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Office Manager and Administrative Assistant

Chicago

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

Executive Assistant Support

  • 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

What You'll Bring:

  • 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 
This role spans a wide breadth of experience at Rush Street Interactive, welcoming candidates with diverse experiences, backgrounds, and locations. The pay range reflects potential variations in experience, skills, and location. The pay range does not reflect total compensation, which includes base pay, benefits, and/or bonuses. For candidates outside the US (Canada, Europe, Latin America), we take a locally informed approach to compensation and will share specific ranges based on your country of residence.

Location Eligibility (for nationwide roles): Open to candidates across the U.S.

Location Eligibility (for other roles): Location requirements may vary and will be specified in the job posting.

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, and vision insurance
  • Paid Time Off (Eligibility Varies by Role)
  • Employee Assistance Program (EAP)

Pay Range

$70,000 - $75,000 USD

What Makes Us Great:
  • 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

As a rapidly growing company in an emerging industry, you’ll have a huge impact on our product and our company. We like proactive team members and strive to have a company of self-disciplined professionals who enjoy collaboration, having fun, and of course, achieving together what others believe to be improbable. We are dedicated to treating everyone with respect and to support your professional and personal growth.

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.

Be at the forefront of this ground-breaking industry! Apply now!

Rush Street Interactive uses AI-assisted tools at select stages of the hiring process to enhance efficiency, consistency, and communication. AI does not make hiring decisions - final decisions are made exclusively by our recruiting and hiring teams.

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