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: BetRivers.com, PlaySugarHouse.com, and RushBet.co. 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.

What You'll Do:

Office Management

• 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 #LI-ONSITE #LI-DNP

• 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)

• Comprehensive compensation
• Work-life balance initiatives
• Autonomy - we embrace personal freedom and responsibility
• Creativity - we are open to new ideas of how we can be better
• Growth - we want you to develop personally as well as professionally
• Top-notch professionals who are passionate about what they do
• People-oriented environment and supportive atmosphere