Head of AI

Context

At Landmark, we believe better living starts with exceptional experiences for owners, residents, and operating teams. Born out of the engineering labs at Bungalow, Landmark is reimagining property management from the ground up. Landmark is building a future where AI and human expertise work together to deliver higher quality, more consistent and faster service. As we scale, we're seeking a Head of AI to lead our engineering organization and shape the future of our platform.

As the executive leading both AI and engineering, you will define the architecture, systems, and technical vision that power our platform, building a world-class team and setting the bar for excellence across disciplines. You will translate vision into action, building the systems, team, and technical rigor needed to scale our AI capabilities and deliver real impact for customers.

You will own and drive :

• Building and leading a world-class AI and engineering team
• Cross-functional alignment on Landmark's AI-first strategy
• The architectural framework that blends automatic workflows with agentic capabilities
• AI strategy and implementation across semantic search and multi-system data integration
• Proactive touchpoints that deepen engagement with our customers before issues arise
• Multi-agent system design enabling end-to-end workflow automation
• Continual innovation in multi-agent systems supporting the property lifecycle
• And more…

Your Mission

Strategic AI Leadership : Own, define, and execute our AI strategy in service of Landmark's AI-first product vision. Evaluate opportunities, prioritize strategic projects, and ensure alignment with business objectives and long-term technical architecture.

Build & Scale a World-Class Team : Recruit, develop, and lead a world-class AI and engineering organization. Build the culture, technical rigor, and operational excellence needed to execute at scale, fostering an environment that blends cutting edge tools & frameworks with pragmatic feature delivery.

Engineering Infrastructure : Define best practices and own infrastructure decisions for robust, secure, and scalable deployment across our engineering team with a focus on AI services. Oversee related containerization (Docker) and cloud deployment processes, ensuring observability, reliability, performance, and maintainability.

AI System Leadership : You will oversee the design of systems that continuously learn from data, streamline operations, and improve resident and owner experiences. From automation frameworks to semantic understanding, you will ensure Landmark's AI platform is reliable, scalable, and transformative.

Cross-Functional Collaboration : You will work cross-functionally with product, operations, and leadership to prioritize high-leverage AI initiatives. You willl translate business needs into intelligent systems that create measurable outcomes

Frontier Leadership : Ensure the organization stays ahead of AI advancements by cultivating experimentation and thought leadership. Champion AI adoption across the business, partnering with teams beyond engineering to identify high-impact applications and embed intelligent workflows throughout Landmark's operations. Your work will keep Landmark at the frontier of AI-powered operations and product innovation

Minimum Viable Skillset

Experience :

Perks + Parameters

The Stack