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 intuitive, detail oriented, reliable, resourceful, thoughtful, trustworthy and have the highest ethical standards.

This Role Is for You Because

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 ensure that your executives can navigate their days seamlessly.

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. This person will need to work from our Chicago headquarters office 2 days per week, and potentially more frequently on an as-needed dependent upon the CEO’s in-person meeting schedule. Advance notice will be provided when additional office attendance is required.
  • 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.

 

All About You: 

 

  • 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.
  • 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.

 

 

What makes us great:

  • Comprehensive compensation
  • Flexible working hours
  • 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.

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

Apply for this Job

* Required
resume chosen  
(File types: pdf, doc, docx, txt, rtf)
cover_letter chosen  
(File types: pdf, doc, docx, txt, rtf)


Voluntary Self-Identification

For government reporting purposes, we ask candidates to respond to the below self-identification survey. Completion of the form is entirely voluntary. Whatever your decision, it will not be considered in the hiring process or thereafter. Any information that you do provide will be recorded and maintained in a confidential file.

As set forth in Rush Street Interactive’s Equal Employment Opportunity policy, we do not discriminate on the basis of any protected group status under any applicable law.

Race & Ethnicity Definitions

If you believe you belong to any of the categories of protected veterans listed below, please indicate by making the appropriate selection. As a government contractor subject to the Vietnam Era Veterans Readjustment Assistance Act (VEVRAA), we request this information in order to measure the effectiveness of the outreach and positive recruitment efforts we undertake pursuant to VEVRAA. Classification of protected categories is as follows:

A "disabled veteran" is one of the following: a veteran of the U.S. military, ground, naval or air service who is entitled to compensation (or who but for the receipt of military retired pay would be entitled to compensation) under laws administered by the Secretary of Veterans Affairs; or a person who was discharged or released from active duty because of a service-connected disability.

A "recently separated veteran" means any veteran during the three-year period beginning on the date of such veteran's discharge or release from active duty in the U.S. military, ground, naval, or air service.

An "active duty wartime or campaign badge veteran" means a veteran who served on active duty in the U.S. military, ground, naval or air service during a war, or in a campaign or expedition for which a campaign badge has been authorized under the laws administered by the Department of Defense.

An "Armed forces service medal veteran" means a veteran who, while serving on active duty in the U.S. military, ground, naval or air service, participated in a United States military operation for which an Armed Forces service medal was awarded pursuant to Executive Order 12985.


Voluntary Self-Identification of Disability

Form CC-305
Page 1 of 1
OMB Control Number 1250-0005
Expires 04/30/2026

Why are you being asked to complete this form?

We are a federal contractor or subcontractor. The law requires us to provide equal employment opportunity to qualified people with disabilities. We have a goal of having at least 7% of our workers as people with disabilities. The law says we must measure our progress towards this goal. To do this, we must ask applicants and employees if they have a disability or have ever had one. People can become disabled, so we need to ask this question at least every five years.

Completing this form is voluntary, and we hope that you will choose to do so. Your answer is confidential. No one who makes hiring decisions will see it. Your decision to complete the form and your answer will not harm you in any way. If you want to learn more about the law or this form, visit the U.S. Department of Labor’s Office of Federal Contract Compliance Programs (OFCCP) website at www.dol.gov/ofccp.

How do you know if you have a disability?

A disability is a condition that substantially limits one or more of your “major life activities.” If you have or have ever had such a condition, you are a person with a disability. Disabilities include, but are not limited to:

  • Alcohol or other substance use disorder (not currently using drugs illegally)
  • Autoimmune disorder, for example, lupus, fibromyalgia, rheumatoid arthritis, HIV/AIDS
  • Blind or low vision
  • Cancer (past or present)
  • Cardiovascular or heart disease
  • Celiac disease
  • Cerebral palsy
  • Deaf or serious difficulty hearing
  • Diabetes
  • Disfigurement, for example, disfigurement caused by burns, wounds, accidents, or congenital disorders
  • Epilepsy or other seizure disorder
  • Gastrointestinal disorders, for example, Crohn's Disease, irritable bowel syndrome
  • Intellectual or developmental disability
  • Mental health conditions, for example, depression, bipolar disorder, anxiety disorder, schizophrenia, PTSD
  • Missing limbs or partially missing limbs
  • Mobility impairment, benefiting from the use of a wheelchair, scooter, walker, leg brace(s) and/or other supports
  • Nervous system condition, for example, migraine headaches, Parkinson’s disease, multiple sclerosis (MS)
  • Neurodivergence, for example, attention-deficit/hyperactivity disorder (ADHD), autism spectrum disorder, dyslexia, dyspraxia, other learning disabilities
  • Partial or complete paralysis (any cause)
  • Pulmonary or respiratory conditions, for example, tuberculosis, asthma, emphysema
  • Short stature (dwarfism)
  • Traumatic brain injury

PUBLIC BURDEN STATEMENT: According to the Paperwork Reduction Act of 1995 no persons are required to respond to a collection of information unless such collection displays a valid OMB control number. This survey should take about 5 minutes to complete.


Our system has flagged this application as potentially being associated with bot traffic. Please turn off any VPNs, clear your browser cache and cookies, or try submitting your application in a different browser. If this issue persists, please reach out to our support team via our help center.
Please complete the reCAPTCHA above.