Chief AI and Technology Officer

Location: Brooklyn, NY
Employment Type: Full-Time
Schedule: Monday through Friday – Standard Business Hours
Salary: Based on Experience

We are building an AI-native heavy equipment rental business on the East Coast. By combining an established operating rental business with a proprietary technology platform focused on fleet optimization, predictive maintenance, dynamic pricing, and data-driven customer acquisition, we are scaling toward a multi-location regional network.

We are seeking a Chief AI & Technology Officer to build and lead the AI-native platform at the heart of our business. This is a highly strategic and hands-on leadership role focused on developing the technology infrastructure that powers fleet optimization, predictive maintenance, dynamic pricing, and data-driven customer acquisition.

The ideal candidate is both a builder and a leader — someone who can architect systems from the ground up while recruiting and managing a high-performing engineering organization.

• Architect, develop, and deploy AI and machine learning platforms for fleet utilization optimization, demand forecasting, and predictive maintenance
• Design and build data pipelines that ingest and analyze public permit and construction-related datasets to identify active project opportunities
• Develop dynamic pricing models that optimize rental rates based on demand, geography, seasonality, and competitive market conditions
• Lead technology strategy, platform architecture, infrastructure decisions, and system integrations
• Oversee IoT integrations, data collection systems, and third-party technology partnerships
• Recruit, build, and manage a high-performing engineering and data science team
• Collaborate closely with executive leadership to align technology initiatives with business growth objectives
• Establish best practices for software development, machine learning operations, data governance, and security

• 8+ years of experience in software engineering, artificial intelligence, machine learning, or related technical leadership roles
• Proven experience building and deploying production‑grade machine learning systems
• Strong background in data engineering, forecasting, optimization, and large‑scale analytics platforms
• Experience developing scalable cloud‑based applications and data infrastructure
• Knowledge of machine learning frameworks and modern AI technologies
• Experience in logistics, fleet management, supply chain, marketplaces, or related industries is highly preferred
• Strong leadership, communication, and team‑building skills
• Entrepreneurial mindset with the ability to operate effectively in a fast‑paced, high‑growth environment
• A hands‑on builder who enjoys solving complex problems while leading teams