Technical Advisor to the CTO

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, , or 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 PENN Interactive is seeking an exceptional Technical Advisor to the CTO—a newly created, high‑impact role reporting directly to our CTO. As the first and only Technical Advisor, you will serve as a trusted partner and strategic extension of the CTO, helping to shape the future of our technology and products. You will be generating research, synthesizing insights into specific technical domains, doing hands‑on prototyping & technical exploration, driving initiatives that span across the organization, and helping multiple teams to move towards common goals across the Interactive group. The role requires tight coordination and collaboration with leaders across the org within Engineering, Product, Design, Strategy, and more. You will work across these teams toward a common vision and then facilitate planning and execution for the space across the interactive group. 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. About the Work You will conduct research to synthesize key opportunities, issues, and progress to date. Generate briefs that synthesize shared and divergent points of view and positions. The scope may vary from small investigations to substantial areas. Drive projects that require collaboration from multiple teams across the Interactive division while sharing a common strategic vision. Help teams evolve their understanding of a new Penn Interactive culture of engineering, in partnership with engineering leadership. Produce reading material for the CTO and executive leaders with summations, highlighted focus areas for deep processing, and prioritized order of consuming these reading materials. The reading will include the synthesis of a broad range of materials (academic research, business media & consultancies reports, white papers of internal teams, etc.). Engage with CTO on iterative investigations and prototyping as needed. Drill down into technical areas based on the CTO’s request and personal sense of company priorities/market trends. Create and maintain iterative mini‑brainstorms to ensure alignment with CTO thought leadership and just‑in‑time fluidity of investigation efforts. Produce a range of recommendations to the CTO based on research. Those may range from vision to individual solutions, depending on the topic, scope, and complexity. About You You will have demonstrated expertise in research, engineering and product development. You will be acknowledged as a deep expert in technical domains with a reputation as a credible thought leader. 15+ years of Software Engineering experience is required. Experience building consumer facing platforms, using bleeding‑edge technologies. Master's or PhD in Computer Science or related Engineering fields is preferred. Experience working closely with executive leaders. Proven customer facing experience - Startup experience considered an asset. Proven ability to navigate large organizations and to influence/inspire peers in engineering and product development. Works through high levels of ambiguity and drives clarity to senior leadership. Thorough understanding of cloud computing, cloud data center design, and distributed solution needs in high scale scenarios. Demonstrated ability to work through biases and preconceived notions through systemic, disciplined research and investigations. Able to pursue breakthrough thinking by assessing established and emerging thought leadership. Able to build bridges and assist the CTO with developing relationships with external industry and academic thought leaders; develop and maintain own relationships. Strong communication style that conveys expertise, clarity, and confidence. Track record of speaking externally is considered an asset. 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 Candidates residing in Ontario requiring special accommodation can email #J-18808-Ljbffr