Benefits Analyst – Leaves & Accommodations


  • Full Time

See yourself at Twilio.

Join the team as our next Benefits Analyst – Leaves & Accommodations.

Who we are & why we’re hiring

Twilio powers real-time business communications and data solutions that help companies and developers worldwide build better applications and customer experiences.

Although we're headquartered in San Francisco, we're a remote first company and on a journey to becoming a globally antiracist company that supports diversity, equity & inclusion wherever we do business. We employ thousands of Twilions worldwide, and we're looking for more builders, creators, and visionaries to help fuel our growth momentum.

About the job

This position reports to the Manager, Global Leaves & Accommodations and is a strategic partner on the Twilio Global Leaves team (within the Global Benefits group in the People Team). This person will support the leave of absence, time-off and accommodation programs for over 5,000 employees in the US & Canada. The role will serve as a leave & time-off expert and point person in a fast paced and dynamic environment. The Global Leaves team partners closely with the N. America Benefits team (within Global Benefits) who are responsible for all health, risk, retirement and well-being programs. 

This team (Global Benefits) ensures our benefit offerings provide support and meets the current and future needs of all Twilions. We are focused on scaling our capabilities to align with Twilio’s growth by ensuring we are operating efficiently and effectively. We prioritize delivering excellent customer service when employees interact with internal and external benefit team partners.


In this role, you will:

  • Serve as a day-to-day program owner and an expert on Twilio leave of absence, time-off and accomodations for the North America region (US & Canada):
    • Be the primary contact for employee inquiries regarding our leave and time away programs, responding to inquiries in a timely manner
    • Work collaboratively with employees and our leave vendor (Prudential), responding to questions and resolving issues, following processes and complying with federal and state regulations
    • Collaborate with Payroll team to ensure accurate leave of absence details are gathered and shared timely to meet US/Canada payroll deadlines
    • Utilize HR information system (Workday) and Prudential system as needed to input and update leave data and generate reports
    • Ensures that employees are aware of their responsibilities and of any documentation and notice required to qualify for and to take leave
    • Partner with leaves vendor (Prudential) on the day-to-day leave process by managing workflow, including tracking all leave of absences, identifying discrepancies, obtaining necessary approvals and/or following-up on outstanding issues
    • Ensure a smooth return to work transition for the employee; coordinate return with the manager considering any restrictions that may need to be accommodated
    • Gather critical data as requested (case notes, LOA dates, etc.)
    • Successfully manage employee escalations, invoicing, pay & disability payment coordination with payroll and external vendor
  • Support program and vendor management 
    • Understand program design, requirements and vendor capabilities
    • Continuously create process and program efficiencies – example, ensure process are being automate whenever possible and the Twilio Leaves team isn't managing things that should belong with the vendor or another Twilio team
    • Vendor management – ensure vendor is performing at the levels we want, is delivering on the employee experience we want and helping us track & manage priorities relating to the program
    • Data & Analytics – receive Twilio program reporting from vendor or internal systems that can be leveraged as needed (example, help identify employee engagement opportunities, effectiveness of the programs etc.)
    • Communications to employees – have visibility to all communications being sent to employees by vendors or other teams
  • Work collaboratively with teams across Twilio (e.g., HRBP’s, Payroll, Legal, Communications, People Technology, Facilities, Finance, Procurement etc.)


Not all applicants will have skills that match a job description exactly. Twilio values diverse experiences in other industries, and we encourage everyone who meets the required qualifications to apply. While having “desired” qualifications make for a strong candidate, we encourage applicants with alternative experiences to also apply. If your career is just starting or hasn't followed a traditional path, don't let that stop you from considering Twilio. We are always looking for people who will bring something new to the table!


  • 3+ years experience managing US leaves and time-off programs or a similar role on the consulting/TPA side. 
  • Ability to effectively interpret Family & Medical Leave Act (FMLA), Americans with Disabilities Act (ADA) and other applicable federal and state laws, as they relate to leaves of absences/disabilities
  • Experience with leaves/benefits program management including administration, compliance, employee education/engagement, data analytics & financials.
  • Excellent oral and written communication skills.
  • Strong interpersonal skills and ability to maintain effective working relationships with internal & external partners.
  • Ability to interface with all levels of employees.
  • Ability to prioritize and maintain flexibility in a fast-paced, changing environment.
  • Attention to detail, organizational, and project management skills. 
  • Must be comfortable using Excel or other applications to analyze data. Ability to gather, check and analyze complex information and data and effectively communicate findings.
  • Continuous focus to monitor and improve operations, decrease turnaround times, streamline work processes, and work collaboratively across internal teams to provide effective customer service to employees.
  • Results driven & problem-solver.
  • Strong business acumen with ability to engage and inform key stakeholders as needed.
  • Will take the initiative to drive projects forward even under ambiguous circumstances.


  • Bachelor’s Degree in a related field (Business, Finance, HR) or high school diploma plus hands-on relevant experience in lieu of degree
  • Managed leave & time-off programs at mid to large organization(s) (at least 5k+ ee’s)
  • Experience working as part of a remote team 
  • Worked for a multinational company


This role can be remote or located at one of Twilio’s US locations. Approximately 5% travel is anticipated.

What we offer

There are many benefits to working at Twilio, including things like competitive pay, generous time-off, ample parental and wellness leave, healthcare, a retirement savings program, and much more. Offerings vary by location.

Twilio thinks big. Do you?

We like to solve problems, take initiative, pitch in when needed, and are always up for trying new things. That's why we seek out colleagues who embody our values — something we call Twilio Magic. Additionally, we empower employees to build positive change in their communities by supporting their volunteering and donation efforts.

So, if you're ready to unleash your full potential, do your best work, and be the best version of yourself, apply now!

If this role isn't what you're looking for, please consider 

*Please note this role is open to candidates outside of Colorado as well. The information below is provided for those hired in Colorado only.

*If you are a Colorado applicant:

  • The estimated pay range for this role, based in Colorado, is $67,760 – $93,170.
  • Sales Commission: Additionally, this role is eligible to earn commissions and eligible to participate in Twilio's equity plan.
  • Non-Sales: Additionally, this role is eligible to participate in Twilio's equity plan.

The successful candidate’s starting salary will be determined based on permissible, non-discriminatory factors such as skills, experience, and geographic location within the state. This role is also eligible to participate in Twilio’s equity plan and for the following benefits: health care insurance, 401(k) retirement account, paid sick time, paid personal time off, paid parental leave.

Twilio is proud to be an equal opportunity employer. Twilio is proud to be an Equal Employment Opportunity and Affirmative Action employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics. We also consider qualified applicants with criminal histories, consistent with applicable federal, state and local law. Additionally, Twilio participates in the E-Verify program in certain locations, as required by law.

Twilio is committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. If you need assistance or an accommodation due to a disability, please contact us at