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.

As Executive Assistant, you will work out of our Chicago headquarters on a hybrid basis and report directly to the CEO. Successful candidates will be self-starters who are responsive and excel in a fast-paced environment. The ideal candidate will be proactive, problem solving, intuitive, detail oriented, reliable, resourceful, thoughtful, trustworthy and have the highest ethical standards.  

Who Are You:

You are a motivated self-starter, capable of working independently with minimal direction and supervision. You thrive in providing administrative support within a fast-paced environment. Demonstrating a high level of judgment and discretion, particularly concerning confidential information, comes naturally to you. Your interest in connecting the dots and anticipating needs to ensures that your executives can navigate their days seamlessly. You continuously seek new ways to improve operations and provide added value.  

What You'll Do:

• Provide direct administrative assistance to the company’s CEO and offer general support to the company’s Executive Leadership Team and Chicago office. 
• Efficiently manage the CEO's schedule, prioritizing appointments and meetings to ensure critical matters receive appropriate attention. 
• Coordinate domestic and international travel arrangements, including transportation and hotel accommodations, create detailed travel itineraries, and ensure the validity of all visas and passport information; manage and maintain calendars. 
• Assist in creating presentations for various team meetings and generate ad hoc reports as requested. 
• Organize both onsite and offsite meetings
• Act as a liaison between the CEO, Executive Leadership Team, Senior Leadership Team and other business contacts 
• Support event planning activities both locally and internationally as required. 
• Complete expense reports, purchase orders, and contracts, manage corporate card purchases, and participate in budget planning and tracking as necessary. 
• Oversee general office management duties, including inventory management, documents signed/notarized, and visitor registration facilitation. 
• Provide clerical support and assist with miscellaneous administrative functions, such as managing incoming and outgoing mail, contracts, processing invoices, and expenses.
• Savvy with IT to address support issues. 
• Undertake additional special projects as needed.
• Provide personal assistance, including but not limited to booking personal travel, booking restaurants, scheduling medical appointments, and handling ad-hoc personal tasks to support the CEOs needs.
• Facilitate support for visitors to the office, including team members and external guests. Responsibilities include greeting visitors, arranging visitor passes, ensuring access to necessary IT equipment, coordinating catering, booking meeting rooms and restaurants.  
• Oversee email management for the CEO, including monitoring inboxes, prioritizing communications, drafting and responding to emails and ensuring timely follow-up on key correspondence. 
• Proactively identify opportunities to enhance CEO’s efficiency and daily workflow by suggesting new ideas, streamlining processes and effective solutions to challenges as they arise.  

What We're Looking for:

• High school degree or equivalent required
• Bachelor's Degree or professional work experience
• 5+ years’ experience in administrative environment with Executive Assistant (EA) or equivalent experience
• 5+ years' experience with Windows desktop computer applications: Word, Excel, PowerPoint and Microsoft Team and collaborative tools.
• 5+ years' experience core competency in managing executive travel, email, calendar, and contact list, budget and expenses. 
• Exceptional communication, organizational, and time management skills. 
• Extensive experience in Microsoft Outlook, Word, Excel, PowerPoint 
• Ability to effectively manage multiple projects simultaneously, meeting deadlines consistently. 
• Strong interpersonal skills with the ability to communicate effectively to people of different backgrounds and levels of experience. 
• Proven understanding of executive support, including managing calendars and inboxes, travel arrangements and high-level communications.
• This person will be required to work from our Chicago headquarters office two days per week
• Additional office attendance may be required based on the CEO’s in-person meeting schedule.
• Advance notice will be provided when additional office attendance is needed. #LI-HYBRID

• 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 doing
• 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.

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