Director, Product Management, Core Products

PI Director, Product Management, Core Products
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Penn Interactive
Salary: CA$185K – CA$230K per year
Canada only

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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 & TeamWe 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.

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.

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About the job
Apply before
Nov 17, 2026
Posted on
Sep 18, 2026
Job type
Full Time
Experience level
Director

Salary

Salary: CA$185K – CA$230K per year

Experience

8 years minimum

Location requirements
Suggest an edit

Canada

Hiring timezones
Show UTC offsets

Canada +/- 0 hours

Job categories
Director Of Product Management Product Leadership Trust and Safety Product Payments Product Internal Tools Product Management Director Product Management Senior Director Product Management Senior Director Of Product Management Product Management Director Director of Product Senior Director Of Product Senior Director Product Senior Product Director

Skills
Identity and Authentication Authentication KYC Payments Fraud Prevention Compliance Responsible Gaming Internal Tools APIs Platform Architecture Third Party Integrations Data Analytics Analytics Online Gaming Risk Management Trust and Safety Product Management Payment Fraud Customer Support Fintech

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About Penn Interactive

Learn more about Penn Interactive and their company culture.

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Apply now
Job expired?

Please let Penn Interactive know you found this job on Himalayas. This helps us grow!
Apply now

About the job
Apply before
Nov 17, 2026
Posted on
Sep 18, 2026
Job type
Full Time
Experience level
Director

Salary

Salary: CA$185K – CA$230K per year

Experience

8 years minimum

Location requirements
Suggest an edit

Canada

Hiring timezones
Show UTC offsets

Canada +/- 0 hours

Job categories
Director Of Product Management Product Leadership Trust and Safety Product Payments Product Internal Tools Product Management Director Product Management Senior Director Product Management Senior Director Of Product Management Product Management Director Director of Product Senior Director Of Product Senior Director Product Senior Product Director

Skills
Identity and Authentication Authentication KYC Payments Fraud Prevention Compliance Responsible Gaming Internal Tools APIs Platform Architecture Third Party Integrations Data Analytics Analytics Online Gaming Risk Management Trust and Safety Product Management Payment Fraud Customer Support Fintech

Browse similar jobs
Remote Director Director-Of-Product-Management Jobs Remote Full Time Director-Of-Product-Management Jobs Remote Director Director-Of-Product-Management Jobs in Canada Remote Full Time Jobs in Canada Remote Director-Of-Product-Management Jobs in Canada

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