Employee Support Specialist

Canada
Remote
Posted Aug 14, 2026
1 position

Opens an external site

Employment type: Full-time
Experience level: Mid-level · 3+ years
Posting language: English
Working hours: 40 hours per week

Job summary

The Employee Support Specialist manages complex, multi-step employee cases related to global mobility, immigration, and leave support. They serve as the primary point of contact, guiding employees through processes while collaborating with cross-functional teams to ensure timely resolution.

Job details

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 an Employee Support Specialist, you’ll own complex, multi-step employee cases that require end-to-end case management, specialized knowledge, and a high-touch employee experience. You’ll focus your time across Global Mobility and Immigration and Benefits Leave Support, serving as the primary employee-facing case owner across both specialties. You’ll guide employees and managers through complex processes while partnering closely with Human Resources, Benefits, Payroll, Legal, Immigration Team, third-party administrators, vendors, and other cross-functional partners to drive timely resolution and a seamless employee experience. 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. #LI-SG2 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.

What you’ll do

Requirements

Candidates must have at least 3 years of experience in HR operations, global mobility, or leave administration. Proficiency in HR information systems and the ability to manage sensitive, multi-stakeholder cases with high attention to compliance are required.