Technical Advisor to the CTO

PENN Interactive; Toronto; On-site; CAD 120,000 - 160,000; Full time

Job summary

A leading entertainment technology firm in Toronto is seeking a Technical Advisor to the CTO. This key role involves driving technical initiatives across teams, conducting in-depth research, and synthesizing insights for executive leadership. Ideal candidates will have over 15 years of software engineering experience, strong communication skills, and expertise in cloud computing. The position offers a competitive compensation package in a collaborative and innovative work environment.

Benefits

Competitive compensation package

Fun, relaxed work environment

Education and conference reimbursements

Parental leave top-up

Opportunities for career progression

Qualifications

• 15+ years of Software Engineering experience required.
• Experience working closely with executive leaders.
• Proven customer-facing experience.
• Demonstrated ability to work through biases.
• Strong communication style that conveys expertise.

Responsibilities

• Conduct research to synthesize opportunities and issues.
• Drive projects requiring collaboration from multiple teams.
• Produce reading material for the CTO and executive leaders.
• Engage in iterative investigations and prototyping.
• Produce recommendations to the CTO based on research.

Skills

Research expertise

Engineering knowledge

Communication skills

Cloud computing understanding

Ability to navigate ambiguity

Education

Master's or PhD in Computer Science or related Engineering fields

Job description

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

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 progressto 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 oniterative investigations and prototyping as needed. Drill down into technical areas based on the CTO’s requestand personal sense ofcompanypriorities/market trends. Create and maintain iterative mini-brainstorms to ensure alignment with CTO thought leadership and just-in-time fluidity of investigationefforts.
• Produce a range of recommendationsto 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 inresearch,engineering and product development. You will be acknowledgedas adeep expert in technical domains with a reputation as a credible thought leader.
• 15+ years of Software Engineeringexperienceis required.
• 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 abilityto navigate large organizations andto influence/inspire peers in engineering and product development. Works through high levels ofambiguity 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 notionsthrough systemic, disciplined research and investigations.
• Able to pursue breakthrough thinking by assessing established and emerging thought leadership.
• Able to build bridges and assist theCTO 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

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.

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