IT Systems and Application Manager

Rush Street Interactive (NYSE: RSI) is a market leader in online casino and sports betting, currently operating real-money gaming with our brands: , , and We're building bridges between online, social and land-based gaming businesses to create amazing, integrated experiences that keep players in the game.

The IT Systems and Applications Manager is responsible for leading a team of IT Systems Engineers while maintaining hands-on involvement in the management and optimization of enterprise SaaS applications. This player/coach role balances people management, mentorship, and technical execution. You will oversee vendor relationships, drive application strategy, and ensure IT systems and services support a global, remote workforce. Your primary focus will be delivering a reliable, secure, and seamless technology experience for all employees while developing your team's capabilities and ensuring alignment with organizational goals. 

What You'll Do:

• Lead, mentor, and develop a team of IT Systems Engineers, providing coaching, performance feedback, and career development guidance. 
• Maintain hands-on involvement in the administration and optimization of enterprise SaaS applications, balancing managerial duties with technical contributions. 
• Manage vendor relationships for enterprise applications, including contract oversight, service level monitoring, and escalation management. 
• Partner with the Sr Director of IT to develop and support the annual IT budget, providing input on resource needs, licensing costs, and technology investments. 
• Oversee the administration of Microsoft 365 services including SharePoint, Exchange Online, Intune, and Entra ID, ensuring optimal configuration and user experience. 
• Establish and maintain governance frameworks for enterprise applications, ensuring alignment with organizational objectives, security requirements, and compliance standards. 
• Drive standardization and process improvement across application management, focusing on operational efficiency and service quality. 
• Act as an escalation point for complex technical issues, working alongside the team to ensure timely resolution. 
• Ensure IT services support a distributed, remote workforce across multiple time zones, maintaining consistent availability and responsiveness. 
• Collaborate cross-functionally with other departments, Development teams, Infrastructure team, and external vendors to deliver integrated technology solutions. 
• Ensure compliance with relevant regulations and standards (e.g., GDPR, ISO-27001, PCI-DSS) across all jurisdictions the organization operates in. 
• Create and maintain documentation for application configurations, processes, and team procedures. 
• Lead the evaluation, selection, and implementation of new enterprise applications as business needs evolve. 

What You'll Bring:

• Bachelor's Degree or an equivalent combination of education and experience 
• 3+ years of experience managing IT staff, including coaching, performance management, and team development. 
• 7+ years of experience implementing and administering Microsoft 365 (Exchange, SharePoint, Intune, Entra ID) and Azure environments. 
• Certified on M365 management and administration, Azure. 
• Proven experience managing and administering enterprise SaaS applications in a corporate environment. 
• Strong understanding of application lifecycle management, vendor management, and IT service delivery. 
• Excellent interpersonal and leadership skills, with the ability to motivate and develop team members. 
• Strong written and verbal communication skills, with an ability to communicate effectively with technical and non-technical stakeholders. 
• Experience working in an organization with a globally distributed, remote workforce. 
• Critical thinking skills with the ability to prioritize, make decisions, and manage competing demands. 
• A sense of ownership, accountability, and a collaborative approach to problem-solving. 
• Experience and certified on modern Identity and Access Management Systems, preferred. 
• Experience with ISO 27001 controls and PCI DSS requirements, preferred. 
• Experience with developing and implementing IT processes and governance frameworks, preferred.  
• Experience working with the ITIL Framework, preferred.  
• Able to travel occasionally both domestically and internationally.

In this position, you may be required to obtain and maintain a license with one or more gaming regulatory agencies. It is a requirement of this position that you meet the relevant eligibility requirements, and you are eligible to obtain and hold such license at all times of your employment, whether you apply or not. #LI-REMOTE 

Location Eligibility (for nationwide roles): Open to candidates across the U.S. (except California, Washington, Maryland, and New York).

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

$80,000 - $120,000 CAD

• 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.

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