Employee Support Specialist

DraftKings Inc.; Boston (MA); On-site; CAD 60,000 - 90,000; Full time

Job summary

DraftKings Inc. is seeking an Employee Support Specialist to manage Global Mobility, immigration, and leave cases from intake to resolution. You will guide employees through processes, explain eligibility and timelines, and maintain accurate records in Workday and JustAsk.

You will handle sensitive, compliance-driven cases, coordinate with Benefits and legal teams, and seek improvements in processes and reporting while balancing employee advocacy with policy requirements.

Qualifications

• 3+ years in HR Operations, Employee Services, Global Mobility, or related People function.
• Experience handling sensitive, multi-stakeholder cases with confidentiality.
• Ability to explain policies clearly with empathy and professionalism.

Responsibilities

• Serve as the primary case owner for Global Mobility, Immigration, and Leave Support requests from intake through resolution.
• Guide employees and managers through mobility, immigration, and leave processes with clear timelines and requirements.
• Manage case milestones, SLAs, and reporting within Workday, JustAsk, and other platforms.
• Own the employee-facing experience for sensitive cases and coordinate handoffs with Benefits and SMEs.
• Escalate complex policy or legal matters to appropriate teams while staying the main employee contact.
• Identify recurring questions and contribute to process improvement and automation.

Skills

Case management

Multistakeholder coordination

Empathetic communication

Workday experience

JustAsk experience

Education

Bachelor's degree in HR

Tools

Workday

JustAsk

Job description

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

What you’ll do as an Employee Support Specialist

• Serve as the primary case owner for Global Mobility, Immigration, and Leave Support requests from intake through resolution, giving employees proactive communication throughout the lifecycle of each case.
• Guide employees and managers through global mobility, immigration, and leave processes by clearly explaining eligibility, timelines, documentation requirements, expectations, and next steps.
• Manage case milestones, documentation, service level agreements, and reporting within Workday, JustAsk, and other case management platforms while maintaining accurate and timely case records.
• Own the employee-facing experience for sensitive, compliance-driven cases, coordinating handoffs with the Benefits Team and other subject matter experts while maintaining ownership of employee communication and case management.
• Escalate complex policy, compliance, accommodation, or legal matters to the appropriate teams while remaining the primary point of contact for the employee.
• Identify recurring employee questions and opportunities for process improvement and automation, contributing to knowledge management, reporting, and operational efficiency.

What you’ll bring

• At least 3 years of experience supporting Human Resources Operations, Employee Services, Global Mobility, Immigration, Benefits, Leave Administration, Employee Relations, or a related People function.
• Experience managing sensitive, complex, multi-stakeholder employee cases while delivering a high level of employee support and managing multiple priorities, confidentiality, and service level commitments.
• Working knowledge of Global Mobility and Immigration processes and/or Leave of Absence programs, including the Family and Medical Leave Act, Americans with Disabilities Act, disability, state leave, and paid leave programs; experience supporting both areas is preferred.
• The ability to explain complex policies and processes clearly, empathetically, and professionally while balancing employee advocacy with policy and compliance requirements.
• Strong collaboration and communication skills with the ability to partner effectively across Benefits, Payroll, Human Resources Business Partners, Legal, managers, immigration counsel, vendors, and third-party administrators.
• Experience using Human Resources information systems and case management platforms, such as Workday and JustAsk, to maintain accurate records and generate reporting, along with strong organizational skills, analytical thinking, and a continuous improvement mindset.

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.