Executive Assistant

Full-time - Entry Level

Chicago, IL

About the position

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.

Responsibilities

• 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.

Requirements

• 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.

Benefits

• Discretionary annual company bonus
• 401(k) plan with 100% company match on the first 4%
• Comprehensive medical coverage (HSA & FSA plans), dental, and vision insurance
• Flexible time off plan
• Employee Assistance Program (EAP)