Senior AI Product Manager

Senior AI Product Manager

Company & Role

At Landmark, we believe better living starts with exceptional experiences for owners, residents, and operating teams. Born out of the engineering labs at Bungalow, we’re reimagining property management from the ground up, building AI-native tools that make everyday operations better for the people doing the work and the people they serve.

We’re hiring a Senior AI Product Manager to lead our AI support product suite: Homepilot, our AI-native heads‑up display; Staci, our tenant support agent; and Hillary, our owner support agent. A strong initial product is already built. Now it’s time to formalize it, go deep on quality, and shape what comes next.

This is a hands‑on individual contributor role on a small, high‑caliber team. You’ll report directly to the Head of Product, partner with two AI engineers, and bring product judgment, design skills, and technical curiosity to the work. Half your time will be spent exceptionally close to end users and deep in evaluations. You’ll also own the technical readiness roadmap that helps these products work across companies and supports their commercialization.

Your Mission

• Go Where the Work Is: Shadow support teams and end users, learn their processes, and understand the operational details behind every product decision. Build close relationships with the people using and depending on these tools.
• Get Into the Details: Work hands‑on with prompts and evaluations. Examine real interactions, investigate failure cases, and partner with engineering and operators to improve product quality.
• Close the Feedback Loop: Translate what you learn into practical improvements. Design, prototype, test with users, and keep refining the experience against real workflows.

Build the Next Chapter

• Make the Suite Portable: Own the technical readiness roadmap to move beyond our current Zendesk setup and connect to different email providers and CRM systems. Account for the changes needed to support multiple property management systems (PMS).
• Make Onboarding Repeatable: Build a playbook to rapidly onboard acquired companies and external SaaS customers. Learn their processes and procedures, then configure, train, evaluate, and calibrate Homepilot and the agents for how each company works.
• Shape Commercialization: Partner directly with Drew on commercialization strategy, while owning the product roadmap required to make it possible.
• Build Alongside the Team: Work closely with your two engineering partners, contribute 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 supporting complex operations. You understand workflows, exceptions, and tradeoffs well enough to earn operators’ trust and make strong product decisions.
• Technical Range: Comfortable with SQL, prompts and evaluations, APIs and integrations, and building prototypes. You use AI to extend what you can do, including shipping some code.
• Product Design Skills: You can turn operational needs into clear, usable experiences and work through designs directly with users and engineers.
• Close Stakeholder Partnership: You get into the details 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 a prerequisite. We’re also interested in an exceptional operationally focused PM ready to go deep on AI.
• Perks + Parameters

Details:

• Annual base salary: $180,000–$220,000 USD
• Equity: Competitive
• Location: Presidio office, San Francisco
• Work model : Four days per week in our Presidio office, with some flexibility.