Office Manager and Executive Assistant

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.

Rush Street Interactive is seeking a highly organized, proactive Office Manager & Executive Assistant to support our Chicago office and Executive Leadership Team (ELT). This is a unique hybrid role that blends office operations, employee experience, and executive support, serving as a central point of coordination for the Chicago office while enabling executive productivity.

You’ll play a critical role in ensuring a seamless, well‑run, and engaging office environment, while also acting as a trusted partner to senior leaders, helping them operate efficiently and focus on strategic priorities.

This role is onsite 5 days per week.

• Own the day‑to‑day operations of the Chicago office, ensuring a professional, organized, and welcoming environment
• Manage office vendors, supplies, facilities coordination, and maintenance requests
• Partner with People Operations on onboarding, offboarding, and in‑office employee experience initiatives
• Coordinate office logistics including mail, badges, visitor management, and workspace readiness
• Plan and support in‑office events, leadership visits, and team gatherings
• Ensure adherence to office policies, safety standards, and compliance requirements
• Plan team outings and events to encourage office attendance

• Provide calendar management, scheduling, and travel coordination for the Executive Leadership Team (excluding the CEO)
• Coordinate meetings, offsites, and leadership events, both domestic and international travel, ensuring strong organization and follow‑through
• Prepare meeting materials, agendas, and assist with follow‑ups as needed
• Support expense management and administrative tasks
• Act as a trusted partner to executives, maintaining a high level of discretion and professionalism
• Partner closely with the Executive Assistant to the CEO to ensure consistency in executive support
• Collaborate with People Operations, Finance, and IT to support office operations and employee experience

• 2+ years of experience in office management, executive support, or a similar hybrid role
• Strong organizational and time management skills with the ability to manage multiple priorities
• Experience in calendar management, preferably in Outlook
• Excellent communication and interpersonal skills
• Proactive, solutions‑oriented mindset with strong attention to detail
• Ability to work independently and take ownership in a fast‑paced environment
• Experience coordinating events and travel
• Must be in downtown Chicago office 5 days per week

Open to candidates across the U.S. Must be in downtown Chicago office 5 days per week.

• 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
• Paid Time Off (Eligibility Varies by Role)
• Employee Assistance Program (EAP)

$60,000—$70,000 USD

Rush Street Interactive is an equal opportunity employer and committed to a diverse and inclusive workplace. All qualified applicants will be considered for employment without regard to race, national origin, ancestry, sex, sexual orientation, sexual identity and expression, marital status, family status, lifestyle, age, culture, religion, military and veteran status, citizenship, or disability.