We power successful restaurants.
Boston, MA

Leave Administrator (LOA) at Toast

| Greater Boston Area | Remote
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Now, more than ever, the Toast team is committed to our customers. We’re taking steps to help restaurants navigate these unprecedented times with technology, resources, and community. Our focus is on building the restaurant platform that helps restaurants adapt, take control, and get back to what they do best: building the businesses they love. And because our technology is purpose-built for restaurants, by restaurant people, restaurants can trust that we’ll deliver on their needs for today while investing in experiences that will power their restaurant of the future.

Bready* to make a change?

Our People Operations team supports and enhances the employee journey by evolving our processes and systems as we scale.  We meet Toasters in moments that matter. By enabling the business with tools and efficient processes, we support all Toasters to thrive through providing a reliable and positive employee experience.

This roll* is responsible for the day-to-day administration of all employee leaves of absence, including leaves qualifying under Toast’s leave and time-off policies, state and local leave laws and workers’ compensation. This is a great opportunity to be a subject matter expert on a growing team where you can use your process improvement skills to create efficiencies.  The ideal candidate will have fierce organization skills and a commitment to ensuring great experiences for Toast employees and managers.  

Job Overview:

The People Operations Leave Administrator is responsible for administering and managing Toast’s leave programs, supporting employees, collaborating with our leave administration vendor, partnering with the People Success Team and communicating with managers regarding leave statuses to help them plan their the day-to-day business operations while employees are out on leave.

What you will do:

  • Communicate with employees regarding their needs for leave and/or modified work schedules, the benefits available to them, and ensure they have the information needed to file a claim with our third party vendor. 
  • Maintain communication with our third party vendor, as well as with employees on leave and their managers to facilitate a smooth and timely return to work.
  • Advise employees and managers on the interaction of leave laws with paid time off, workers’ compensation, and short-term and long-term disability benefits.  Handle inbound inquiries and escalate complex issues as needed.
  • Ensure accurate employee information is processed in Workday and processed to Payroll on a timely basis.
  • Recommend revisions to company leave policies to ensure compliance with federal, state, and local laws and regulations.
  • Maintain complete and accurate records of leave and accommodation requests in accordance with specified legal requirements and documentation of best practices.
  • Preserve confidentiality of employee medical documentation and files.
  • Maintain knowledge of all applicable leave and accommodation laws including the FMLA, ADA, and state and local laws.
  • Proactively identify process improvements and collaborate towards a more productive process that improves the employee and manager experience.
  • Perform other related duties or special projects as necessary.

Do you have the right ingredients?

The ideal candidate in this role will be customer-oriented, will genuinely enjoy working with people, and will have the ability to successfully manage multiple high priority tasks.  Additional required qualifications include:

  • Extensive knowledge of the leave requirements and other legal protections afforded by the FMLA, ADA, and other applicable laws.  
  • Experience working in a HR department preferred, with a minimum of 3 years of experience; Co-op and internship experience will be considered.
  • Prior experience working with outsourced leave of absence service providers or insurance companies is a plus.
  • Demonstrated customer service skills and the ability to work well with people.
  • Excellent organizational and problem-solving skills and an unwavering commitment to accuracy.
  • Experience with Workday, ServiceNow, or other HRIS systems is a plus.
  • Excellent written and oral communication skills.
  • Ability to work with confidential information and maintain discretion.
  • Bachelor’s Degree in a Human Resources related field preferred.
  • Completion of specialized certification or training on FMLA/leave administration is a plus.


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!

For roles based in the United States:  As part of our commitment to the health and safety of our employees and their families, all individuals entering our US workspaces are required to provide proof of full vaccination against COVID-19 unless they have an approved medical or religious accommodation.

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Where we are

Toast is headquartered in the heart of Fenway. Catch a Sox game, grab a bite, and stroll through one of the trendiest neighborhoods in Boston.

Technology we use

  • Engineering
    • JavaLanguages
    • JavascriptLanguages
    • KotlinLanguages
    • jQueryLibraries
    • ReactLibraries
    • AngularjsLibraries
    • ES6Libraries

What are Toast Perks + Benefits

Toast Benefits Overview

Toast strives to provide competitive compensation and benefits programs that help to attract, retain, and motivate the best and brightest people in our industry. Our total reward package goes beyond great earnings potential and provides the means to a healthy lifestyle with the flexibility to meet our employees’ changing needs.

Volunteer in local community
Partners with Nonprofits
Friends outside of work
Eat lunch together
Intracompany committees
Daily sync
Open door policy
Team owned deliverables
Team based strategic planning
Group brainstorming sessions
Open office floor plan
Dedicated Diversity/Inclusion Staff
Unconscious bias training
Diversity Employee Resource Groups
We have 14 employee resource groups, known as Toast Communities, dedicated to empowering employees.
Hiring Practices that Promote Diversity
Health Insurance & Wellness Benefits
Flexible Spending Account (FSA)
Disability Insurance
Dental Benefits
Vision Benefits
Health Insurance Benefits
Life Insurance
Pet Insurance
Wellness Programs
Team workouts
Mental Health Benefits
Retirement & Stock Options Benefits
401(K) Matching
Company Equity
Performance Bonus
Child Care & Parental Leave Benefits
Child Care Benefits
Generous Parental Leave
Flexible Work Schedule
Remote Work Program
Family Medical Leave
Company sponsored family events
Vacation & Time Off Benefits
Unlimited Vacation Policy
Paid Volunteer Time
Paid Holidays
Paid Sick Days
Perks & Discounts
Beer on Tap
Casual Dress
Commuter Benefits
Company Outings
Game Room
Stocked Kitchen
Happy Hours
Recreational Clubs
Fitness Subsidies
Home Office Stipend for Remote Employees
Professional Development Benefits
Job Training & Conferences
Diversity Program
Lunch and learns
Cross functional training encouraged
Promote from within
Mentorship program
Time allotted for learning
Online course subscriptions available
Customized development tracks

An Insider's view of Toast

How would you describe the company’s work-life balance?

Toast is a pretty special place to work. I really enjoy the collaborative and supportive work culture. Toast goes out of its way to take care of employees through additional days off to flexible hours to peer groups and training.


Senior Engineering Manager

How do you collaborate with other teams in the company?

Being a part of the R&D team, I collaborate closely with cross-functional partners like Product, Design, Quality and Documentation to ensure alignment across the team and ultimately execution. Since joining Toast, I have been stretched both technically and non-technically, grown my career and become a stronger engineer and a more effective leader.


Manager, Software Engineering

How has your career grown since starting at the company?

I began as an Implementation Engineer, moved into instructional design, and now I am in my dream role as a Product Manager. This is afforded because Toast fosters a culture where experts in their domains are eager to give you a masterclass in what they do – you only need to ask and be willing to learn. This is the best perk when working at Toast.

Sean Park

Product Manager

What unique initiatives do you have that encourage innovation?

I love our bi-annual company-wide Hackathons! The mission is to provide all Toasters with the opportunity to innovate on Toast’s products, processes, & culture while fostering new connections between teams and people. I absolutely love seeing Toasters come together; the energy, enthusiasm, & passion for making Toast better is incredibly inspiring!


Senior Director of Product Management

How does the company support your career growth?

When Toast hires you, they immediately invest in you and give you every bit of support to ensure you are not only successful but in the best position for growth. Aside from the great support resources, Toast has a team of some of the smartest people in tech that I've been able to learn from.


Senior District Sales Manager

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