Benefits Specialist

At DraftKings, AI is becoming an integral part of both our present and future, powering how work gets done today, guiding smarter decisions, and sparking bold ideas. It's transforming how we enhance customer experiences, streamline operations, and unlock new possibilities. Our teams are energized by innovation and readily embrace emerging technology. We're not waiting for the future to arrive. We're shaping it, one bold step at a time. To those who see AI as a driver of progress, come build the future together.
The Crown Is Yours
As a Benefits Specialist, you'll be the go-to expert for supporting our people through life's moments. You'll play a key role in administering U.S. leave of absence (LOA) programs and health and welfare benefits, while championing wellbeing initiatives across the company. In this role, you'll guide our teams through navigating leave processes with empathy, enhancing benefit offerings with precision, and communicating programs clearly and effectively. You'll collaborate cross-functionally and with external vendors to deliver a seamless, supportive benefits experience.
What You'll Do as a Benefits Specialist

• Administer and manage U.S. leave of absence programs including FMLA, ADA, parental leave, and company-sponsored or state-mandated leaves.
• Serve as the primary contact for employees and managers throughout the leave lifecycle, including eligibility, documentation, tracking, and return-to-work coordination.
• Partner with third-party administrators to ensure timely, accurate leave processing and service delivery.
• Support day-to-day administration of health and welfare benefit plans, including medical, dental, vision, life, disability, and supplemental benefits.
• Coordinate logistics for open enrollment, benefit renewals, plan audits, and vendor relationships.
• Lead communications related to benefits, leaves, and wellbeing in clear, accessible formats for all employees.
• Plan, implement, and evaluate wellbeing programs that promote mental, physical, emotional, and financial health.
• Organize wellness events and manage vendor partnerships for initiatives such as EAP, fitness programs, and financial planning sessions.

What You'll Bring

• Bachelor's degree in Human Resources, Business Administration, or a related field or equivalent experience.
• At least 3 years of experience administering employee benefits, with a focus on LOA and health and welfare plans.
• Strong understanding of federal and state leave laws (e.g., FMLA, ADA, CFRA) and benefits compliance (ERISA, ACA, HIPAA).
• Experience working with third-party vendors and benefits brokers.
• Proficiency in HRIS systems such as Workday, ADP, or SAP, along with Microsoft Office Suite.
• Excellent written and verbal communication skills with the ability to clearly explain complex policies.
• Strong organizational skills with the ability to manage multiple programs and priorities simultaneously.
• A passion for improving the employee experience through empathetic service and thoughtful benefit offerings.

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Join Our Team
We're a publicly traded (NASDAQ: DKNG) technology company headquartered in Boston. As a regulated gaming company, you may be required to obtain a gaming license issued by the appropriate state agency as a condition of employment. Don't worry, we'll guide you through the process if this is relevant to your role.
The US base salary range for this full-time position is 88,000.00 USD - 110,000.00 USD, plus bonus, equity, and benefits as applicable. Our ranges are determined by role, level, and location. The compensation information displayed on each job posting reflects the range for new hire pay rates for the position across all US locations. Within the range, individual pay is determined by work location and additional factors, including job-related skills, experience, and relevant education or training. Your recruiter can share more about the specific pay range and how that was determined during the hiring process. It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.