Assistant Manager, Training and Escalations

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.
The Assistant Manager, Training & Escalations is a dual-function leadership role responsible for overseeing Player Support training programs and the Escalations function. This role drives both the strategic direction and execution of training initiatives while ensuring the Escalations team delivers high-quality, efficient, and compliant resolutions.
The position leads onboarding and continuous education for Player Support Agents, ensuring readiness and long-term performance, while also supporting escalation processes, team effectiveness, and operational improvements. This role partners cross-functionally to align training, quality assurance, and escalation insights with business needs.
What You'll Do:
Training Leadership:
Own the full lifecycle of Player Support training programs, including new hire onboarding, continuing education, and curriculum updates for all Player Support Agents and support team members
Design, build, and maintain training materials including 1Huddles, training roadmaps, knowledge assessments, process guides, and multimedia learning content in Guru and other platforms
Lead and manage the Training team, including Training Specialists and Training Specialist, ensuring effective facilitation, curriculum ownership, and day-to-day execution
Oversee new hire adherence to the 90-day Foundational Period, monitoring performance benchmarks, assessment scores, attendance, and behavioral expectations as defined in the Foundational Period
Actively performance manage new hires who are not meeting Foundational Period expectations, delivering structured coaching, documented feedback, and escalating when necessary
Partner with QA and operational leadership to proactively identify knowledge gaps, workflow breakdowns, and agent decision-making trends, translating those insights into targeted training improvements
Ensure all training content stays aligned with current processes, product updates, regulatory requirements, and iGaming operational standards
Drive data-informed improvements to training efficacy using assessment results, QA scores, and early tenure performance indicators
Collaborate cross-functionally with QA, Escalations, and Player Experience leadership to ensure training priorities reflect business and operational needs
Escalations Leadership
Oversee the Escalations team in partnership with Escalations Leads, ensuring agents are delivering complex case resolution with quality, accuracy, and efficiency
Support Escalations Leads in day-to-day team management, coaching, and performance oversight of Escalations Agents
Ensure Escalations team processes and procedures are current, well-documented, and consistently followed, identifying and driving updates as workflows, products, or regulatory requirements evolve
Proactively identify opportunities for the Escalations team to add greater value to players, whether through expanded scope, improved resolution pathways, or new engagement channels
Maintain alignment between the Escalations and Training functions, ensuring Escalations-driven insights feed back into training content and agent development
Monitor Escalations team performance metrics, surfacing trends to leadership and supporting continuous improvement efforts
Serve as a point of escalation for complex or sensitive cases requiring leadership judgment
What You'll Bring:
Bachelor’s degree in Business, Communications, Education, or a related field preferred (or equivalent experience)
4+ years of experience in Customer or Player Support, Training, QA, or operational leadership within a contact center or similar environment
Demonstrated experience managing or leading a training function, including designing and delivering training programs, assessments, and development materials
Experience directly managing or overseeing team performance, including coaching, performance documentation, and disciplinary conversations
Strong understanding of contact center workflows, escalation processes, performance management frameworks, and early tenure development
Familiarity with iGaming, online casino, or sportsbook operations is a plus
Proficiency with or ability to quickly learn 1Huddle, Guru, and Salesforce; comfort working across multiple platforms and tools
Ability to analyze performance data, QA trends, and assessment results and translate them into actionable training or operational improvements
Strong written and verbal communication skills with the ability to engage effectively across frontline agents, leads, and senior leadership
Highly organized with strong attention to detail and the ability to manage multiple priorities in a fast-paced, evolving environment
A collaborative, people-first mindset with a genuine investment in agent development and team success
Ability to work in-office at least 2+ day per week
Occasional travel may be required
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—$80,000 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.