Director of AI and IT Operations

3 days ago


Toronto, Canada Guideline Full time

Join to apply for the Director of AI and IT Operations role at GuidelineJoin to apply for the Director of AI and IT Operations role at GuidelineAbout Guideline.aiGuideline is a global leading advertising data and media planning technology provider. Our dedication lies in empowering marketers and advertising sellers worldwide with the most accurate and complete advertising spend and pricing data along with cutting-edge media planning tools. Join our team as we guide the top brands, agencies, and media owners in realizing a more intelligent media buying and selling landscape.Position OverviewThe Director of AI and IT Operations will oversee the company’s AI adoption for internal IT operations, ensuring the effective and efficient use of AI technologies across the organization. This role requires a leader with technical expertise in AI technologies as well as Cloud and Data Center operations and other enterprise software applications. This leader will create AI Agents across the organization to accelerate and optimize IT initiatives.The successful candidate will guide the implementation and integration of AI into all functions in the company including customer success, marketing, sales, finance, human resources, infrastructure monitoring, security operations, and end-user support — enhancing performance, resilience, and decision-making across all IT domains.Key ResponsibilitiesStrategic Planning and AI Enablement: Develop and implement IT strategies that align with company goals, with AI as a core enabler of innovation, operational efficiency, and intelligent decision-making. Identify AI tools and frameworks to automate IT processes, improve forecasting, and reduce technical debt.AI-Enhanced Infrastructure Management: Manage and maintain the company’s IT infrastructure, including Microsoft and VMware environments, leveraging AI for predictive maintenance, performance optimization, and resource scaling.Smart Networking: Design and manage resilient, secure network architecture while integrating AI-driven network analytics to detect anomalies, optimize traffic, and ensure high availability.AI-Supported Help Desk Operations: Lead the IT help desk team using AI tools such as virtual agents, automated ticket triaging, and sentiment analysis to elevate user support and satisfaction.Cybersecurity with AI: Develop and enforce AI-augmented security protocols to proactively identify, mitigate, and respond to threats using behavior analytics, automated alerts, and machine learning threat intelligence.IT Automation: Drive the adoption of AI-powered automation tools to streamline workflows, reduce manual interventions, and increase operational agility across infrastructure, cloud services, and end-user computing.Team Leadership: Recruit, develop, and mentor IT staff with an emphasis on upskilling in AI, data literacy, and automation to foster a forward-thinking, AI-literate IT culture.Vendor and AI Partner Management: Manage external vendors and AI solution providers, ensuring scalable, ethical, and cost-effective implementation of intelligent technologies.BenefitsGuideline offers full-time employees a comprehensive benefits package based on location. Some benefits may include, but are not limited to:Medical, Dental, Vision, Health Savings Account, Flexible Spending AccountSTD, Life, LTD and AD&D401(k) with a company match programUnlimited Paid Time Off (PTO)Paid Parental LeaveCommuter BenefitsEmployee Recognition ProgramReferral Bonus ProgramEqual Opportunity EmployerGuideline is an equal opportunity employer, committed to our diversity and inclusiveness. We will consider all qualified applicants without regard to race, color, nationality, gender, gender identity or expression, sexual orientation, religion, disability, or age. We strongly encourage women, people of color, members of the LGBTQIA community, people with disabilities, and veterans to apply.Requirements2-5 years of experience in using AI technologies in a B2B environmentCompletely knowledgeable in AI Agent Technologies, LLM models and other AI tools used to drive outcomesExperience in a similar leadership roleProficiency in Microsoft technologies (Windows Server, Active Directory, Office 365, Azure)Proven knowledge of AI tools and their application in infrastructure, security, and user support (e.g., Microsoft Copilot, AI-based monitoring, or LLM-based automation)In-depth knowledge of VMware virtualization technologiesDemonstrated success implementing IT automation and scripting (PowerShell, Python, Ansible), ideally augmented by AI-driven orchestrationStrong understanding of modern security best practices and tools enhanced by AI threat detectionExcellent leadership, communication, and interpersonal skillsStrategic mindset with a passion for emerging technologies, continuous improvement, and AI innovation #J-18808-Ljbffr



  • Toronto, Canada Guideline Full time

    Join to apply for the Director of AI and IT Operations role at Guideline Join to apply for the Director of AI and IT Operations role at Guideline About Guideline.ai Guideline is a global leading advertising data and media planning technology provider. Our dedication lies in empowering marketers and advertising sellers worldwide with the most accurate and...


  • Toronto, Canada Guideline, Inc. Full time

    OverviewGuideline is a global leading advertising data and media planning technology provider. Our dedication lies in empowering marketers and advertising sellers worldwide with the most accurate and complete advertising spend and pricing data along with cutting-edge media planning tools. Join our team as we guide the top brands, agencies, and media owners...


  • Toronto, Canada Guideline, Inc. Full time

    Overview Guideline is a global leading advertising data and media planning technology provider. Our dedication lies in empowering marketers and advertising sellers worldwide with the most accurate and complete advertising spend and pricing data along with cutting-edge media planning tools. Join our team as we guide the top brands, agencies, and media owners...


  • Toronto, Ontario, Canada Guideline Full time

    Job TypeFull-timeDescriptionAbout Guideline is a global leading advertising data and media planning technology provider. Our dedication lies in empowering marketers and advertising sellers worldwide with the most accurate and complete advertising spend and pricing data along with cutting-edge media planning tools. Join our team as we guide the top brands,...


  • Toronto, Canada Sun Life Full time

    Job Description :About the roleSun Life Canada is on an exciting journey of innovation and transformation to deepen our commitment to our One Sun purpose “To help clients achieve lifetime financial security and live healthier lives”. Sun Life Canada Operations includes a team of over 5,000 dedicated team members across Canada and SL Global Solutions in...


  • Toronto, Canada City of Toronto Full time

    Join to apply for the DIRECTOR CHANNEL OPERATIONS role at City of Toronto. Job ID: 59495 Job Category: Customer Service Division & Section: Customer Experience, CX Channel Operations Job Type & Duration: Full-time, 1 Permanent Vacancy Shift Information: Monday to Friday, 35 hours per week Affiliation: Non-Union Number of Positions Open: 1 Posting Period:...


  • Toronto, Canada City of Toronto Full time

    Join to apply for the DIRECTOR CHANNEL OPERATIONS role at City of Toronto . Job ID: 59495 Job Category: Customer Service Division & Section: Customer Experience, CX Channel Operations Job Type & Duration: Full-time, 1 Permanent Vacancy Shift Information: Monday to Friday, 35 hours per week Affiliation: Non-Union Number of Positions Open: 1 Posting Period:...


  • Toronto, Canada Rezolve Ai Full time

    Join to apply for the Sr. Product Marketing Manager (Hybrid/Remote) role at Rezolve Ai Join to apply for the Sr. Product Marketing Manager (Hybrid/Remote) role at Rezolve Ai Who we areRezolve Ai (NASDAQ: RZLV), is redefining retail with cutting-edge AI solutions that transform the shopping experience. As a leader in Product Discovery, we empower retailers...

  • AI Strategist

    2 weeks ago


    Toronto, Canada Siena AI Full time

    Meet Siena Siena is the first intelligence layer for customer experience. We’re creating an operating system of AI agents that learn, remember, and act across every customer touchpoint—from support conversations to shopping experiences to voice and social media interactions. Siena doesn’t just automate support; it powers shopping agents, builds...

  • AI Strategist

    1 week ago


    Toronto, Canada Siena AI Full time

    Meet Siena Siena is the first intelligence layer for customer experience. We’re creating an operating system of AI agents that learn, remember, and act across every customer touchpoint—from support conversations to shopping experiences to voice and social media interactions. Siena doesn’t just automate support; it powers shopping agents, builds...