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Trading Operations Associate - Evenings & Weekends

Penn Interactive · Canada, Remote · Remote

Pay: CAD 50,000 – 65,000 a year

Posted Sep 23, 2026

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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 and Team Our Risk and Trading Operations team is available 24/7 to assist the various functions in the department (Trading/Marketing/Customer Support/etc.) in troubleshooting and escalating issues on all our operational sports betting platforms.This team is critical in ensuring the Risk & Trading department consistently delivers one of its core goals of “operational excellence”. About the Work Assist Traders with identifying, documenting, and escalating issues within the team Support verification, adjustment & creation of Sport & Competition setups across environments Help test and monitor app features to ensure proper functionality and navigation Contribute to Compliance checks, market submissions, and post-release testing Communicate with data providers and support ticketing Daily review of betting content Monitoring pre-game and in-play markets Cross-functional assignments with Compliance, Marketing & Product Assist Customer Experience with issue resolution Other duties as assigned About You Post-secondary degree, or equivalent work experience Must be able to work weekends, evenings and holidays Extensive sports knowledge, particularly with regards to the four major professional sports leagues; esports knowledge considered an asset Sports betting knowledge & experience would provide added value Clear and effective communication skills Must be computer savvy Experience using iPhone and Android devices What We Offer Competitive compensation package Comprehensive Benefits package Fun, relaxed work environment Education and conference reimbursements #LI-REMOTE Salary Range $50,000 — $65,000 CAD Penn Interactive is proud to be an…