Lead Product Manager, Payments

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, , or 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 The Interactive Product Management team leads the strategy for Penn Interactive's incredible digital product portfolio – from ESPN BET, theScore Bet, theScore Media, and iCasino. This team impacts the way millions of people engage with our products in more personalized and immersive ways, leveraging bleeding-edge technologies. As an enthusiastic and entrepreneurial product leader, you will manage, innovate, and execute on product initiatives that focus on the promotional experience in both ESPN BET and theScore BET. In this role this you will take on challenges in a fast paced ever changing environment. This is a high impact, high visibility role that will impact key features, innovation and scale. It requires strong collaboration, leadership and agility to drive the development of a Tier 1 Sportsbook product.  The right candidate is a seasoned product leader with deep experience in payments infrastructure and fraud prevention. You understand the complexities of transaction flows, risk mitigation, and regulatory compliance, and have successfully built systems that balance security with seamless user experience. You're a strategic thinker, a collaborative partner to engineering, data science, compliance, and operations, and a confident communicator who can influence executive stakeholders.  Payments and fraud systems are foundational to any gaming or sportsbook platform, directly impacting user trust, conversion, and lifetime value. This team’s mission is to deliver reliable, secure, and scalable transaction experiences while proactively identifying and stopping fraud. You’ll help define the roadmap that enables the business to grow responsibly while protecting users and the company from financial and reputational risk.   About the Work  Discover and define product solutions that reduce fraud, optimize payment success rates, and support PENN’s growth and trust objectives, while developing a long-term strategy for scalable, secure infrastructure. Define and report on KPIs related to payment conversion, fraud rates, chargebacks, false positives, and cost of risk. Collaborate closely with compliance, risk, legal, finance, and external partners to ensure systems meet regulatory requirements and industry standards (, KYC, AML, PCI). Leverage quantitative and qualitative insights to guide data-informed prioritization and risk-based decision making. Partner with operations and customer support teams to ensure product solutions translate into real-world improvements in efficiency and customer experience. Maintain transparency and accountability across stakeholders through clear documentation, structured communication, and consistent product updates. Foster collaboration across cross-functional teams including engineering, data science, operations, and fraud/risk teams. Monitor emerging threats, evolving fraud patterns, and the competitive landscape to inform roadmap direction and innovation opportunities. Contribute to the growth of the Product organization by mentoring team members, sharing best practices, and driving operational excellence. Other duties as required.   About You  8+ years of product management experience, with 2+ years in a people leadership role. Deep experience building and scaling payments infrastructure and/or fraud detection systems is required. Experience working on high-volume, consumer-facing platforms with real-time risk and financial exposure is required. Experience in sports betting, online gaming, or highly regulated financial services is highly preferred. Familiarity with KYC, AML, PCI compliance, and fraud prevention methodologies is highly preferred. Proven ability to connect product strategy with business objectives, particularly around reducing loss, increasing trust, and improving conversion. Strong analytical mindset with demonstrated ability to use data to drive decisions and validate assumptions. Results-oriented leader who can inspire, influence, and develop talent in a cross-functional, fast-paced environment. High emotional intelligence with a track record of navigating complex, cross-functional topics with clarity and diplomacy. Exceptional communication skills with the ability to distill complex financial and technical concepts for diverse audiences. Skilled in partnering with engineering to evaluate tradeoffs, unblock challenges, and drive execution at scale. Experience managing and coaching product managers to deliver high-impact results.   What We Offer:  Competitive compensation package Comprehensive Benefits package. Fun, relaxed work environment. Education and conference reimbursements. #LI-REMOTE   Candidates residing in Ontario requiring special accommodation can email