Technical Advisor to the CTO

1 week ago


Toronto Montreal Calgary Vancouver Edmonton Old Toronto Ottawa Mississauga Quebec Winnipeg Halifax Saskatoon Burnaby Hamilton Surrey Victoria London Halton Hills Regina Markham Brampton Vaughan Kelowna Laval Southwestern Ontario R, Canada PENN Interactive Full time

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 & TeamPENN 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 WorkYou 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 & consultancy 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 YouYou 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.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 OfferCompetitive compensation package.Fun, relaxed work environment.Education and conference reimbursements.Parental leave top-up.Opportunities for career progression and mentoring others.#LI-REMOTEPenn 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.Create a Job AlertInterested in building your career at Penn Interactive? Get future opportunities sent straight to your email.Accepted file types: pdf, doc, docx, txt, rtfEnter manuallyAccepted file types: pdf, doc, docx, txt, rtfLinkedIn ProfileWebsiteWhat are your salary expectations?Are you legally authorized to work in Canada for Penn Entertainment or its affiliates? * Select...Penn Entertainment does not sponsor applications for work permits, provincial nomination, or permanent residence. #J-18808-Ljbffr



  • Toronto, Montreal, Calgary, Vancouver, Edmonton, Old Toronto, Ottawa, Mississauga, Quebec, Winnipeg, Halifax, Saskatoon, Burnaby, Hamilton, Victoria, Surrey, London, Halton Hills, Regina, Markham, Brampton, Vaughan, Kelowna, Laval, Southwestern Ontario, R, Canada FutureSight Inc. Full time

    A leading WealthTech venture studio is seeking a Founding CTO to pioneer a B2B AI copilot for financial advisors. You will own the technical vision, drive product development, and enhance advisor experiences. Ideal candidates are experienced founders with a passion for AI and the skills to lead technical teams. Join us in building an innovative solution for...

  • Field CTO

    4 weeks ago


    Canada Creek, Toronto, Montreal, Calgary, Vancouver, Edmonton, Old Toronto, Ottawa, Mississauga, Quebec, Winnipeg, Halifax, Saskatoon, Burnaby, Hamilton, Victoria, Surrey, Halton Hills, London, Regina, Markham, Brampton, Vaughan, Kelowna, Laval, Southwest 3Pillar Global Full time

    Field CTO 3Pillar Global builds breakthrough software products that power digital businesses. As we continue to expand our business, 3Pillar is seeking an experienced and dynamic Field CTO to provide (a) thought leadership, consult on strategic customer and partner engagements as billable engagements, (b) help the sales organization on key focus areas with...

  • Founding CTO

    4 weeks ago


    Montreal, Toronto, Calgary, Vancouver, Edmonton, Old Toronto, Ottawa, Mississauga, Quebec, Winnipeg, Halifax, Saskatoon, Burnaby, Hamilton, Victoria, Surrey, Halton Hills, London, Regina, Markham, Brampton, Vaughan, Kelowna, Laval, Southwestern Ontario, R, Canada GuruLink Full time

    Location: REMOTE / Montreal, QuebecThis job allows you to work remotely.Our client is a venture studio, looking for a founding CTO for a new company they are launching.The new venture is disrupting the building industry, helping to connect supply and demand.This venture is already significantly de-risked: they have validated market demand with 40+ experts...


  • Kelowna, Toronto, Montreal, Calgary, Vancouver, Edmonton, Old Toronto, Ottawa, Mississauga, Quebec, Winnipeg, Halifax, Saskatoon, Burnaby, Hamilton, Victoria, Halton Hills, Surrey, London, Regina, Markham, Brampton, Vaughan, Laval, Southwestern Ontario, W, Canada Block Rewards Full time

    About Block RewardsBlock Rewards is a pioneering startup revolutionizing employee benefits by enabling employers to offer bitcoin-based compensation, attracting top talent with innovative and high-value rewards. As we scale our client-facing platform, we are seeking a visionary Chief Technology Officer (CTO) to lead our technical strategy, ensure robust...

  • CTO/VP of Engineering

    4 weeks ago


    Toronto, Montreal, Calgary, Vancouver, Edmonton, Old Toronto, Ottawa, Mississauga, Quebec, Winnipeg, Halifax, Saskatoon, Burnaby, Hamilton, Victoria, Surrey, Halton Hills, London, Regina, Markham, Brampton, Vaughan, Kelowna, Laval, Southwestern Ontario, R, Canada MLabs Full time

    3 days ago Be among the first 25 applicants Get AI-powered advice on this job and more exclusive features. CTO/Engineering Lead - Solana ZK Computation Framework Location: Remote - North America/Asia preferred - Not a must though Compensation: $200K - $225K We are building the first Solana-native verifiable computation framework designed to accelerate the...


  • Toronto, Montreal, Calgary, Vancouver, Edmonton, Old Toronto, Ottawa, Mississauga, Quebec, Winnipeg, Halifax, Saskatoon, Burnaby, Hamilton, Victoria, Surrey, Halton Hills, London, Regina, Markham, Brampton, Vaughan, Kelowna, Laval, Southwestern Ontario, R, Canada MLabs Full time

    A leading technology company is seeking a CTO/Engineering Lead to develop a Solana-native verifiable computation framework. This role involves technical leadership, system architecture, and optimization of backend systems. Ideal candidates will have significant experience with Rust and Solana infrastructure, alongside strong DevOps skills. The position...


  • Laval, Toronto, Montreal, Calgary, Vancouver, Edmonton, Old Toronto, Ottawa, Mississauga, Quebec, Winnipeg, Halifax, Saskatoon, Burnaby, Hamilton, Surrey, Victoria, London, Halton Hills, Regina, Markham, Brampton, Vaughan, Kelowna, Southwestern Ontario, R, Canada Intact Full time

    IT technical Advisor - Digital WorkspaceJoin to apply for the IT technical Advisor - Digital Workspace role at IntactContinue with Google Continue with GoogleIT technical Advisor - Digital Workspace1 week ago Be among the first 25 applicantsJoin to apply for the IT technical Advisor - Digital Workspace role at IntactGet AI-powered advice on this job and more...

  • CTO, BlueChip Enable

    12 hours ago


    Toronto, Canada R-LABS Canada Inc. Full time

    Join to apply for the CTO, BlueChip Enable role at R-LABS Canada Inc. At R-LABS Canada Limited Partnership (“R-LABS”), we build purpose driven companies to solve major problems in real estate and housing. We are launching our next innovative company, BlueChip Enable (currently in stealth mode). To do so, we need an innovative CTO to partner with us to...

  • CTO, BlueChip Enable

    19 hours ago


    Toronto, Canada R-LABS Canada Inc. Full time

    Join to apply for the CTO, BlueChip Enable role at R-LABS Canada Inc. At R-LABS Canada Limited Partnership (“R-LABS”), we build purpose driven companies to solve major problems in real estate and housing. We are launching our next innovative company, BlueChip Enable (currently in stealth mode). To do so, we need an innovative CTO to partner with us to...

  • CTO, BlueChip Enable

    9 hours ago


    Toronto, Canada R-LABS Canada Inc. Full time

    Join to apply for the CTO, BlueChip Enable role at R-LABS Canada Inc. At R-LABS Canada Limited Partnership (“R-LABS”), we build purpose driven companies to solve major problems in real estate and housing. We are launching our next innovative company, BlueChip Enable (currently in stealth mode). To do so, we need an innovative CTO to partner with us to...