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Technical Advisor to CTO

Job in Toronto, Ontario, C6A, Canada
Listing for: PENN Interactive
Full Time position
Listed on 2026-01-01
Job specializations:
  • IT/Tech
    Video Game
  • Entertainment & Gaming
    Video Game
Job Description & How to Apply Below
Position: Technical Advisor to the CTO
Join to apply for the  Technical Advisor to the CTO  role at  PENN Interactive
Join to apply for the  Technical Advisor to the CTO  role at  PENN Interactive
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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, the Score Bet Sports book & Casino, or the Score 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 the Score 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…
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