Chief AI and Technology Officer

Employment Type: Full-Time

Schedule: Monday through Friday – Standard Business Hours

Salary: Based on Experience Chief AI & Technology Officer

About the Company: 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.

The Role: 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.

What You'll Do: 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 What You Bring 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 environmentA hands‑on builder who enjoys solving complex problems while leading teams