Senior Director of Engineering Strategy & Delivery

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 ESPN BET, Hollywood Casino, theScore Bet Sportsbook & Casino, 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 

The Senior Director of Engineering Strategy & Delivery plays a crucial role in collaborating with Engineering, Product Management, Project Management, Technical Compliance, and other stakeholders to identify long-term platform capabilities and drive alignment across all teams. The goal is to establish a shared understanding and strategy to provide platform capabilities that will enable the user benefits of tomorrow. 

You will help develop and foster the long-term vision across engineering groups that aligns with the strategic vision of engineering and product leadership and business stakeholders. You will provide hands-on assistance to drive program definitions for large cross-functional programs, enabling the development of clear goals for the project teams. Additionally, you will work with senior leadership to identify and work towards shared objectives and key results, enabling the measurement of successful outcomes of the shared vision. 

You will also oversee the Release Management team to ensure seamless and timely software releases across the company. Furthermore, you will be responsible for driving operational efficiencies and cost savings within the engineering department, overseeing vendor relationships and contracts, and ensuring compliance with regulations by working closely with the PENN Interactive’s Technical Compliance organization. 

About the Work 

As a key member of our team you will: 

• Collaborate with Engineering, Product Management, Project Management, Technical Compliance, and other stakeholders to identify long-term platform capabilities. 
• Foster a long-term vision across engineering groups that aligns with the strategic vision of engineering and product leadership and business stakeholders. 
• Drive program definitions for large cross-functional programs, enabling the development of clear goals for project teams. 
• Work with senior leadership to identify key performance indicators (KPIs) to measure the successful outcomes of long-term goals. 
• Oversee the Release Management organization to ensure seamless and timely software releases. 
• Plan and schedule software releases, coordinating with various teams to define scope, timeline, and resources. 
• Manage the entire release lifecycle, ensuring that all necessary steps are followed, and issues are addressed promptly. 
• Maintain version control to ensure correct versions are released and updates or patches are applied correctly. 
• Ensure software meets quality standards before release by coordinating thorough testing and validation. 
• Identify and mitigate potential risks associated with releases. 
• Communicate release schedules, status, and issues to all stakeholders. 
• Maintain detailed documentation of the release process, including release notes and deployment instructions. 
• Monitor software post-release to ensure proper functionality and address any arising issues.
• Drive efficiency and cost savings within the engineering department.
• Oversee vendor relationships and contracts to ensure alignment with business goals and cost-efficiency.
• Work with the internal Technical Compliance organization to ensure software releases comply with regulations 

About You 

• This leader must have a strong senior presence, communicate effectively with internal and external stakeholders, and foster a can-do culture that aligns resources, priorities, and processes for success. 
• 15+ years of Technical Program Management, Product Management, or Software Engineering experience is required. 
• Demonstrated expertise in research, engineering, and product development. 
• Master's or PhD in Computer Science or related Engineering field is preferred. 
• Experience as a manager in engineering, technology product management, or technical program management is required. 
• Proven customer-facing experience; startup experience is considered an asset. 
• Proven ability to navigate large organizations and influence peers in engineering and product development. 
• Thorough understanding of cloud computing, cloud data center design, and distributed solution needs in high-scale scenarios. 
• Strong communication style that conveys expertise, clarity, and confidence. 

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. 
  
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Recently being recognized as a top workplace in the United States, we believe people work their best when they can be themselves. We are looking for hungry, innovative thinkers to help us challenge the status quo of the gaming industry.  Diversity, equity, and inclusion are vital to all of our processes, programs, and structures. Your story, who you are, and your experience matter here.