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: , , 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 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.

• 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 1
  
  Huddles, 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

• 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

• 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
• 3+ years of 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…