Senior Benefits Associate

Boston, MA

DraftKings Inc. (Nasdaq: DKNG) is a digital sports entertainment and gaming company. It’s simple, at DraftKings, we believe life’s more fun with skin in the game. For that reason, we’re committed to responsibly creating the world’s favorite games and betting experiences. Headquartered in Boston, MA, with offices around the globe, we believe we can continue to define what it means to be a technology company in sports entertainment. We love what we do, and think you will too.

Join a groundbreaking team.
We’re growing rapidly and are searching for a Senior Benefits Associate to join our Total Rewards organization. When you join us, you will support the administration of retirement, health, and welfare employee benefit programs. This can include assisting in the business development and planning processes with service providers, compiling and analyzing reports and data, and planning financials for strategic benefits evaluation. Sound good to you? Join us.

What you’ll do as a Senior Benefits Associate:

  • Monitor eligibility, limitations, and restrictions of plan participations and ensure compliance with both plan provisions and government requirements.
  • Provide guidance and counsel to employees, HRIS representatives, and managers on the requirements and provisions of benefit programs and assist with the resolution of potential problems.
  • Coordinate the communication of annual benefit enrollment materials and Total Reward Statements.  
  • Draft legal compliance documentation (SPDs, SARs).
  • Develop, conduct and participate in a variety of presentations to inform and educate all of our team members about changes to benefit plans, administrative practices and legislated requirements.
  • Prepare bid specifications analyze proposals and renewal information and interpret insurance carrier contracts.
  • You will also be responsible for the data necessary to complete government compliance activities (5500s, audits, etc.), employee mailings, vendor billings, coordinating data collection, and updating numerous reports for management.
  • Oversee/direct the administration of COBRA compliance.
  • Research current benefit trends and regulatory/legislated requirements and recommend changes to the Director of Employee Benefits.
  • Compile, analyze and report benefit data including employee, benefit plan and financial for Benefit's strategic planning and evaluation, best practices and benchmark surveys.

What skills you will use:

  • Ideally, you have at least 1-3 years of related experience.
  • Demonstrated basic knowledge of ERISA, employee benefit programs, including self-funded and flexible benefit programs, financial analysis, and budgeting.
  • You have a strong customer service and analytical mindset.
  • Ability to perform mathematical calculations in computing rates, premiums, and adjustments.
  • You’re proficient with Microsoft Office products.
  • You are able to develop and maintain reporting standards where applicable.
  • You also have project management experience overseeing simultaneous projects.
  • Comfortable working independently and making proactive decisions.
  • You are open to change and new ideas. You love collaboration and teamwork.
  • You have a bachelor's degree in Human Resources or a related field with an emphasis in business or finance, or you have the equivalent professional experience related to the position.
Who are we a good fit for?
We love working with talented people but more than that, we seek out compassionate co-workers with a collaborative spirit. Our work moves quickly and we’re great at coming together to find creative solutions to some of tech’s most interesting problems. If that sounds good to you, join us.

Apply now
As a technology company at our core, DraftKings believes that the best innovation comes from diverse perspectives, thoughts, beliefs, ideas, and experiences. We consistently push boundaries and challenge the conventional to ensure our culture and products reflect the expectations of our employees, and the customers we serve.

We’re proud to believe that your gender, race, nationality, religion, sexual orientation, status as a protected veteran, or status as an individual with a disability should have nothing to do with our hiring practices. We’ll never discriminate against anyone’s background or creed. If you’re good at what you do, we want you to do it at DraftKings.


You may be required to become licensed through applicable regulatory agencies.

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