Office Manager and Administrative Assistant

Rush Street Interactive•Chicago, IL

6h•Onsite

About The Position

Rush Street Interactive (NYSE: RSI) is a market leader in online casino and sports betting, currently operating real-money gaming with brands like BetRivers.com, PlaySugarHouse.com, and RushBet.co. The company is building bridges between online, social, and land-based gaming businesses to create integrated experiences for players. Rush Street Interactive is seeking a highly organized, proactive Office Manager & Executive Assistant to support their Chicago office and Executive Leadership Team (ELT). This hybrid role combines office operations, employee experience, and executive support, serving as a central point of coordination for the Chicago office while enhancing executive productivity. The successful candidate will 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.

Requirements

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

Responsibilities

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

Benefits

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 insurance
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
Dedicated to treating everyone with respect and to support your professional and personal growth