[Hiring] Senior Technical Program Manager, Intelligent Automation @Penn Interactive

Role Description

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.

Qualifications

• 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.

Benefits

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

Salary Range

$110,000 — $150,000 CAD

Company Description

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.