Senior Legal Counsel, Chicago, IL

Rush Street Interactive (NYSE: RSI) is a market leader in online casino and sports betting, currently operating real-money gaming with our brands: , , and  We’re building bridges between online, social and land-based gaming businesses to create amazing, integrated experiences that keep players in the game.

The Senior Legal Counsel will serve as a trusted legal advisor on all aspects of employment law, providing strategic and practical guidance to support the company’s global workforce. This role will partner closely with the People team and business leaders to address employment matters across the employee lifecycle, including contracts, compliance, workplace policies, investigations, and disputes.

The ideal candidate will bring deep expertise in U.S. labor and employment law, as well as significant experience advising multinational companies with global operations and work forces. This includes partnering with local counsel across multiple jurisdictions to ensure compliance with diverse legal frameworks and supporting cross-border employment initiatives. The successful candidate will demonstrate sound judgment, cultural fluency, and the ability to deliver clear, business‑oriented legal solutions in a fast‑paced, international environment.

• Provide counsel on a broad range of domestic and international employment law matters, including but not limited to employment agreements, disputes, regulatory compliance, workforce planning, workplace investigations, performance management, disciplinary actions and terminations.
• Advise on employment issues arising in Latin America and European jurisdictions, ensuring compliance with local employment laws and requirements.
• Draft, review and maintain employment‑related agreements, workplace policies, and handbooks in compliance with applicable local and regional regulations.
• Conduct compliance reviews to ensure adherence to employment regulations and internal company policies.
• Partner with the People team to develop and implement globally consistent yet locally compliant employment practices, risk mitigation strategies, and employee relations processes.
• Manage engagement with external employment counsel worldwide, ensuring efficient, coordinated, and cost‑effective delivery of specialized advice.
• Support manager development by coaching on risk mitigation and employment practices, including performance management, documentation, and termination processes.
• Collaborate with internal stakeholders on cross‑border transactions and workforce integration initiatives.

• Juris Doctor (J.D.) or equivalent law degree from an accredited institution.
• Must be licensed to practice in one or more U.S. jurisdictions.
• 6+ years of experience practicing labor and employment law.
• Strong legal research, writing, and analytical skills with a global mindset.
• Proven ability to provide practical, business‑oriented advice in complex, multi‑jurisdictional environments.
• Demonstrated experience working with or within international organizations, preferably with exposure to LATAM and EU employment law frameworks.
• Effective communicator with the ability to explain complex legal concepts clearly to non‑legal stakeholders.
• Highly organized, with strong prioritization skills and the ability to manage multiple projects simultaneously in a fast‑paced environment.
• Collaborative mindset with the ability to work both independently and as part of a broader legal team.
• Interest or experience in privacy, data protection (including GDPR), and intellectual property law is a plus.
• Familiarity with legal technology tools is a plus.
• Proficiency in Spanish is a plus but not required.
• Able to travel occasionally both domestically and internationally. #LI‑REMOTE

Open to candidates across the U.S. (except California, Washington, Maryland, and New York).

Location requirements may vary and will be specified in the job posting.

• Discretionary annual company bonus (Eligibility Varies by Role)
• 401(k) plan with 100% company match on the first 4%
• Comprehensive medical coverage (HSA & FSA plans), dental, and vision insurance
• Pai…