Senior Technical Program Manager, Intelligent Automation

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 In this role, you will  be responsible for  driving automation initiatives that deliver measurable business value across  all of Penn Entertainment . Your work will span the full lifecycle of automation, from  identifying  opportunities to delivering and  optimizing  solutions. While automation is the primary focus, you will also consider AI-supported solutions where they align with the company’s overall AI strategy.  You will partner closely with a small team of RPA specialists, AI strategists, and business leaders to  identify  opportunities, shape solutions, and drive meaningful impact across the organization.

About the Work

• Identify and assess opportunities for automation and process improvement across business units.

• Collaborate with stakeholders to understand pain points, gather requirements, and prioritize initiatives based on business impact.

• Work hands-on with internal development teams and external vendors to design, build, and implement automation solutions.

• Ensure all automation and AI-supported solutions are practical, scalable, and aligned with company objectives and standards.

• Maintain a portfolio of automation initiatives, balancing quick wins with longer-term strategic projects.

• Lead structured discovery sessions and maintain a self-service intake process for automation ideas.

• Evaluate and prioritize opportunities using standardized criteria such as effort, risk, return on investment, compliance, and technical feasibility.

• Oversee the delivery of automation solutions, ensuring clear communication and alignment with internal teams and external partners.

• Manage vendor relationships, including selection, onboarding, and performance tracking for external automation and AI solution providers.

• Collaborate with engineering, data, security, and product teams to ensure seamless integration and operational readiness.

• Define and track key performance indicators such as hours saved, error reduction, cycle-time improvement, compliance, and stakeholder satisfaction.

• Stay informed about emerging automation and AI technologies and recommend new approaches when appropriate.

• Support a culture of continuous improvement and operational excellence across the organization.

• Other duties as required.  

About You

You are a self-motivated professional with a passion for operational efficiency and a proven track record in automation and business process improvement. You thrive on identifying opportunities to eliminate waste and deliver measurable value. You are comfortable working independently, but you also excel at building strong partnerships with internal development teams and external vendors.  

• At least 5 years of experience designing, building, and managing automation solutions (workflow automation, or scripting), with hands-on expertise in at least one leading platform (for example, UiPath or Power Automate).

• Ability to evaluate existing processes and identify opportunities for improvement, increased efficiency, and automation.

• Demonstrated success in delivering business efficiency improvements through automation, with clear examples of measurable impact.

• Experience collaborating with internal engineering or development teams to deliver technical solutions.

• Experience managing relationships with external vendors or solution providers, including selection, onboarding, and performance management.

• Familiarity with evaluating and implementing AI-supported solutions for process improvement, and an understanding of how to align these with a company’s overall AI strategy.

• Strong program management and stakeholder influence skills, with the ability to prioritize initiatives and drive projects to completion.

• Excellent communication skills, able to translate technical concepts into clear business value for both technical and non-technical audiences.

• Experience in regulated or high-scale industries (such as gaming, fintech, or entertainment) is a plus.

• A strategic mindset, a collaborative approach, and a commitment to continuous improvement.  

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 $110,000 — $150,000 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.