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Posted 4 months ago

Director of Player Development

@ Penn Interactive

Toronto, Ontario

5+ years experience
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SIGNALS

Overview

Penn Interactive is hiring a Director of Player Development to own VIP performance across its online sportsbook and iCasino products in an assigned regional territory. The role directly oversees all VIP Managers in that region, drives VIP acquisition, retention and revenue, and reports KPIs to the Vice President of VIP. The posting states a remote arrangement and a salary range of $140,000 to $160,000 CAD.

Responsibilities:

  • Oversee VIP performance across online sportsbook and iCasino products in a region
  • Directly manage and develop all regional VIP Managers
  • Drive VIP acquisition, retention, P&L and market share growth
  • Report KPIs and manager performance to the Vice President of VIP
  • Monitor competitor VIP offerings and maintain product knowledge

Requirements summary:

  • 5+ years of gaming experience, online or brick-and-mortar
  • 3+ years of management experience leading a sales team
  • 2+ years of experience with an online gaming operation
  • Strong Excel, data management and communication skills
  • Passion for sports, casino and sports betting

Tools & skills

Source and dates

Employer career site / ATS feed · greenhouse

Employer posting date
2026-07-21
First seen by our source
2026-10-08
Source record updated
2026-10-10

These dates describe the source record, not a live verification that the employer is still hiring. Check the original posting.

Job details

SeniorityDirector
DepartmentBusiness operations
Experience5+ years
Management experience3+ years
Manages peopleYes
Travelair: moderate
Work settingHome, Office, Client sites
PositionMostly sitting
Physical demandsphysical low · computer high
Perks mentionedPerformance bonus

Summary and details written by AI from the posting; the employer’s posting is the authority.

Penn Interactive

FieldValue
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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

Ownership and oversight of Player Development performance across all offered online sportsbook and iCasino products for all operating states and provinces within an assigned region (including, but not limited to - VIP acquisition, VIP retention, VIP P&L, VIP reinvestment, VIP market share expansion).

Direct oversight and development of all VIP Managers within all operating states and provinces in an assigned region.

About the Work

  • Directs the casino marketing function for PENN Interactive, focused on iCasino states
  • Drives revenue, increases VIP database, and growth in key markets
  • Leads strategic direction for the regional VIP team to reach key VIP sales metrics, customer engagement, market share, and net revenue
  • Assists with development and enforcement of department processes and compliance initiatives that improve operations, efficiency, and service
  • Provides the Vice President of VIP with high level KPI data reporting and reviews of individual manager, host, and associate performances within an assigned region
  • Consistently keeps a high level of awareness of the VIP market offerings from competitors across the industry and leverages all relevant intel to acquire and maintain VIP wallet share within an assigned region
  • Maintains an updated and high level of knowledge of all relevant details of front-end product and technology (including, but not limited to, new product offerings and releases, cashier options for financial transactions, rules of casino games offered and different bet types on the sportsbook, etc…) and keeps regional staff informed and educated on all relevant information in this aspect
  • Assists with the creation of a steady top of funnel stream for new VIP business by generating opportunities that target relationships with potential high value players and social spaces
  • Oversee all new member welcomes, investigation, loyalty, sales, surveys, and the reactivation of lapsed members within assigned region
  • Utilizes daily reporting and analysis to make sound business decisions for an assigned region
  • Assists the Vice President of VIP with the creation, implementation and adoption of all new department initiatives and policies, including, but not limited to - sales performance incentive programs for the entire regional team as well as individual employees within an assigned region
  • Maintains constant and open communication with the Risk and Trading team, Responsible Gaming, Payment, and AML teams to make informed decisions as needed based on business

About You

  • At least 5+ years of gaming experience either online or with a brick-and-mortar casino
  • At least 3+ years of management experience, with a proven track record of successfully managing a sales team and driving revenue
  • At least 2+ years of experience with an online gaming operation
  • Proven experience in online gaming, customer service, concierge, luxury telemarketing or other account management
  • Excellent computer skills with an emphasis on Excel, excellent communication skills and telephone etiquette
  • Proficient in data management tools
  • Positively affects interactions with customers and employees, and has the resiliency to deal with difficult customers in all business conditions
  • Ability to develop, review, and comprehend player tracking screens, reports, and all other necessary information and documentation
  • Ability to communicate effectively with external contacts and all levels of
  • The ability to travel and attend both on and off property events throughout the United States and Canada
  • Oversee and supervise high level events designed for our top customers and oversee team members at said events
  • Must be able to qualify for licenses and permits required by federal, state and local regulations
  • MUST HAVE: Passion for sports, casino and/or sports & casino betting

#LI-REMOTE

Salary Range

$140,000—$160,000 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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