, we empower restaurants of all sizes to build great teams, increase revenue, improve operations, and delight their guests through an intuitive all-in-one platform.

Why Work With Us

Our recipe for an awesome workplace:

One splash of friendship
A dollop of impact
A sprinkle of no hierarchy &
A heavy spoonful of individuality

Mix these ingredients in a fast-paced and hardworking environment. Best paired with a side of interesting people who always bring their whole selves to work.

*100% Sunday scary free

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Toast Offices

Hybrid Workspace

Employees engage in a combination of remote and on-site work.

Typical time on-site: Flexible
Boston, MA

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