Director of AI and IT Operations

Full Description

Job Type

Full-time

Description

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 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 Overview

The Director of AI and IT Operations will be responsible for overseeing 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 AI technologies as well as Cloud and Data Center operations and other enterprise software applications . This leader also requires a deep technical foundational capability to accelerate and optimize all IT initiatives, creating AI Agents across our organization.

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, end-user support - enhancing performance, resilience, and decision-making across all IT domains.

Key Responsibilities

Strategic 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.

Benefits: Guideline 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 Account

• STD, Life, LTD and AD&D

• 401(k) with a company match program

• Unlimited Paid Time Off (PTO)

• Paid Parental Leave

• Commuter Benefits

• Employee Recognition Program

• Referral Bonus Program

Equal Opportunity Employer: Guideline 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.

Requirements

• 2-5 years of experience in using AI technologies in a B2B environment

• Completely knowledgeable in AI Agent Technologies, LLM modes and other AI tools that business use to drive outcomes

• Experience in a similar leadership role

• Proficiency 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 technologies.

• Demonstrated success implementing IT automation and scripting (PowerShell, Python, Ansible), ideally augmented by AI-driven orchestration.

• Strong understanding of modern security best practices and tools enhanced by AI threat detection.

• Excellent leadership, communication, and interpersonal skills.

• Strategic mindset with a passion for emerging technologies, continuous improvement, and AI innovation.