<< Back to Careers

Benefits Specialist

ZwillGen is a boutique law firm that represents some of the biggest names in technology on a range of Internet-related legal issues including cybersecurity, privacy, government surveillance, alternative data, and fantasy sports. We offer a hard-working, joyful, and casual work environment. We value a strong knowledge of pop culture and a good sense of humor!

ZwillGen PLLC is looking for a Benefits Specialist who is ready to hit the ground running, and hungry for a challenge! This position will be responsible for the administration of all benefits and retirement programs, including medical, dental, vision, life insurance, short- and long-term disability, and 401(k) plan. The Benefits Specialist will report to the Director of Human Resources. In addition to the traditional responsibilities below, we strongly encourage our staff to improve on established methods, seek out inefficiencies, and help build an infrastructure that can support a growing firm.


  • Ensure timely employee enrollments and terminations from all insurance/benefit plans.
  • Conduct regular audits to ensure proper deductions from payroll.
  • Ensure that all appropriate notices to employees following Federal and State Laws governing the continuation of benefits and coverage certification are communicated promptly and accurately.
  • Audit and monitor employees’ enrollment with carriers and process life status changes.
  • Process and administer all leave-of-absence requests and disability paperwork: medical, personal, disability, and FMLA.
  • Respond to 401(k) inquiries from managers and employees relating to enrollments and 401k match contribution amounts.
  • Assist with auditing the 401k plan periodically to include the company match and assist with the annual 5500 compliance requirements.
  • Assist with the open enrollment process and activities including presentations, preparing open enrollment materials, communications, and other related activities.
  • Ensures the timely and accurate processing of all monthly billings and invoices related to benefits administration.
  • Work closely with the IT and benefits team and lead benefit/HRIS system configurations and testing and development of any new automations.
  • Assist with the processing of 5500s and non-discrimination testing with third-party providers.
  • Manage ACA compliance-related projects including Form 1095c, Federal and State mandated filings, etc.
  • Responds to benefits inquiries from managers and employees on plan provisions, benefits enrollments, status changes, and other general inquiries.
  • Directs the effective administration of leave policies, compliance and regulatory reporting, and HR documentation management. 
  • Assist with the administration of the workers’ compensation program, including claims monitoring and administration, report generation, and communication with employees, managers, and insurance carriers when needed.
  • Provides counsel to Executives and employees regarding benefit policies and practices. 
  • Develop, automate, and analyze ongoing and ad-hoc special reports pertaining to duties and responsibilities as assigned.
  • Streamline and automate processes and other projects as assigned.


  • Bachelor’s degree in Human Resources or related field of study.
  • At least 5 years of experience in the administration and management of benefit plans.
  • Must be technically competent and remain up to date with legal requirements affecting benefit programs, including, but not limited to, SCA, ERISA, COBRA, HIPAA, FMLA, and Section 125, with an ability to apply that knowledge to the administration and formation of benefit plus
  • SHRM-CP and/or PHR certification is a plus.

This position is available on a hybrid or fully in-office basis in our Washington D.C. office.

Bonus Points

Good sense of humor.


  • $70,000 – $85,000 depending on experience, plus benefits.

If you are qualified and interested in this position, please email your resume to recruiting@zwillgen.com.

Our Culture

ZwillGen is not your typical law firm. We take our work seriously, but we don’t take ourselves too seriously.