Senior AI Product Manager

Landmark is seeking a Senior AI Product Manager to serve as an individual contributor and lead its AI support product suite, including Homepilot, Staci, and Hillary. The role blends day-to-day product work with hands-on technical readiness, grounded in real user workflows and close collaboration with two AI engineers and the Head of Product. Based in the Presidio office in San Francisco, this position is focused on end users, evaluations, and commercialization across companies.

What you will do

• Shadow support teams and end users to understand operational details behind key product decisions.
• Build strong working relationships with the people using and relying on these tools.
• Work directly with prompts and evaluations as part of improving product performance.
• Review real interactions, investigate failure cases, and partner with engineering and operators to raise product quality.
• Convert learnings into practical product improvements.
• Design, prototype, and test with users, then iterate based on real workflows.
• Own the technical readiness roadmap, moving beyond a current Zendesk setup to connect with different email providers and CRM systems.
• Plan for the operational changes required to support multiple property management systems (PMS).
• Create a playbook to onboard acquired companies and external SaaS customers quickly.
• For each company, learn how they operate, then configure, train, evaluate, and calibrate Homepilot and the agents to match their processes.
• Collaborate directly with Drew on commercialization strategy, while owning the product roadmap needed to enable it.
• Work closely with two engineering partners, contribute to hands-on product design, and use AI to prototype and ship some code yourself.

What you bring

• 5+ years of Product Management experience.
• Operational depth: experience building tools for support or service teams and working with complex operations.
• Technical range: comfort with SQL, prompts and evaluations, APIs and integrations, and building prototypes.
• Experience using AI to extend what you can do, including shipping some code.
• Product design skills: ability to translate operational needs into usable experiences and work through designs with users and engineers.
• Close stakeholder partnership: willingness to go deep with end users, communicate priorities clearly, and follow through from discovery to delivery.
• AI experience (preferred): hands-on AI product experience is a plus, not required.

Tools and systems

• SQL
• Prompts and evaluations
• APIs and integrations
• Zendesk
• Email providers
• CRM systems
• Property management systems (PMS)

Compensation and work model

• Annual base salary: USD $180,000–$220,000
• Equity: competitive
• Location: Presidio office, San Francisco
• Work model: four days per week in the Presidio office, with some flexibility