PENN Entertainment, Inc. is North America’s leading provider of integrated entertainment, sports content, and casino gaming experiences. From casinos and racetracks to online gaming, sports betting and entertainment content, we deliver the experiences people want, how and where they want them.
We’re always on the lookout for those who are passionate about creating and delivering cutting-edge online gaming and sports media products. Whether it’s through Hollywood Casino, theScore Bet Sportsbook, or theScore media app, we’re excited to push the boundaries of what’s possible. These state-of-the-art platforms are powered by proprietary in-house technology, a key component of PENN’s omnichannel gaming and entertainment strategy.
When you join PENN Entertainment’s digital team, you’ll not only work on these cutting-edge platforms through theScore and PENN Interactive, but you’ll also be part of a company that truly cares about your career growth. We’re committed to supporting you as you expand your skills and explore new opportunities.
With locations throughout North America, you can build a future at PENN Entertainment wherever you are. If you want to challenge conventions in gaming, media and entertainment, we want to talk to you.
About the Role & Team
We're looking for an CX Manager, AI Optimization to lead the evolution of our customer support experience through AI, automation, knowledge management, and platform optimization. In this role, you'll own the strategy and execution of our support technologies—including Zendesk and AI-powered tools—while identifying opportunities to streamline operations, improve self-service, and empower both customers and agents. Working cross-functionally with Product, Operations, and other business partners, you'll drive scalable solutions, optimize support workflows, and ensure our knowledge ecosystem evolves alongside our products and customer needs.
About the Work
- Lead the strategy, implementation, and ongoing optimization of Customer Support AI and automation initiatives, including chatbot and agent-assist (CoPilot) functionality, to drive improved customer outcomes, operational efficiency, and self-service adoption.
- Administer and optimize the Zendesk Support platform, including workflows, automations, integrations, permissions, and system enhancements.
- Analyze customer journeys, support workflows, internal tools, and product experiences to identify improvement opportunities and implement scalable solutions that enhance both customer and agent experiences.
- Lead the monitoring of performance metrics and user feedback to evaluate the effectiveness of AI, knowledge management, and support operations, using insights to drive continuous improvement.
- Support and guide team members contributing to AI bot improvement and optimization on their tasks and priorities.
- Own the vision and continuous evolution of Operations knowledge management, including internal knowledge bases and external Help Centers, ensuring content remains accurate, accessible, and aligned with evolving products and policies.
- Partner with cross-functional stakeholders to develop, maintain, and govern Standard Operating Procedures (SOPs), knowledge assets, and training materials that support operational excellence.
- Serve as a subject matter expert and advocate for AI adoption, knowledge management, and support platform best practices across the Customer Experience organization.
About You
- 4+ years of experience in Customer Experience, Customer Support Operations, CX Systems, Product Management, or a related field.
- 2+ years of experience administering and optimizing customer support platforms, including configuring workflows, automations, and support technologies.
- Experience implementing or managing AI-powered customer support solutions, including chatbots, agent-assist tools, workflow automation, and knowledge recommendation systems, with a working knowledge of Large Language Models (LLMs) and their application in customer support.
- Proven ability to lead cross-functional initiatives, manage competing priorities, and influence stakeholders while delivering scalable operational improvements.
- Strong analytical, technical, and problem-solving skills, with experience leveraging customer feedback, operational metrics, and reporting to identify opportunities and drive measurable improvements.
- Demonstrated experience creating and maintaining operational documentation, including Standard Operating Procedures (SOPs), internal knowledge bases, customer-facing Help Centers, and training materials.
- Proficiency with customer support technologies, documentation systems, reporting tools, and project management platforms within a B2C environment.
- Experience with leading others in a Customer Service environment
Nice To Have
- Experience with Zendesk AI (Ultimate AI and CoPilot), Salesforce AgentForce, AWS Connect, or similar AI-enabled customer support technologies.
- Experience with conversational design, chatbot administration, customer journey mapping, or product management methodologies.
- Experience evaluating and implementing third-party CX technologies, managing vendor relationships, and/or working within highly regulated industries such as gaming or financial services.
What We Offer
- Competitive compensation package
- Fun, relaxed work environment
- Education and conference reimbursements.
#LI-REMOTE
Penn Interactive is proud to be an equal opportunity workplace. We will consider all qualified applicants for employment without regard to race, color, religion, age, sex, sexual orientation, gender identity, national origin, disability, veteran status, genetic information, or any other basis protected by applicable law.Base pay is one part of the Total Rewards that Penn Interactive provides to compensate and recognize employees for their work. Most sales positions are eligible for a Commission under the terms of an applicable plan, while most non-sales positions are eligible for a Bonus. Additionally, Penn Interactive provides best-in-class benefits to eligible employees. We believe that benefits should connect you to the support you need when it matters most, and should help you care for those who matter most. That’s why we provide an array of options, expert guidance and always-on tools, that are personalized to meet the needs of your reality – to help support you physically, financially and emotionally through the big milestones and in your everyday life.
Skills Required
- 4+ years of experience in Customer Experience, Customer Support Operations, CX Systems, Product Management, or a related field
- 2+ years administering and optimizing customer support platforms, configuring workflows, automations, integrations, and permissions
- Experience implementing or managing AI-powered customer support solutions (chatbots, agent-assist, workflow automation, knowledge recommendation) with working knowledge of LLMs
- Proven ability to lead cross-functional initiatives, manage competing priorities, and influence stakeholders
- Strong analytical, technical, and problem-solving skills; experience using customer feedback and operational metrics to drive improvements
- Experience creating and maintaining operational documentation, SOPs, internal knowledge bases, customer-facing Help Centers, and training materials
- Proficiency with customer support technologies, documentation systems, reporting tools, and project management platforms in a B2C environment
- Experience leading others in a Customer Service environment
- Experience with Zendesk AI (Ultimate AI and CoPilot), Salesforce AgentForce, AWS Connect, or similar AI-enabled customer support technologies
- Experience with conversational design, chatbot administration, customer journey mapping, or product management methodologies
- Experience evaluating and implementing third-party CX technologies, managing vendor relationships, or working in regulated industries (gaming/financial services)
What We Do
Penn Interactive (PI) is an interactive gaming company headquartered in Philadelphia with offices in Las Vegas, NV and Cherry Hill, NJ. As the digital arm to Penn National Gaming (NASDAQ: PENN), the largest regional casino operator in the U.S., we are poised for fast-paced growth in the sports betting and online casino space. We have recently partnered with Barstool Sports to create a unique and exciting sports betting experience through our retail books and the Barstool Sportsbook mobile app.
