Assistant Manager, Training and Escalations

Rush Street Interactive•New Jersey, NJ

11d•$70,000 - $80,000•Hybrid

About The Position

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.

Requirements

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
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 1+ day per week

Nice To Haves

Familiarity with iGaming, online casino, or sportsbook operations is a plus
Occasional travel may be required

Responsibilities

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
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