Director, Product Management, Core Products

Penninteractive; Canada; Remote; CAD 185,000 - 230,000; Full time

Benefits offered by this job

Competitive pay

Relaxed work environment

Education reimbursements

Parental leave top up

Mentoring & progression

Job summary

PENN Entertainment, Inc. is seeking a Director of Product to lead the Core Products organization, owning Identity & Trust, Payments & Fraud, and Internal Tools—overseeing onboarding, KYC, login, compliance, deposits, withdrawals, and internal workflows.

You will set strategy, coach a PM team, and partner with Engineering, Design, Analytics, and Compliance to drive growth and risk management. You will influence senior stakeholders, align on platform architecture, and deliver scalable capabilities

Qualifications

• 8+ years in product management with 2+ years in people leadership.
• Experience leading managers and senior ICs across multiple product areas.
• Track record of translating product strategy into focused roadmaps and measurable outcomes.
• Experience in complex platform domains such as identity, onboarding, payments, fraud, risk, or internal tooling.
• Strong technical fluency and collaboration with engineering on APIs and integrations.

Responsibilities

• Define and drive the product strategy and roadmap for Core Products (Identity & Trust, Payments & Fraud, Internal Tools).
• Lead and develop Product Managers and leaders, ensuring clear ownership and accountability.
• Own critical journeys: registration, identity verification, account access, funding, withdrawals, and account management.
• Build shared capabilities connecting digital and retail experiences for online sportsbook and casino businesses.
• Establish KPIs, use data and business impact to prioritize investments and measure outcomes.

Skills

Product leadership

Cross-functional leadership

Strategy development

Data-driven decision making

Executive communication

Job description

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 are looking for a Director of Product to lead our Core Products organization, responsible for the foundational experiences and platforms that enable customers to safely and seamlessly engage with PENN across online gaming and our digital retail experiences. This leader will own a broad portfolio across Identity & Trust, Payments & Fraud, and Internal Tools — including registration and onboarding, KYC, login and account access, compliance and Responsible Gaming, deposits and withdrawals, fraud prevention, and the tools and workflows used by Customer Support, VIP, and operational teams.

You will set the strategy for these areas, lead multiple product teams, and partner closely with Engineering, Design, Analytics, Compliance, Risk, Operations, and business leaders to improve customer experience, drive growth, manage risk, and build scalable capabilities across PENN. You will lead a team of Product Managers, including both managers and individual contributors.

About the Work

• Define and drive the product strategy and roadmap for Core Products across Identity & Trust, Payments & Fraud, and Internal Tools.
• Lead, coach, and develop Product Managers and product leaders, creating clear ownership and accountability across the portfolio.
• Own critical customer journeys including registration, identity verification, account access, funding, withdrawals, and account management.
• Build shared capabilities that support PENN’s online Sportsbook and Casino businesses and increasingly connect our digital and retail customer experiences.
• Improve payment performance and customer funding experiences while partnering with Fraud and Risk teams to protect customers and the business.
• Partner with Compliance and Responsible Gaming teams to build regulatory and customer‑protection requirements into intuitive product experiences.
• Modernize internal tools and workflows for Customer Support, VIP, Fraud, Compliance, and Operations, reducing manual work and improving how teams serve customers.
• Establish clear KPIs and use customer insights, data, and business impact to prioritize investments and measure outcomes.
• Partner deeply with Engineering to make thoughtful decisions around platform architecture, scalability, reliability, and third‑party integrations.
• Influence and align senior stakeholders across Product, Engineering, Design, Analytics, Operations, Compliance, Legal, Finance, and our business teams.
• Other duties as required.

About You

• 8+ years’ experience in product management, plus 2+ years of people leadership experience is required.
• Experience managing managers and senior individual contributors across multiple product areas.
• Experience setting product strategy and translating it into focused roadmaps and measurable outcomes.
• Experience in one or more complex platform domains such as identity, authentication, onboarding, KYC, payments, fraud, risk, trust & safety, compliance, or internal tooling.
• Strong technical fluency and experience partnering with Engineering on platforms, APIs, integrations, and complex technical systems.
• Strong analytical judgment and experience using data to identify opportunities, prioritize investments, and measure business impact.
• Demonstrated ability to balance customer experience, growth, risk, regulatory requirements, and operational needs.
• Strong cross‑functional leadership and executive communication skills.
• Experience operating in complex, regulated, high‑transaction, or multi‑product environments.
• Experience in online gaming, fintech, financial services, marketplaces, commerce, or other regulated digital businesses is a plus.

What We Offer

• Competitive compensation package.
• Fun, relaxed work environment.
• Education and conference reimbursements.
• Parental leave top up.
• Opportunities for career progression and mentoring others.

#LI-REMOTE

Salary Range

• $185,000 — $230,000 CAD

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.